顺式-1,3-二氯丙烯 | 10061-01-5

• 物质功能分类: 化学试剂 - 有机试剂 - 卤代脂肪烃
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 顺式-1,3-二氯丙烯
• 中文别名: 顺-1,3-二氯丙烯
• 英文名称: (Z)-1,3-dichloropropene
• 英文别名: cis-1,3-Dichloropropene；(Z)-1,3-dichloroprop-1-ene
• CAS: 10061-01-5
• 化学式: C₃H₄Cl₂
• 分子量: 110.971
• InChiKey: UOORRWUZONOOLO-UPHRSURJSA-N

物化性质

• 熔点：
  -50 °C
• 沸点：
  104 °C(lit.)
• 密度：
  1.225 g/mL at 25 °C(lit.)
• 闪点：
  75 °F
• 溶解度：
  可溶于氯仿、甲醇（微量）
• 暴露限值：
  ACGIH TLV: TWA 1 ppm for cis and trans isomers (adopted).
• LogP：
  1.82 at 20℃ and pH5.83-7.78
• 表面张力：
  69.6mN/m at 976.8mg/L and 20.2℃
• 物理描述：
  Cis-1,3-dichloro-1-propene is a colorless to amber liquid with a sweetish odor. (NTP, 1992)
• 颜色/状态：
  COLORLESS LIQUID
• 气味：
  CHLOROFORM-LIKE ODOR
• 蒸汽密度：
  1.4 AT 37.8 °C (AIR= 1)
• 蒸汽压力：
  26.3 mm Hg @ 20 °C
• 亨利常数：
  0.00 atm-m3/mole
• 大气OH速率常数：
  1.12e-11 cm3/molecule*sec
• 分解：
  When heated to decomposition it emits toxic fumes of /hydrogen chloride/.
• 折光率：
  Index of refraction: 1.4730 @ 20 °C
• 保留指数：
  721.4;706.7;714.2;719.8;723.5;724
• 稳定性/保质期：
  稳定但易燃，与强氧化剂、铝及其合金、活性金属、卤素以及某些金属盐 incompatible。可能对光敏感。

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  5
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

ADMET

代谢

cis-1,3-二氯丙烯((Z)-DCP)通过谷胱甘肽结合进行解毒在老鼠体内进行了研究。给2只老鼠口服20mg/kg的放射性标记的顺式-二氯丙烯。在2天内，每天收集尿液和粪便，并分析其放射性。在尿液中，82-84%的放射性物质在24小时内被回收。大部分物质以N-乙酰-S-顺式-3-氯丙烯基)半胱氨酸形式存在。当顺式-二氯丙烯与谷胱甘肽和老鼠肝细胞质一起孵化时，10分钟内回收率为81%。体外反应的产物是S-(顺式-3-氯丙烯基)谷胱甘肽。细胞质和肝脏上清液中谷胱甘肽的存在是去除顺式-二氯丙烯所必需的，/结果显示/，用放射性标记的顺式-二氯丙烯处理的老鼠体内放射性物质的快速消除是由于有效的依赖于谷胱甘肽的生物转化。

Detoxication of cis-1,3-dichloropropene ((Z)-DCP) by glutathione conjugation was studied in the rat. 2 rats were given an oral dose of 20 mg/kg radiolabeled cis-dichloropropene. Urine & feces were collected daily for 2 days & analyzed for radioactivity. In the urine, 82-84% of the radioactive material was recovered within 24 hr. Most of this material was present as N-acetyl-S-cis-3-chloroprop-2-enyl)cysteine. When cis-dichloropropene was incubated with glutathione & rat liver cytosol, 81% was recovered in 10 min. The product of the in vitro reaction was S-(cis-3-chloroprop-2-enyl) glutathione. The presence of glutathione in cytosol & liver supernatant was necessary to remove cis-dichlopropene the /results indicate/ that the rapid elimination of radioactivity from rats dosed with radiolabeled cis-dichloropropene is due to an efficient glutathione dependent biotransformation.

来源:Hazardous Substances Data Bank (HSDB)

代谢

已显示，顺-1,3-二氯丙烯的一个次要代谢途径是单加氧酶催化的氧化，可能导致代谢物顺-1,3-二氯丙烯氧化物形成的可能性。

It has been shown that a minor metabolic pathway of the cis-1,3-dichloropropene is mono-oxygenase catalyzed oxygenation, leading to the possible formation of the metabolite cis-1,3-dichloropropene-oxide.

来源:Hazardous Substances Data Bank (HSDB)

代谢

3-9只体重在200-260克的雄性Fischer 344大鼠被分组，通过灌胃方式给予50毫克顺式-1,3-二氯丙烯（含94.1%顺式和2.5%反式）或50毫克反式-1,3-二氯丙烯（含97.3%反式和0.8%顺式）/每千克体重。在大鼠给药后不同时间点将其处死，以测定肝脏、肾脏、前胃、腺胃、胃和膀胱中的组织非蛋白巯基（NPS）。同时采集血液样本以确定未改变的1,3-二氯丙烯的存在。顺式-1,3-二氯丙烯仅在给药后15分钟的血液中检测到（6.58微克/升），而反式-1,3-二氯丙烯的血液水平在给药后15分钟和45分钟分别为11.72和8.38微克/升。肝脏、肾脏、前胃和腺胃的非蛋白巯基含量显著减少，这种减少在大约给药后2小时达到最大值。膀胱中没有观察到减少。由于没有报告单个对映异构体的结果，因此无法区分顺式和反式-1,3-二氯丙烯对NPS的影响。结果表明，口服给药1,3-二氯丙烯会在大鼠体内迅速且显著地减少组织的非蛋白巯基含量。

Groups of 3-9 male Fischer 344 rats (200-260g) were admin 50 mg cis-1,3-dichloropropene (94.1% cis- & 2.5% trans-) or 50 mg trans-1,3-dichloropropene (97.3% trans- & 0.8 cis-)/kg bw, by gavage. The rats were sacrificed at various intervals after dosing, to determine the tissue non-protein sulfhydryls (NPS) in the liver, kidneys, forestomach, glandular, stomach, & bladder. Blood samples were also taken to determine the presence of unchanged 1,3-dichloropropene. Cis-1,3-dichloropropene was only detected in the blood (6.58 ug/liter) 15 min after dosing, the blood levels of trans-1,3-dichloropropene were 11.72 & 8.38 ug/liter, respectively, 15 & 45 min after dosing. A statistically significant decr in the non-protein sulfhydryl contents of the liver, kidneys, forestomach, & glandular stomach was found. This depletion reached a max, approx 2 hr after dosing. No depletion was noted in the bladder. It is not possible to distinguish the effects of cis- & trans-1,3-dichloropropene on NPS, as the results for the individual isomers were not reported. The results indicated that orally admin 1,3-dichloropropene produces a rapid & significant depletion of tissue non-protein sulfhydryls in the rat.

来源:Hazardous Substances Data Bank (HSDB)

代谢

对雄性Wistar大鼠腹腔注射Z-异构体和E-异构体的1,3-二氯丙烯的生物转化进行研究，以产生含硫产品。通过使用带有氮和硫选择性检测的气相色谱（GC-NDP和GC-FDP）以及带有负化学电离和单离子检测的GC/MS，确定动物尿液中巯基尿酸的存在。通过使用GC-NDP和GC-FPD，对以5微克剂量处理的二氯丙烯异构体的动物尿液中的巯基尿酸进行了量化，而GC/负化学电离/MS仅检测到由25微克或更高剂量产生的巯基尿酸，因为内源性产物的干扰。测试的两种产品都通过谷胱甘肽结合代谢，生成2种主要的巯基尿酸结合物，并且测试的所有三种分析程序都有助于确定人体对低水平1,3-二氯丙烯的暴露。

The biotransformation to sulfur containing products of the Z-isomers & E-isomers of 1,3-dichloropropene administered ip in combination to male Wistar-rats was investigated. The presence of mercapturic acids in the urine of the animals was determined using GC with nitrogen & sulfur selective detection (GC-NDP & GC-FDP, respectively) & GC/MS with negative chemical ionization & single ion detection. Quantification of mercapturic acids in the urine of animals treated with the dichloropropene isomers in doses of 5 ug each, was achieved with the use of GC-NDP & GC-FPD, while GC/negative chemical ionization/MS detected only the mercapturic acids generated by doses = 25 ug or higher, due to the interference of endogenous products. Both products tested are metabolized via glutathione conjugation, with the generation of 2 major mercapturic acid conjugates, & that all three analytical procedures tested are useful for the determination of human exposure to low levels of 1,3-dichloropropene.

来源:Hazardous Substances Data Bank (HSDB)

代谢

研究了在大鼠肾脏微体和从猪肝中纯化的含黄素的单加氧酶存在下，顺式和反式-1,3-二氯丙烯的半胱氨酸S-结合物的代谢。用孤立的大鼠肾脏细胞进行的初步研究表明，半胱氨酸S-结合物对细胞具有相当大的毒性，这一过程与含黄素的单加氧酶在肾毒素生物激活中的作用一致。合成了半胱氨酸S-结合物的假定的S-氧化物代谢物，并通过光谱方法分离和鉴定了对映体。通过比较代谢物的化学性质与合成的半胱氨酸S-结合物S-氧化物的化学性质，鉴定了半胱氨酸S-结合物的代谢产物。令人惊讶的是，在大鼠肾脏微体中没有观察到S-结合物S-氧化酶活性，但当半胱氨酸S-结合物与高度纯化的猪肝含黄素单加氧酶一起孵化时，这种活性存在。动力学参数表明，观察到了显著的S-氧化酶立体选择性 和结构选择性：顺式半胱氨酸S-结合物是首选底物，半胱氨酸S-结合物的N-乙酰化降低了底物活性。S-氧化反应显著地对映选择性，并且对于具有更高Vmax值的半胱氨酸S-结合物，对映选择性更大。半胱氨酸S-结合物S-氧化物并非永久稳定，在某些条件下，S-氧化物会发生(2,3)-sigma迁移重排形成丙烯醛。从S-(氯丙烯基)半胱氨酸结合物S-氧化物形成丙烯醛或其他亲电性产品可能有助于解释观察到的S-(氯丙烯基)半胱氨酸结合物的肾效应。因此，用半胱氨酸S-结合物处理的大鼠近端小管细胞或LLC-PK1细胞的细胞毒性研究表明，细胞活力随时间和剂量的增加而下降。在存在甲巯咪唑（一种含黄素单加氧酶的替代底物竞争性抑制剂）的情况下，半胱氨酸S-结合物的肾脏细胞毒性降低，这表明该酶可能有助于1,3-二氯丙烯的肾脏效应。

The metabolism of cysteine S-conjugates of both cis- and trans-1,3-dichloropropene in the presence of rat kidney microsomes and purified flavin-containing monooxygenase from hog liver was investigated in vitro. Preliminary studies with isolated rat kidney cells demonstrated that cysteine S-conjugates were quite toxic to the cells in a process which was consistent with a role of the flavin-containing monooxygenase in the bioactivation of the nephrotoxins. Putative S-oxide metabolites of cysteine S-conjugates were chemically synthesized, and diastereomers were separated and identified by spectroscopic means. The metabolic products of cysteine S-conjugates were identified by comparing the chemical properties of the metabolites with authentic synthetic cysteine S-conjugate S-oxides. Surprisingly, S-conjugate S-oxygenase activity was not observed with rat kidney microsomes but was present when cysteine S-conjugates were incubated with the highly purified flavin containing monooxygenase from hog liver. The kinetic parameters indicated that considerable S-oxygenase stereoselectivity and structural selectivity was observed: cis cysteine S-conjugates were preferred substrates and N-acetylation of cysteine S-conjugates decreased substrate activity. S-Oxygenation was considerably diastereoselective and diastereoselectivity was much greater for cysteine S-conjugates with higher Vmax values. Cysteine S-conjugate S-oxides were not indefinitely stable, and under certain conditions, the S-oxides underwent a (2,3)-sigmatropic rearrangement to acrolein. Formation of acrolein or other electrophilic products from S-(chloropropenyl)cysteine conjugate S-oxides may contribute to the renal effects observed for S-(chloropropenyl)cysteine conjugates. Thus, cytotoxicity studies with isolated rat proximal tubular cells or LLC-PK1 cells treated with cysteine S-conjugates showed a time and dose-dependent decrease in cell viability. Reduction of renal cytotoxicity of cysteine S-conjugates in the presence of methimazole, an alternate substrate competitive inhibitor of the flavin containing monooxygenase, suggested that this enzyme may contribute to the renal effects of 1,3-dichloropropene.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

识别：1,3-二氯丙烯是一种无色至琥珀色液体，具有刺激性、刺激性强、氯仿般的气味。它已被广泛应用于农业中，作为一种种植前土壤熏蒸剂，用于控制蔬菜、土豆和烟草中的线虫。它通常作为包含1,2-二氯丙烷的混合物的一部分出现。主要应用方式是通过土壤注射。在水体中，1-3-二氯丙烯可能会迅速消失，因为它的水溶性相对较低，挥发性较高。人类暴露：普通人群通过空气、水或食物的暴露可能性不大。职业暴露可能通过吸入和皮肤接触。暴露后眼睛和上呼吸道粘膜的刺激症状会迅速出现。皮肤暴露会引起严重的皮肤刺激。吸入可能会导致严重的中毒症状和体征，较低剂量的暴露会导致中枢神经系统抑制和呼吸系统刺激。一些中毒事件中，有人因粘膜刺激、胸痛、头痛、恶心、呕吐、眩晕，偶尔还会出现意识丧失和性欲减退而住院治疗。研究了从事氯化三碳化合物生产的工人的生育状况与对照组进行了比较。没有迹象表明生育能力下降与暴露有关。动物研究：1,3-二氯丙烯在动物体内的急性口服毒性为中等至高。急性皮肤暴露具有中等毒性。急性中毒涉及中枢神经和呼吸系统。家兔皮肤和眼睛刺激试验中出现了严重反应。在小鼠和大鼠的吸入研究中，观察到嗅觉上皮的退化和增生。顺式和反式-1,3-二氯丙烯及其混合物在有和无代谢激活的细菌中具有诱变性。在小鼠中，观察到膀胱、前胃和鼻腔粘膜增生的发生率增加。良性肺肿瘤的发生率有所增加。在大鼠的嗅觉粘膜中也看到了一些毒性变化，但没有增加肿瘤发生率。1,3-二氯丙烯的主要代谢消除途径是与谷胱甘肽结合。

IDENTIFICATION: 1,3-Dichloropropene is a colorless to amber colored liquid with a penetrating, irritating, chloroform-like odor. It has been widely used in agriculture as a pre-plant soil fumigant for the control of nematodes in vegetables, potatoes, and tobacco. It often appears as part of a mixture also including 1,2-dichloropropane. Application is primarily by soil injection. In water, 1-3-dichloropropene is likely to disappear rapidly, because of its relatively low water solubility and high volatility. HUMAN EXPOSURE: The exposure of the general population through air, water, or food is unlikely. Occupational exposure is likely to be through inhalation and via the skin. Irritation of the eyes and the upper respiratory mucosa appears promptly after exposure. Dermal exposure caused severe skin irritations. Inhalation may result in serious signs and symptoms of poisoning with lower exposures resulting in depression of the central nervous system and irritation of the respiratory system. Some poisoning incidents have occurred in which persons were hospitalized with signs and symptoms of irritation of the mucous membrane, chest discomfort, headache, nausea, vomiting, dizziness and, occasionally, loss of consciousness and decreased libido The fertility status of workers employed in the production of chlorinated three-carbon compounds was compared with a control group. There was no indication of an assocation between decreased fertility and exposure. ANIMAL STUDIES: The acute oral toxicity of 1,3-dichloropropene in animals is moderate to high. Acute dermal exposure is moderately toxic. Acute intoxication showed central nervous and respiratory system involvement. Severe reactions were seen in rabbit skin and eye irritation tests. Degeneration of the olfactory epithelium and hyperplasia were seen in inhalation studies with mice and rats. Cis- and trans-1,3-dichloropropene and mixtures were mutagenic in bacteria with, and without, metabolic activation. In mice, increased incidences of hyperplasia of the urinary bladder, the forestomach, and the nasal mucosa were observed. There was an increase in the incidence of benign lung tumors. Some toxic changes in the olfactory mucosa of the nasal cavity were also seen in rats, but no increase in tumor incidence. The major metabolic route of elimination of 1,3-dichloropropene is via conjugation with glutathione.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 毒性总结

顺式-1,3-二氯丙烯的主要毒性效应是入口效应，这是由于该化合物的化学活性和其物理化学性质导致的。反复刺激会导致目标组织细胞增生反应。顺式-1,3-二氯丙烯的致突变性归因于它通过细胞色素P-450的生物转化，形成特异性的环氧化合物和3-氯-2-羟基丙醛的水解产物。谷胱甘肽的耗尽可能会阻断顺式-1,3-二氯丙烯的主要解毒途径，导致由于反应中间体与细胞中的大分子结合，从而增加肝脏和肾脏等器官的毒性。有一些证据表明，暴露于顺式-1,3-二氯丙烯的肝细胞毒性之前，磷脂过氧化氢水平会升高（L893）。

The primary toxic effects of cis-1,3-dichloropropene are portal-of-entry effects resulting from the chemical reactivity of the compound and its physicochemical properties. Repeated irritation results in a hyperplastic response in the target tissues. The mutagenicity of cis-1,3-dichloropropene is attributed to its biotransformation by cytochrome P-450 to stereospecific epoxides and the hydrolysis product, 3-chloro-2-hydroxypropanal. It is likely that depletion of glutathione would block the major detoxification pathway for cis-1,3- dichloropropene, resulting in increased toxicity of organs such as the liver and kidney because of binding of reactive intermediates to macromolecules in cells. There is some evidence that cytotoxicity of hepatic cells exposed to cis-1,3-dichloropropene is preceded by increased levels of phospholipid hydroperoxides (L893).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌性证据

A3：已确认的动物致癌物，对人类的相关性未知。/1,3-二氯丙烯/

A3: Confirmed animal carcinogen with unknown relevance to humans. /1,3-Dichloropropene/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：关于1,3-二氯丙烯的致癌性，没有可用的流行病学数据。混合异构体1,3-二氯丙烯（工业级）在实验动物中具有致癌性的证据是充分的。总体评估：1,3-二氯丙烯（工业级）可能对人类具有致癌性（2B组）。/1,3-二氯丙烯（工业级）/

Evaluation: No epidemiological data relevant to the carcinogenicity of 1,3-dichloropropene were available. There is sufficient evidence in experimental animals for the carcinogenicity of mixed isomers of 1,3-dichloropropene (technical grade). Overall evaluation: 1,3-Dichloropropene (technical grade) is possibly carcinogenic to humans (Group 2B). /1,3-Dichloropropene (technical grade)/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

3, 其对人类致癌性无法分类。

3, not classifiable as to its carcinogenicity to humans. (L135)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

在大鼠口服8.3-13.5 mg/kg体重的顺式或反式-2-(14)碳-1,3-二氯丙烯后，顺式异构体的80%放射性活性和反式异构体的57%放射性活性在24小时内通过尿液排出。在接下来的72小时内，几乎没有进一步的尿液排出。在96小时后，顺式异构体的2-5%和反式异构体的23-24%以(14)C，二氧化碳的形式呼出；其他放射性化合物的呼出量很少。观察到很少的粪便排出。两种异构体的回收率约为90%。

Following oral admin of 8.3-13.5 mg/kg bw cis- or trans-2-(14)carbon-1,3-dichloropropene to rats, 80% of the radioactivity of the cis-isomer & 57% of the radioactivity of the trans-isomer were excreted in the urine within 24 hr. Little further urinary excretion occurred over the next 72 hr. After 96 hr, 2-5% of the cis-isomer & 23-24% of the trans-isomer were expired as (14)C, Carbon dioxide; exhalation of other radioactive cmpds was minor. Little fecal excretion was observed. Recovery of both isomers was about 90%.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在大鼠口服标记有^(14)碳的1,2-二氯丙烷、顺式-1,3-二氯丙烯2或反式-1,3-二氯丙烯3之后，80-90%的放射性物质在前24小时内通过粪便、尿液和呼出的气体排出。尿液是这三种情况下的主要排泄途径。...

Following the oral admin to rats of (14)carbon-labeled 1,2-dichloropropane, cis-1,3-dichloropropene 2, or trans-1,3-dichloropropene 3, 80-90% of the radioactivity was eliminated in the feces, urine & expired air within the first 24 hr. The urine was the major route of excretion in all 3 cases. ...

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

老鼠被喂食了标记有(14)碳的1,3-二氯丙烯的异构体，并显示出它们在新陈代谢方面的差异。所有化合物中，有80-90%在最初的24小时内被排出。主要的排泄途径是通过尿液，其中发现了56.5%的反式异构体。排出的(14)二氧化碳的量是23.6%，相应地，尿液中排出的量较少。

... Rats were fed (14)carbon-labeled ... isomers of 1,3-dichloropropene & showed differences in their metab. With all cmpds, 80-90% was eliminated in the first 24 hr. Major route of excretion was in the urine, where ... 56.5% of trans was found. The amount of (14)carbon dioxide excreted was 23.6%, with correspondingly less ... in the urine.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

14C-cis和14C-trans-1,3-二氯丙烯（97%；62%顺式和38%反式）的命运在给雄性B6C3F1小鼠口服1或100 mg/kg体重（每个剂量水平3只动物）后进行了研究。在48小时后分析了尿液、粪便、呼出气体、组织和剩余尸体。尿液是主要的排泄途径，分别有63%和79%的给药剂量（1和100 mg/kg体重）在48小时内被排出。尿液排泄的半衰期在5-6小时之间。粪便和呼出的二氧化碳分别占14C放射性的15%和14%。在尸体中发现了2%。14C活性的组织浓度在胃壁中最高，其次是肾脏、肝脏、膀胱、脂肪和皮肤，依次递减...。

The fate of 14C-cis & 14C-trans-1,3-dichloropropene (97%; 62% cis & 38% trans) was studied after oral dosing of male B6C3F1 mice with 1 or 100 mg/kg bw (3 animals/dose level). Urine, feces expired air, tissues, & remaining carcasses were analyzed after 48 hr. Urine was the major route of excretion, with 63 & 79%, respectively, of the admin doses (1 & 100 mg/kg bw) being excreted over 48 hr. Half-lives for urinary excretion raged from 5-6 hr. Feces & expired /carbon dioxide/ accounted for 15 & 14% of the 14C-radioactivity, respectively. In the carcass, 2% was found. The tissue concns of 14C-activity were highest in the stomach wall, followed in decreasing order by kidneys, liver, bladder, fat, & skin ... .

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  3.2
• 危险品标志：
  T,N
• 安全说明：
  S36/37,S45,S60,S61
• 危险类别码：
  R20/21,R36/37/38,R43,R10,R50/53,R25
• WGK Germany：
  3
• 危险品运输编号：
  UN 2047
• 包装等级：
  III
• 危险类别：
  3.2
• 危险标志：
  GHS02,GHS06,GHS08,GHS09
• 危险性描述：
  H226,H301,H304,H311,H315,H317,H319,H332,H335,H410
• 危险性防范说明：
  P261,P273,P280,P301 + P310,P305 + P351 + P338,P312
• 储存条件：
  库房应保持通风、低温和干燥的环境，并采取轻装轻卸的操作方式。同时需将该物品与其他氧化剂和酸类分开存放，以确保安全。

SDS

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Section I.Chemical Product and Company Identification
Chemical Name cis-1,3-Dichloropropene
(1mg/ml in Methanol) [for Water Analysis]
Portland OR
Not available.
Synonym
Chemical Formula C3H4Cl2
CAS Number 10061-01-5
67-56-1 (Methanol)

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Section II. Composition and Information on Ingredients
CAS Number Percent (%) TLV/PEL Toxicology Data
Chemical Name
cis-1,3-Dichloropropene Ca. 0.13% This chemical is classified as a (Methanol)
10061-01-5
(1mg/ml in Methanol) [for Water Analysis] possible carcinogen. There is Rat LD50 (oral) 5600 mg/kg
67-56-1 (Methanol) Ca. 99.87% (Methanol)
no acceptable exposure limit for Rabbit LD50 (dermal) 15800 mg/kg
a carcinogen. Rat LD50 (inhalation) 64000 ppm/4H

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Section III. Hazards Identification
Acute Health Effects Toxic if ingested or inhaled. Avoid prolonged contact with this material. Overexposure may result in serious illness or death.
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Neoplastic by RTECS criteria
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Tumorigenic Effects:
Mouse TDLo (Subcutaneous) 9240 mg/kg/77 weeks intermittent
Toxic Effects:
Tumorigenic- Neoplastic by RTECS criteria
Tumorigenic- Tumors at site of application.
DEVELOPMENTAL TOXICITY: Reproductive Effects:
Rat TCLo (Inhalation) 20000 pm/7 hours. Female 1-22 days of pregnancy.
Toxic Effects:
Specific Developmental Abnormalities- Musculoskeletal system
Specific Developmental Abnormalities- Cardiovascular (circulatory) system
Specific Developmental Abnormalities- Urogenital system
Rat TDLo (Oral) 35295 mg/kg. Female 1-15 days of pregnancy
Toxic Effects:
Effects on Fertility- Female fertility index
Effects on Fertility- Pre-implantation mortality
Effects on Fertility- Post-implantation mortality
Mouse TDLo (Oral) 4gm/kg. Female 7 days of pregnancy
Toxic Effects:
Specific Developmental Abnormalities- Craniofacial (including nose and tongue)
Specific Developmental Abnormalities- Musculoskeletal system
Repeated exposure to an highly toxic material may produce general deterioration of health by an accumulation in one or
many human organs.

---

Section IV. First Aid Measures
Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
Eye Contact
minutes. Get medical attention.
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing
Skin Contact
and shoes. Wash clothing before reuse. Thoroughly clean shoes before reuse. Get medical attention immediately.
Inhalation If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
Continued on Next Page
cis-1,3-Dichloropropene
(1mg/ml in Methanol) [for Water Analysis]
INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Ingestion
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
464°C (867.2°F) (Methanol)
Flammable. Auto-Ignition
Flammability
Flash Points Flammable Limits LOWER: 5.5% UPPER: 44% (Methanol)
23.9°C (75°F).
12°C (53.6°F). (Methanol)
Combustion Products These products are toxic carbon oxides (CO, CO2), halogenated compounds
WARNING: Highly toxic HCl gas is produced during combustion.
Fire Hazards
Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
Flammable liquid.
SMALL FIRE: Use DRY chemical powder.
and Instructions
LARGE FIRE: Use alcohol foam, water spray or fog. Cool containing vessels with water jet in order to prevent pressure
build-up, autoignition or explosion. Consult with local fire authorities before attempting large scale fire-fighting operations.

---

Section VI. Accidental Release Measures
Spill Cleanup Flammable material. Toxic material. Environmentally hazardous material. Irritating material. Heat sensitive material.
Hygroscopic material.
Instructions
Keep away from heat. Mechanical exhaust required. Stop leak if without risk. Absorb with DRY earth, sand or other
non-combustible material. DO NOT get water inside container. DO NOT touch spilled material. Use water spray to reduce
vapors. Prevent entry into sewers, basements or confined areas; dike if needed. Consult federal, state, and/or local
authorities for assistance on disposal.

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Section VII. Handling and Storage
Handling and Storage FLAMMABLE. TOXIC. ENVIRONMENTAL HAZARD. IRRITANT. HEAT SENSITIVE. HYGROSCOPIC. FREEZE. Keep
locked up.. Keep away from heat. Mechanical exhaust required. Avoid excessive heat and light. DO NOT ingest. Do not
Information
breathe gas/fumes/ vapor/spray. Wear suitable protective clothing. If ingested, seek medical advice immediately and show
the container or the label. Treat symptomatically and supportively.
Always store away from incompatible compounds such as oxidizing agents.

---

Section VIII. Exposure Controls/Personal Protection
Engineering Controls Provide exhaust ventilation or other engineering controls to keep the airborne concentrations of vapors below their respective
threshold limit value. Ensure that eyewash station and safety shower is proximal to the work-station location.
Personal Protection Splash goggles. Lab coat. Vapor respirator. Boots. Gloves. A MSHA/NIOSH approved respirator must be used to avoid
inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling this
product.
Exposure Limits This chemical is classified as a possible carcinogen. There is no acceptable exposure limit for a carcinogen.

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Section IX. Physical and Chemical Properties
Liquid. (Clear. Colorless, amber.) Solubility
Physical state @ 20°C Soluble in ether, benzene, chloroform,
water.
1.224 (water=1) Miscible with hydrocarbons, halgenated
Specific Gravity
0.79 (Methanol) solvents, esters, and ketones.
Molecular Weight 110.97 Partition Coefficient The product is more soluble in oil;
32.04 (Methanol) log(oil/water) = 2.1
Boiling Point 104.3°C (219.7°F) Vapor Pressure 3.5 kPa (@ 20°C)
64°C (147.2°F) (Methanol) 97.68 mmHg (@ 20°C) (Methanol)
Melting Point -98°C (-144.4°F) (Methanol) Vapor Density 1.4 (Air = 1)
1.1 (Air = 1) (Methanol)
Not available. Not available.
Refractive Index Volatility
Critical Temperature Not available. Odor Chloroform like, sharp, sweet, penetrating,
irritating odor.
Not available. Not available.
Viscosity Taste
Continued on Next Page
cis-1,3-Dichloropropene
(1mg/ml in Methanol) [for Water Analysis]

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Section X. Stability and Reactivity Data

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Stability
Conditions of Instability Avoid excessive heat and light.
Incompatibilities
Reactive with oxidizing agents, reducing agents, acids, acid chlorieds, acid anhydrides, and alkali metals.

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Section XI. Toxicological Information
UC8325000
RTECS Number
Routes of Exposure Eye Contact. Ingestion. Inhalation.
(Methanol)
Toxicity Data
Rat LD50 (oral) 5600 mg/kg
Rabbit LD50 (dermal) 15800 mg/kg
Rat LD50 (inhalation) 64000 ppm/4H
Chronic Toxic Effects CARCINOGENIC EFFECTS : Neoplastic by RTECS criteria
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Tumorigenic Effects:
Mouse TDLo (Subcutaneous) 9240 mg/kg/77 weeks intermittent
Toxic Effects:
Tumorigenic- Neoplastic by RTECS criteria
Tumorigenic- Tumors at site of application.
DEVELOPMENTAL TOXICITY: Reproductive Effects:
Rat TCLo (Inhalation) 20000 pm/7 hours. Female 1-22 days of pregnancy.
Toxic Effects:
Specific Developmental Abnormalities- Musculoskeletal system
Specific Developmental Abnormalities- Cardiovascular (circulatory) system
Specific Developmental Abnormalities- Urogenital system
Rat TDLo (Oral) 35295 mg/kg. Female 1-15 days of pregnancy
Toxic Effects:
Effects on Fertility- Female fertility index
Effects on Fertility- Pre-implantation mortality
Effects on Fertility- Post-implantation mortality
Mouse TDLo (Oral) 4gm/kg. Female 7 days of pregnancy
Toxic Effects:
Specific Developmental Abnormalities- Craniofacial (including nose and tongue)
Specific Developmental Abnormalities- Musculoskeletal system
Repeated exposure to an highly toxic material may produce general deterioration of health by an accumulation in one or many
human organs.
Toxic if ingested or inhaled. Avoid prolonged contact with this material. Overexposure may result in serious illness or death.
Acute Toxic Effects
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the eye
is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.

---

Section XII. Ecological Information
Not available.
Ecotoxicity
Environmental Fate cis-1,3-Dichloropropene's production and use as a soil fumigant and nematicide is expected to result in its direct release to
the environment. If released to air, a vapor pressure of 26 mm Hg at 20 deg C indicates cis-1,3-dichloropropene will exist
solely as a vapor in the ambient atmosphere. Vapor-phase cis-1,3-dichloropropene will be degraded in the atmosphere by
reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 46 hrs. If
released to soil, cis-1,3-dichloropropene is expected to have very high mobility based upon a range of Kocs from 20 to 42.
Volatilization from moist soil surfaces is expected to be an important fate process based upon a Henry's Law constant of
2.7X10-3 atm-cu m/mole. cis-1,3-Dichloropropene may volatilize from dry soil surfaces based upon its vapor pressure.
cis-1,3-Dichloropropene is expected to biodegrade in soil and water under aerobic and anaerobic conditions. Under aerobic
conditions, the half-life for 1,3-dichloropropene was 12 days in a loam soil. Under anaerobic conditions at 25 deg C, in both a
silty clay loam and sandy loam soil, the half-life was 2.4 days. If released into water, cis-1,3-dichloropropene is not expected
to adsorb to suspended solids and sediment based upon the Kocs. Volatilization from water surfaces is expected to be an
important fate process based upon this compound's Henry's Law constant. Estimated volatilization half-lives for a model river
and model lake are 1.3 and 102 hrs, respectively. An estimated BCF of 8 suggests the potential for bioconcentration in
aquatic organisms is low. cis-1,3-Dichloropropene degrades by chemical hydrolysis; at pH values of 5, 7, 9, the half-life of
1,3-dichloropropene was 13.5 days at 20 deg C. Occupational exposure to cis-1,3-dichloropropene may occur through
inhalation and dermal contact with this compound at workplaces where cis-1,3-dichloropropene is produced or used.
Occupational exposure may also occur for agricultural workers using this compound as a soil fumigant and nematicide. The
general population may be exposed to cis-1,3-dichloropropene via inhalation of ambient air and drinking water in areas where
cis-1,3-dichloropropene is used a soil fumigant and nematicide.
(Methanol)
Methanol's production and use as a solvent, fuel additive, and in the production of formaldehyde, acetic acid, and methyl
tertiary butyl ether (MTBE) may result in its release to the environment through various waste streams. Methanol has been
identified as a natural emission product from various plants and as a biological decomposition product of biological wastes
and sewage. If released to the atmosphere, a vapor pressure of 127 mm Hg at 25 deg C indicates that methanol will exist
solely in the vapor phase. Vapor phase methanol is degraded in the atmosphere by reaction with photochemically-produced
hydroxyl radicals; the half-life for this reaction in air is estimated to be 17 days. If released to soil, methanol is expected to
have very high mobility based upon an estimated Koc of 1. Volatilization from moist soil surfaces is expected to be an
important fate process based upon a Henry's Law constant of 4.55X10-6 atm-cu m/mole. Methanol may also volatilize from
dry soils based upon it vapor pressure. Biodegradation of methanol in soils is expected to occur rapidly based on half-lives in
a sandy silt loam from Texas and a sandy loam from Mississippi of 1 and 3.2 days, respectively. If released into water,
methanol is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from
water surfaces is expected to be an important fate process based upon this compound's Henry's Law constant. Estimated
volatilization half-lives for a model river and model lake are 3 and 35 days, respectively. Biodegradation is expected to occur
Continued on Next Page
cis-1,3-Dichloropropene
(1mg/ml in Methanol) [for Water Analysis]
in natural waters since methanol is degraded quickly in soils and was biodegraded rapidly in various aqueous screening tests
using sewage seed or activated sludge. BCF values of less than 10, measured in fish suggests bioconcentration in aquatic
organisms is low. Hydrolysis of methanol and photolysis in sunlit surface waters are not expected since methanol lacks
functional groups that are susceptible to hydrolysis or photolysis under environmental conditions. Occupational exposure to
methanol may occur through inhalation and dermal contact with this compound at workplaces where methanol is produced or
used. Monitoring data indicate that the general population may be exposed to methanol via inhalation of ambient air, and
ingestion of food and drinking water.

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Section XIII. Disposal Considerations
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
Waste Disposal
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
DOT Classification DOT CLASS 3: Flammable liquid.
DOT CLASS 6.1: Toxic material.
PIN Number
Proper Shipping Name Flammable liquid, toxic, n.o.s.
II
Packing Group (PG)
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification CLASS B-2: Flammable liquid with a flash point lower than 37.8°C (100°F).
CLASS D-1B: Material causing immediate and serious toxic effects (TOXIC).
(Canada)
EINECS Number (EEC) 233-195-8
200-659-6 (Methanol)
EEC Risk Statements R10- Flammable.
R18- In use, may form flammable/explosive vapor-air mixture.
R23/24/25- Toxic by inhalation, in contact with skin and if swallowed.
R51- Toxic to aquatic organisms.
R53- May cause long-term adverse effects in the aquatic environment.
R36/37/38- Irritating to eyes, respiratory system and skin.
R45- May cause cancer.
Japanese Regulatory Data ENCS no.: 2-125

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

顺式-1,3-二氯丙烯是一种重要的化工原料，主要用于有机合成，如制备氯代烃、酯类、醚类和其他有机化合物。

用途

顺式-1,3-二氯丙烯属于易燃液体类别。其爆炸物危险特性在于与空气混合可爆。此外，该物质在明火、受热或接触氧化剂的情况下也可燃烧，并释放有毒的氯化物和刺激性的烟雾。

储运特性

储存时应将物品置于通风良好且低温干燥的地方，并轻装轻卸。存储过程中需要避免与氧化剂和酸类分开存放以确保安全。

灭火方法

遇到火灾，可以使用雾状水、泡沫或二氧化碳灭火器以及1211灭火剂进行扑救。

反应信息

• 作为反应物：
  描述：

  顺式-1,3-二氯丙烯 在 sodium carbonate 作用下， 以 水 为溶剂， 以91%的产率得到1-chloropropenol
  参考文献：
  名称：

  一种1,3-丙烯磺酸内酯的合成方法

  摘要：

  本发明公开了一种1,3‑丙烯磺酸内酯的合成方法，包括如下步骤：1、1‑氯丙烯醇的合成；2、丙炔醇的合成；3、3‑羟基丙烯磺酸的合成；4、1,3‑丙烯磺酸内酯的合成。该方法合成路线简单，原料便宜易得，合成成本低，而且收率高。

  公开号：

  CN107556286A
• 作为产物：
  描述：

  3-氯丙烯 在 氯 作用下， 生成 顺式-1,3-二氯丙烯 、 反式-1,3-二氯-1-丙烯
  参考文献：
  名称：

  The High Temperature Chlorination of Various Mono- and Dichloropropenes

  摘要：

  DOI：

  10.1021/ja01102a037

文献信息

• Direct, Mild, and General <i>n</i>-Bu₄NBr-Catalyzed Aldehyde Allylsilylation with Allyl Chlorides
  作者：Makeda A. Tekle-Smith、Kevin S. Williamson、Isaac F. Hughes、James L. Leighton

  DOI：10.1021/acs.orglett.7b03193

  日期：2017.11.3

  A direct, mild, and general method for the enantioselective allylsilylation of aldehydes with allyl chlorides is reported. The reactions are effectively catalyzed by 5 mol % of n-Bu4NBr, and this rate acceleration allows the use of complex allyl donors in fragment-coupling reactions and of electron-deficient allyl donors. The results are (1) significant progress toward a “universal” asymmetric aldehyde

  报道了用烯丙基氯对醛进行对映选择性烯丙基甲硅烷化的直接，温和和通用的方法。该反应有效地由5 mol％的n -Bu 4 NBr催化，并且该速率加速允许在片段偶联反应中使用复杂的烯丙基供体和电子不足的烯丙基供体。结果是（1）朝着“通用”不对称醛烯丙基化反应的重大进展，该反应可以可靠且高度立体选择性地偶联任何烯丙基氯-醛组合，以及（2）发现了醛烯丙基甲硅烷基化反应的新型亲核催化剂。
• Novel Platensimycin Derivatives, Their Intermediates, and Process for Preparing the Same, and New Process for Preparing Platensimycin
  申请人：Lee Eun

  公开号：US20110028741A1

  公开（公告）日：2011-02-03

  The present invention relates to novel platensimycin derivatives, their intermediates and preparing methods of the same. Platensimycin is known as an effective antibiotic material having a broad antimicrobial spectrum and its derivatives are also expected to be effective antibiotic candidates. The present invention also relates to a novel preparing method of platensimycin. The intermediates used for the production of platensimycin and its derivatives of the present invention are tricyclo ketone derivatives and tetracyclo derivatives. Tetracyclo derivatives are prepared from tricyclo ketone derivatives prepared by carbonyl ylide [3+2] cycloaddition of dia-zoketone derivative.

  本发明涉及新型的platensimycin衍生物，它们的中间体以及相同的制备方法。已知Platensimycin是一种具有广泛抗菌谱的有效抗生素材料，其衍生物也被期望是有效的抗生素候选物。本发明还涉及一种新型的platensimycin制备方法。用于生产本发明的platensimycin及其衍生物的中间体是三环酮衍生物和四环衍生物。四环衍生物是由通过二氮杂酮衍生物的羰基亚烯[3+2]环加成反应制备的三环酮衍生物制备的。
• Pyrimidine derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0295839A3

  公开（公告）日：1991-07-31

  This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): and stereoisomers thereof, wherein R' is selected from alkyl; alkenyl; alkynyl: haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen;R2 is selected from alkyl; haloalkyl; alkoxy; alkylamino; dialkylamino; halogen; cycloalkyl optionally substituted by halogen or alkyl; and phenyl optionally substituted by alkyl, haloalkyl, halogen or alkoxy;R3 is selected from hydrogen and halogen;R4 is the residue of an alcohol of formula R4-OH which forms an insecticidal ester when combined with chrysanthemic acid, permethrin acid or cyhalothrin acid; andX is selected from oxygen and sulphur; provided that R2 may not represent an alpha-branched alkyl group or a cycloalkyl group when R' represents 1-methylethyl.

  这项发明提供了公式（I）的新型杀虫和杀螨活性嘧啶衍生物及其立体异构体，其中 R'从烷基；烯烃基；炔烃基；卤代烷基；卤代烯烃基；和环烷基中选择，可选择地被烷基或卤素取代；R2从烷基；卤代烷基；烷氧基；烷基氨基；二烷基氨基；卤素；可选择地被卤素或烷基取代的环烷基；和可选择地被烷基、卤代烷基、卤素或烷氧基取代的苯基中选择；R3从氢和卤素中选择；R4是公式R4-OH的醇残基，当与菊酯酸、氯氰菊酯酸或氟氯氰菊酯酸结合时形成杀虫酯；X从氧和硫中选择；但是当R'代表1-甲基乙基时，R2可能不代表α-支链烷基或环烷基。
• Rhodium-Catalyzed Cyclopropanation of Alkenes with Dimethyl Diazomalonate
  作者：Francisco González-Bobes、Michaël D. B. Fenster、Susanne Kiau、Laxma Kolla、Sergei Kolotuchin、Maxime Soumeillant

  DOI：10.1002/adsc.200800027

  日期：2008.4.7

  α′-tetramethyl-1,3-benzenedipropanoate] to catalyze the cyclopropanation of a wide range of alkenes with malonate-derived carbenoids under mild reaction conditions is reported in this communication. The experimental protocol is remarkably simple, uses readily accessible and stable dimethyl diazomalonate with very low catalyst loading. More importantly, the alkene is employed as a limiting reagent.

  α，α，α'，α'-四甲基-1,3-苯二丙酸酯[Rh 2（esp）2；据报道，esp =α，α，α'，α'-四甲基-1,3-苯二丙酸酯]在温和的反应条件下与丙二酸酯衍生的类胡萝卜素催化多种烯烃的环丙烷化反应。实验方案非常简单，使用容易获得且稳定的重氮丙二酸二甲酯，催化剂的负载量非常低。更重要的是，烯烃被用作限制试剂。
• Insecticidally and acaricidally active pyrimidine esters and
  申请人：Imperial Chemical Industries PLC

  公开号：US04962109A1

  公开（公告）日：1990-10-09

  This invention provides novel insecticidally and acaricidally active pyrimidine derivatives of formula (I): ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl; alkenyl; alkynyl; haloalkyl; haloalkenyl; and cycloalkyl optionally substituted by alkyl or halogen; R.sup.2 is selected from alkyl; haloalkyl; alkoxy; alkylamino; dialkylamino; halogen; cycloalkyl optionally substituted by halogen or alkyl; and phenyl optionally substituted by alkyl, haloalkyl, halogen or alkoxy; R.sup.3 is selected from hydrogen and halogen; R.sup.4 is the residue of an alcohol of formula R.sup.4 --OH which forms an insecticidal ester when combined with chrysanthemic acid, permethrin acid or cyhalothrin acid; and X is selected from oxygen and sulphur.

  这项发明提供了公式（I）的新型杀虫和杀螨活性嘧啶衍生物：##STR1##及其立体异构体，其中R.sup.1选自烷基；烯基；炔基；卤代烷基；卤代烯基；和环烷基，可选择地被烷基或卤素取代；R.sup.2选自烷基；卤代烷基；烷氧基；烷基氨基；二烷基氨基；卤素；环烷基，可选择地被卤素或烷基取代；和苯基，可选择地被烷基，卤代烷基，卤素或烷氧基取代；R.sup.3选自氢和卤素；R.sup.4是公式R.sup.4 --OH的醇残基，当与菊酯酸，氯氰菊酯酸或氰戊菊酯酸结合时形成杀虫酯；X选自氧和硫。

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