三氯苯 - CAS号 87-61-6

物化性质

熔点：

51-53 °C (lit.)
沸点：

218-219 °C (lit.)
密度：

1,69 g/cm3
蒸气密度：

6.25 (vs air)
闪点：

260 °F
溶解度：

0.02克/升
LogP：

4.139 at 25℃
物理描述：

1,2,3-trichlorobenzene appears as a white solid with a sharp chlorobenzene odor. Insoluble in water and denser than water. Hence sinks in water. Melting point 63-64°C (145-147°F).
颜色/状态：

Colorless liquid
蒸汽密度：

6.2 (NTP, 1992) (Relative to Air)
蒸汽压力：

0.21 mm Hg at 25 °C
亨利常数：

0.00 atm-m3/mole
分解：

When heated to decomp, it emits toxic fumes of /hydrogen chloride/. /2,3,6-trichlorobenzoic acid/
粘度：

1.68 mPa.s at 50 °C
汽化热：

291 J/g at 100 °C; 271.7 J/g at 150 °C; 251.6 J/g at 200 °C
气味阈值：

3 ppm
保留指数：

1183;1190;1199;1204;1214;1224.6;1211;1228;1211;1217;1228;1189;1211;1225.9;1194.2;1211.5;1197;1194;1176;1182;1179.8;1195.7;1188

计算性质

辛醇/水分配系数(LogP)：

4.1
重原子数：

9
可旋转键数：

0
环数：

1.0
sp3杂化的碳原子比例：

0.0
拓扑面积：

0
氢给体数：

0
氢受体数：

0

ADMET

代谢

1,2,3-三氯苯在兔体内被代谢成N-乙酰-S-(2,3,4-三氯苯基)-L-半胱氨酸、2,3,4-三氯酚和3,4,5-三氯酚。/来自表格/

1,2,3-trichlorobenzene is metabolized to n-acetyl-s-(2,3,4-trichlorophenyl)-l-cysteine, 2,3,4-trichlorophenol, & 3,4,5-trichlorophenol in rabbits. /from table/

来源:Hazardous Substances Data Bank (HSDB)

代谢

在使用三种异构体的三氯苯对家兔进行代谢研究时，每只家兔给药0.5克/千克，1,2,3-三氯苯是最快被代谢的……在5天内，62%……发生了葡萄糖醛酸结合。主要代谢物是2,3,4-三氯酚；少量的3,4,5-三氯酚、3,4,5-三氯儿茶酚和巯基尿酸也被……检测到。

In metabolic studies with rabbits using each of the 3 isomeric trichlorobenzenes at 0.5 g/kg, 1,2,3-trichlorobenzene was the one most rapidly metabolized ... in 5 days, 62% ... underwent glucuronic conjugation. The major metabolite was 2,3,4-trichlorophenol; small amt of 3,4,5-trichlorophenol, 3,4,5-trichlorocatechol, & mercapturic acid were ... detected.

来源:Hazardous Substances Data Bank (HSDB)

代谢

三氯苯通过口服、吸入和皮肤途径被吸收。它被认为通过细胞色素P-450酶代谢为包括酚、巯基尿酸和儿茶酚等代谢物。

Trichlorobenzene is absorbed via oral, inhalation, and dermal routes. It is believed to be metabolized via cytochrome p-450 enzymes into metabolites that include phenols, mercapturic acid, and catechols.(T38)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

毒性总结

三氯苯可能会解除线粒体的氧化磷酸化偶联，诱导钾离子释放并抑制呼吸控制。其代谢物可能会与细胞蛋白共价结合并烷基化DNA。

Trichlorobenzene may uncouple mitochondrial oxidative phosphorylation, inducing potassium ion release and inhibiting respiratory control. It's metabolites may covalently bind to cellular proteins and alkylate DNA. (A154, A155)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

健康影响

高浓度的三氯苯可能会损害肝脏、肾脏和甲状腺。

High levels of trichlorobenzene may damage the liver, kidney, and thyroid. (A153)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

暴露途径

该物质可以通过吸入其气溶胶和通过吞食被吸收进人体。

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

暴露途径

口服 (T38)；吸入 (T38)；皮肤给药 (T38)

Oral (T38) ; inhalation (T38) ; dermal (T38)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

兔子口服1,2,3-三氯苯五天后，78%的给药量以单体酚的形式被排出。

... Five days after the oral administration of 1,2,3-trichlorobenzene to rabbits, 78% ... of the administered dose was excreted as monophenols.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

三氯苯的所有三种同分异构体都被胃肠道、完整皮肤和肺吸收了。

All three isomers of trichlorobenzene were absorbed from the gastrointestinal tract, intact skin, and lung.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

研究了1,2,3-三氯苯、1,2,4-三氯苯和1,3,5-三氯苯在雄性Sprague Dawley大鼠体内的组织分布和消除。禁食动物通过灌胃给予单剂量的10 mg/kg的(14)C标记的异构体。在给药后0.5、1、24小时以及1、2、7、14、28和56天进行系列牺牲。放射性测定利用了肝脏、肾脏、脾脏、大脑、胰腺、肺、心脏、大腿肌肉、皮肤、肾周脂肪、睾丸、膀胱、肾上腺、附睾、精囊、前列腺、胃肠道、血液和唾液腺。每个组织的数据被拟合到线性隔室药代动力学模型。测定了1,2,3-三氯苯和1,3,5-三氯苯异构体在尿和粪便中排出的(14)C的量。标记的异构体在给药后30分钟内在血液和组织中出现放射性，大约在4小时达到峰值，并缓慢下降到背景水平。与1,2,4-三氯苯相关的放射性在28天后降至背景水平。膀胱、肾脏、脂肪、皮肤、肝脏和肾上腺在治疗后24小时内显示出较高的1,2,4-三氯苯活性。由于1,2,3-三氯苯的放射性，肝脏、脂肪和皮肤在56天后降至背景水平，其他组织在28天后降至背景水平。1,2,3-三氯苯的最高浓度出现在肝脏、脂肪、肾脏和膀胱中。1,3,5-三氯苯的放射性在所有检查的组织中在56天后仍然保持显著水平。大约85%的1,3,5-三氯苯和92%的1,2,3-三氯苯在给药后24小时内被排出。隔室分析显示1,3,5-三氯苯具有最高的指数衰减线性系数值。

The tissue distribution and elimination of 1,2,3-trichlorobenzene, 1,2,4-trichlorobenzene, and 1,3,5-trichlorobenzene were examined in male Sprague Dawley rats. Fasted animals were given single doses of 10 mg/kg of the (14)C labeled isomers by gavage. Serial sacrifices were performed at 0.5, 1, and 24 hr and 1, 2, 7, 14, 28, and 56 days post administration. Radioassays utilized the liver, kidneys, spleen, brain, pancreas, lung, heart, thigh muscle, skin, perirenal fat, testes, bladder, adrenals, epididymis, seminal vesicles, prostate, gastrointestinal tract, blood, and salivary glands. The data for each tissue was fitted to a linear compartmental pharmacokinetic model. The amount of (14)C excreted in urine and feces was determined daily for 1,2,3-trichlorobenzene and 1,3,5-trichlorobenzene isomers. Radioactivity from the labeled isomers appeared in the blood and tissues within 30 min of administration, peaked at approximately 4 hr, and slowly declined to background levels. Radioactivity attributed to 1,2,4-trichlorobenzene dropped to background levels after 28 days. The bladder, kidney, fat, skin, liver, and adrenals showed high 1,2,4-trichlorobenzene activity up to 24 hr post treatment. Radioactivity due to 1,2,3-trichlorobenzene dropped to background levels after 56 days for liver, fat, and skin and 28 days for the other tissues. The highest 1,2,3-trichlorobenzene concentrations were found in liver, fat, kidney, and bladder. Significant levels of radioactivity from 1,3,5-trichlorobenzene remained in the tissues after 56 days for all tissues examined. Approx 85% of 1,3,5-trichlorobenzene and 92% of the 1,2,3-trichlorobenzene were excreted within 24 hr of dosing. Compartmental analysis showed 1,3,5-trichlorobenzene to have the highest values for the linear coefficients of exponential decay.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

TSCA：

Yes
危险等级：

9
危险品标志：

Xn
安全说明：

S26,S36,S36/37,S45,S61
危险类别码：

R22,R38
WGK Germany：

3
海关编码：

29036990
危险品运输编号：

UN 3077 9/PG 3
危险类别：

9
RTECS号：

DC2095000
包装等级：

III

SDS

SDS：a6be3d3ce7aff439cd09c7a6912e3bad

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制备方法与用途

用途

1,2,3-三氯苯是一种无色液体或板状结晶（在酒精中），可用作医药、染料、农药原料及中间体，主要用于制取均苯四甲酸二酐，并用于生产聚酰亚胺树脂、染料、增塑剂、表面活性剂等。

合成

1,2,3-三氯苯的合成方法如下：在500毫升四口瓶中加入低油260克，开启蓝色荧光灯，将料液加热至约160℃，开始通入氯气进行反应，控制氯气流量为5.0升/小时，并保持氯化温度在180℃。反应完毕后通过碱洗和水洗分层得到油层，再取样溶解于甲苯中进行分析。

化学性质

板状结晶（在酒精中）。不溶于水，微溶于乙醇，易溶于乙醚。

用途

1,2,3-三氯苯主要用于有机合成。具体应用包括制备均苯四甲酸二酐、生产聚酰亚胺树脂、染料、增塑剂和表面活性剂等。

生产方法

热解法：干燥的六六六无毒体在热解釜中加热后即可获得三氯苯，同时副产大量氯化氢。
碱解法：将六六六无毒体与石灰乳共热可得三氯苯，并伴有大量氯化钙液生成。所得三氯苯为1,2,4-三氯苯、1,3,5-三氯苯及1,2,3-三氯苯的混合物，其中以1,2,4-三氯苯为主要组分。采用石灰乳法生产时，1,2,4-三氯苯含量通常超过75%，而1,2,3-三氯苯约占总量的20%。

类别

农药

毒性分级

中毒

急性毒性

口服 - 大鼠 LD50: 1830 毫克/公斤
腹腔 - 小鼠 LD50: 1390 毫克/公斤

可燃性危险特性

明火可燃；燃烧释放有毒氯化物烟雾；水解生成盐酸。

储运特性

库房通风、低温干燥存储；与食品添加剂分开存放。

灭火剂

使用雾状水、泡沫、二氧化碳或砂土灭火。

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
1,2,3,5-四氯苯	1,2,3,5-tetrachlorobenzene	634-90-2	C₆H₂Cl₄	215.894
1,2,3,4-四氯苯	1,2,3,4,-tetrachlorobenzene	634-66-2	C₆H₂Cl₄	215.894
六氯苯	hexachlorobenzene	118-74-1	C₆Cl₆	284.784
五氯苯	pentachlorobenzene	608-93-5	C₆HCl₅	250.339
1,2,4,5-四氯苯	1,2,4,5-tetrachlorobenzene	95-94-3	C₆H₂Cl₄	215.894
三氯苯	1,2,4-Trichlorobenzene	120-82-1	C₆H₃Cl₃	181.449
邻二氯苯	1,2-dichloro-benzene	95-50-1	C₆H₄Cl₂	147.004
1,3-二氯苯	1,3-Dichlorobenzene	541-73-1	C₆H₄Cl₂	147.004
1,3,5-三氯苯	1,3,5-trichlorobenzene	108-70-3	C₆H₃Cl₃	181.449
3,4,5-三氯苯胺	3,4,5-trichloroaniline	634-91-3	C₆H₄Cl₃N	196.463

下游产品

中文名称	英文名称	CAS号	化学式	分子量
1,2,3,4-四氯苯	1,2,3,4,-tetrachlorobenzene	634-66-2	C₆H₂Cl₄	215.894
六氯苯	hexachlorobenzene	118-74-1	C₆Cl₆	284.784
三氯苯	1,2,4-Trichlorobenzene	120-82-1	C₆H₃Cl₃	181.449
邻二氯苯	1,2-dichloro-benzene	95-50-1	C₆H₄Cl₂	147.004
1,3-二氯苯	1,3-Dichlorobenzene	541-73-1	C₆H₄Cl₂	147.004
1,3,5-三氯苯	1,3,5-trichlorobenzene	108-70-3	C₆H₃Cl₃	181.449
3,4,5-三氯溴苯	5-bromo-1,2,3-trichlorobenzene	21928-51-8	C₆H₂BrCl₃	260.345
3,4,5-三氯苯酚	3,4,5-trichlorophenol	609-19-8	C₆H₃Cl₃O	197.448

反应信息

作为反应物：

描述：

三氯苯在 palladium 10% on activated carbon 、氢气、 sodium hydroxide 作用下，以正己烷、水为溶剂， 20.0 ℃ 、101.33 kPa 条件下，生成邻二氯苯

参考文献：

名称：

Kinetic study of the hydrogenolysis of polychlorobenzenes over a Pd/C catalyst in an alkaline aqueous-n-hexane system

摘要：

The kinetics of the hydrogenolysis of chlorobenzene, dichlorobenzenes and some trichlorobenzenes over a 10% Pd/C catalyst was studied using a multiphase system. The reactions were carried out in a batch reactor with an aqueous NaOH/n-hexane solution of chloroaromatic compound as the liquid phase. Benzene was the final product of the hydrogenolysis of all the compounds studied. Hydrogenolysis was more effective in the presence of in situ generated hydrogen than gaseous hydrogen. The initial reaction rates and TOFs of dichlorobenzenes and trichlorobenzenes were slightly lower than those of chlorobenzene. The position of the chlorine atoms in trichlorobenzenes affects the kinetics of the removal of the first chlorine from these molecules. The differences in chlorine reactivity were explained by the inductive and steric effects induced by the benzene-CI bonds. (C) 2010 Elsevier B.V. All rights reserved.

DOI：

10.1016/j.catcom.2010.02.018
作为产物：

描述：

2,3-二氯硝基苯在苯基二氯化磷作用下，以 various solvent(s) 为溶剂，反应 5.0h，以93%的产率得到三氯苯

参考文献：

名称：

A simple direct procedure for the regiospecific preparation of chloro aromatic compounds

摘要：

DOI：

10.1021/jo00247a042
作为试剂：

描述：

苯亚甲基-2-氨基萘在二溴化二硫、 sulfur 、三氯苯作用下，生成 2-phenylnaphtho[2,1-d]thiazole

参考文献：

名称：

Preparation of thiazole compounds

摘要：

公开号：

US02028118A1

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文献信息

Proton Mobility in 2-Substituted 1,3-Dichlorobenzenes: “ortho” or “meta” Metalation?

作者：Manfred Schlosser、Christophe Heiss、Elena Marzi、Rosario Scopelliti

DOI：10.1002/ejoc.200600350

日期：2006.10

Nine 1,3-dichlorobenzene congeners were selected as model compds. to assess the relative rates of proton abstraction from 4- and 5-positions ("ortho" vs. "meta" metalation). Using lithium 2,2,6,6-tetramethylpiperidide as the basic reagent, the chlorine-adjacent 4-position underwent metalation exclusively. In contrast, attack at the chlorine-remote 5-position became significant even in the case of moderately

选择九个 1,3-二氯苯同系物作为模型化合物。评估从 4 位和 5 位（“邻位”与“元”金属化）提取质子的相对速率。使用 2,2,6,6-四甲基哌啶锂作为碱性试剂，4 位氯附近专门进行金属化。相比之下，当使用仲丁基锂时，即使在中等大小的 2-取代基（如二甲氨基或乙基）的情况下，对氯远程 5-位的攻击也变得显着。“邻位/对位”(4-/5-) 比率范围为 80:20 至 65:35。与碳取代基相反，硅更显着的“元取向”效应可归因于芳族的 pi 极化的不同。戒指。[在 SciFinder (R) 上]
TETRAZOLINONE COMPOUND AND USE OF SAME

申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

公开号：US20160081339A1

公开（公告）日：2016-03-24

A tetrazolinone compound of formula (1): wherein R 1 and R 2 each independently represents a hydrogen atom, etc.; R 3 represents a C1-C6 alkyl group, etc.; R 4 , R 5 , and R 6 each independently represents a hydrogen atom, etc.; A represents a C6-C16 aryl group optionally having one or more atoms or groups selected from Group P, etc.; Q represents the following group Q1, etc.; and X represents an oxygen atom or a sulfur atom, has excellent control activity against pests.

一种化学式（1）所示的四唑酮化合物：其中R1和R2分别独立表示氢原子，等等； R3表示C1-C6烷基，等等；R4、R5和R6分别独立表示氢原子，等等；A表示一个C6-C16芳基，可选地具有来自P族等组的一个或多个原子或基团；Q表示以下Q1组等；以及 X表示氧原子或硫原子，对害虫具有出色的控制活性。
[EN] ELECTROLUMINESCENT DEVICE<br/>[FR] DISPOSITIF ELECTROLUMINESCENT

申请人：CIBA SC HOLDING AG

公开号：WO2003105538A1

公开（公告）日：2003-12-18

Disclosed are electroluminescent devices that comprise organic layers that contain certain 2H-benzotriazole compounds. The 2H-benzotriazole compounds of blue-emitting, durable, organo-electrouminescent layers. The electroluminescent devices may be employed for full color display panels in for example mobile phones, televisions and personal computer screens.

揭示了包含特定2H-苯并三唑化合物的有机层的电致发光器件。这些2H-苯并三唑化合物用于蓝光发射、耐久的有机电致发光层。这些电致发光器件可用于移动电话、电视和个人电脑屏幕等全彩显示面板。
The reactions of unactivated aryl halides with sodium methoxide in HMPA

作者：L. Testaferri、M. Tiecco、M. Tingoli、D. Chianelli、M. Montanucci

DOI：10.1016/s0040-4020(01)97647-1

日期：——

Sodium methoxide reacts with dichlorobenzenes in HMPA to give the chloroanisoles as a result of a SNAr process. Excess MeONa then effects the demethylation of the ethers to give the chlorophenols via an SN2 reaction. With tri- and tetrachlorobenzenes the initially formed chloroanisoles can be dealkylated to chlorophenols or can suffer further substitution to give the chlorodimethoxybenzenes; these

由于S N Ar过程，甲醇钠与HMPA中的二氯苯反应生成氯茴香醚。然后过量的MeONa通过S N 2反应使醚脱甲基，得到氯酚。用三氯苯和四氯苯可以将最初形成的氯茴香醚脱烷基化为氯酚，或者可以进一步取代生成氯二甲氧基苯；它们与过量的MeONa反应，得到氯甲氧基苯酚。在取代基的电子效应的基础上，介绍并讨论了用二，三和四氯苯的各种异构体获得的结果。
[EN] METHODS FOR PRODUCING ARYLSULFUR PENTAFLUORIDES<br/>[FR] PROCÉDÉS DE PRODUCTION DE PENTAFLUORURES DE SOUFRE ARYLÉS

申请人：IM & T RES INC

公开号：WO2010014665A1

公开（公告）日：2010-02-04

Novel methods for preparing arylsulfur pentafluorides are disclosed. Arylsulfur halotetrafluoride is reacted with a fluoride source under hydrous conditions to form an arylsulfur pentafluoride. The purification method is also disclosed.

揭示了制备芳基硫五氟化物的新方法。芳基硫卤四氟化物在湿润条件下与氟化物源反应，形成芳基硫五氟化物。还公开了纯化方法。