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硝基氯苯 | 88-73-3

中文名称
硝基氯苯
中文别名
邻硝基氯苯;邻氯硝基苯;邻硝基氯化苯;邻硝基氯苯,邻硝;2-硝基氯苯;2-氯硝基苯;2-硝基氯化苯;1-氯-2-硝基苯;邻硝基氯代苯
英文名称
2-Chloronitrobenzene
英文别名
2-chloro-1-nitrobenzene;1-chloro-2-nitrobenzene;o-chloronitrobenzene;o-nitrochlorobenzene;2-nitrochlorobenzene;ortho-chloronitrobenzene
硝基氯苯化学式
CAS
88-73-3;25167-93-5
化学式
C6H4ClNO2
mdl
MFCD00007061
分子量
157.556
InChiKey
BFCFYVKQTRLZHA-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    241.15°C (rough estimate)
  • 密度:
    1.3768 (rough estimate)
  • 物理描述:
    O-nitrochlorobenzene appears as yellow crystals with an aromatic odor. Sinks in water. (USCG, 1999)
  • 颜色/状态:
    Yellow crystals
  • 熔点:
    32.5 °C
  • 闪点:
    127 °C
  • 溶解度:
    In water, 441 mg/L at 25 °C
  • 蒸汽密度:
    5.44 (NTP, 1992) (Relative to Air)
  • 蒸汽压力:
    0.018 mm Hg at 25 °C
  • 亨利常数:
    9.30e-06 atm-m3/mole
  • 自燃温度:
    470 °C
  • 粘度:
    2.09X10-3 Pa-s at 317.65 deg K
  • 汽化热:
    6.59X10+7 J/kmol at 306.14 deg K
  • 表面张力:
    4.37X10-2 N/m at 317.65 deg K
  • 保留指数:
    1193;1195;1221.4;1199

计算性质

  • 辛醇/水分配系数(LogP):
    2.2
  • 重原子数:
    10
  • 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:
    45.8
  • 氢给体数:
    0
  • 氢受体数:
    2

ADMET

代谢
Yields N-acetyl-S-(o-nitrophenyl)-L-cysteine, o-chloroaniline, 2-chloro-3-nitrophenol, 3-chloro-2-nitrophenol, 3-chloro-4-nitrophenol, 4-chloro-3-nitrophenol in rabbit... . /from table/
来源:Hazardous Substances Data Bank (HSDB)
代谢
氯硝基苯异构体的代谢在雄性Fischer-344大鼠的孤立肝细胞和肝亚细胞组分中进行比较。2-氯硝基苯通过孤立肝细胞转化为2-氯苯胺、2-氯苯胺-N-葡萄糖苷酸和S-(2-硝基苯基)谷胱甘肽,转化量大致相等(90分钟内添加底物的13-19%)。...使用肝微粒体的研究表明,将氯硝基苯还原为氯苯胺的过程受到SKF 525-A、美托拉宗一氧化碳的抑制,这表明细胞色素P-450在此反应中发挥作用。
The metabolism of radiolabeled monochloronitrobenzene isomers was compared in isolated hepatocytes and hepatic subcellular fractions from male Fischer-344 rats. 2-Chloronitrobenezene was converted by isolated hepatocytes to 2-chloroaniline, 2-chloroaniline-N-glucuronide, and S-(2-nitrophenyl)glutathione in approximately equal quantities (13-19% of the added substrate in 90 min). ... Studies with hepatic microsomes showed that reduction of the chloronitrobenzenes to chloroanilines was inhibited by SKF 525-A, metyrapone, and carbon monoxide, suggesting that cytochrome P-450 played a role in the reaction.
来源:Hazardous Substances Data Bank (HSDB)
代谢
1--2-硝基苯在体内的主要代谢途径包括将硝基还原为基,以及对苯环进行羟基化。除了形成2-氯苯胺外,还会生成相应的硝基,它们以葡萄糖醛酸和硫酸的共轭物形式被排出体外。2-氯苯胺也以未结合形式出现在尿液和粪便中。在将硝基还原为基的过程中,会形成高度反应性的羟基胺中间体,这种中间体在大鼠体内以及体外实验中均有检测到。
The main metabolic routes for 1-chloro-2-nitrobenzene in the body consist in reduction of the nitro group to an amino group and hydroxylation of the benzene ring. Apart from 2-chloroaniline, the corresponding nitrophenols and aminophenols are formed, which are excreted as conjugates of glucuronic acid and sulfuric acid. 2-chloroaniline also appears in the urine and feces in the unconjugated form. During reduction of the nitro group to the amino group, the hydroxylamine compound is formed as a highly reactive intermediate which has been detected both in vivo in rats, and in vitro.
来源:Hazardous Substances Data Bank (HSDB)
代谢
体外代谢:将标记有放射性碳-14(14C)的邻氯硝基苯与分离的大鼠肝细胞一起孵化。90分钟后,71%的邻氯硝基苯已被代谢;邻氯硝基苯的主要代谢途径是还原为邻氯苯胺(占总放射活性的19.2%);邻氯硝基苯还与谷胱甘肽结合;另外两种非常极性的代谢物,占总14C的14.2%,尚未被鉴定。为了确定参与分离的大鼠肝细胞代谢邻氯硝基苯的特定酶,从大鼠中分离出肝亚细胞组分;在NADPH存在下,微体与标记有放射性碳-14(14C)的邻氯硝基苯一起孵化,在 aerobic 条件下产生了邻氯苯胺,SKF 525 A 和甲乙酮对代谢为邻氯苯胺没有影响:这些发现表明细胞色素P-450还原酶负责邻氯硝基苯的还原;放射性标记的邻氯硝基苯也在有或没有微体、细胞质和/或谷胱甘肽的情况下孵化:在细胞质和谷胱甘肽存在的情况下,邻氯硝基苯转化为S-(2-硝基苯基)谷胱甘肽,这表明细胞质谷胱甘肽转移酶参与了这种结合(未指定测试物质的浓度)。
Metabolism in vitro: radiolabelled (14C) o-chloronitrobenzene was incubated with isolated rat hepatocytes. After 90 min., 71% of the o-chloronitrobenzene had been metabolized; the primary metabolic pathway for o-chloronitrobenzene was reduction to o-chloroaniline (19.2% of the total radioactivity); o-chloronitrobenzene was also conjugated with glutathione; two other very polar metabolites, comprising 14.2% of the total 14C from o-chloronitrobenzene, have not been identified. in order to identify the specific enzymes involved in the metabolism of o-chloronitrobenzene by isolated rat hepatocytes, hepatic subcellular fractions were isolated from rats; microsomes incubated with radiolabelled (14C) o-chloronitrobenzene in the presence of NADPH produced o-chloroaniline under aerobic conditions and SKF 525 A and metyrapone had no effect on the metabolism to o-chloroaniline: these findings suggest that cytochrome P-450 reductase is responsible for o-chloronitrobenzene reduction; radiolabelled o-chloronitrobenzene was also incubated with or without microsomes, cytosol and/or glutathione: o-chloronitrobenzene was converted to S-(2-nitrophenyl)glutathione in the presence of cytosol and glutathione suggesting that cytosolic glutathione transferase is involved in this conjugation (concentration of the test substance unspecified).
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 毒性总结
人类健康:一次口服应用后,1--2-硝基苯对人类来说是有毒的,属于中等毒性……;其急性吸入和皮肤毒性为中等……:所有应用途径的主要症状是发绀。1--2-硝基苯对兔子的眼睛有轻微的刺激作用,这种刺激作用在24小时内可逆。由于关于皮肤致敏的有限且质量较差的信息,无法确定该化学物质是否具有致敏活性。在大鼠和小鼠中,重复剂量毒性的靶器官是血液、肝脏、肾脏和脾脏,其中最敏感的参数是变性血红蛋白血症。重复剂量毒性在大鼠和小鼠中通过全身吸入进行了为期13周的研究。在大鼠中未达到NOAEL,LOAEL为1.1 ppm(7 mg/立方米)。在小鼠中,即使在1.1 ppm和2.3 ppm时也观察到了肝脏和肾脏重量的增加。小鼠组织病理学损伤的NOAEL为4.5 ppm(28.8 mg/立方米)。在一项亚急性喂养研究中,小鼠的NOAEL为50 ppm(雄性:16 mg/kg体重/天;雌性:24 mg/kg体重/天)。1--2-硝基苯在细菌测试系统中表现出弱的致突变活性,但在体外哺乳动物细胞测试系统中没有。在果蝇中没有表现出致突变性。在体外哺乳动物细胞中,它表现出弱的裂变活性。该物质诱导了姐妹染色单体交换的增加,但这种效果的生物学相关性尚不清楚。将1--2-硝基苯注入小鼠腹腔内会导致肝脏和肾脏的DNA损伤。现有遗传毒性研究的不一致结果对于硝基芳烃来说是典型的。总的来说,1--2-硝基苯被认为具有遗传毒性,至少是一种弱裂变剂。1--2-硝基苯在大鼠的不同器官和小鼠的肝脏中诱导了肿瘤。根据现有研究,尽管存在方法学缺陷,仍对1--2-硝基苯的致癌潜力表示关注。在F344/N大鼠和B6C3F1小鼠吸入13周后,只有在雄性中1--2-硝基苯影响了生殖器官。进行了一项关于生殖毒性的具体研究(NTP连续繁殖方案),结果显示,尽管口服给药后小鼠品系的肝脏和脾脏重量显著变化,以及变性血红蛋白平升高,但1--2-硝基苯在另一个小鼠品系中没有表现出生殖毒性。因此,Swiss CD-1小鼠口服应用的NOAEL生育为160 mg/kg体重/天,尽管在这个浓度下母鼠表现出一般毒性效应。由于1--2-硝基苯在雄性大鼠和一种小鼠品系的雄性亚慢性吸入系统毒性剂量中影响了生殖器官,因此存在对生殖毒性潜力的关注,尽管在第二种小鼠品系的雄性口服给药后没有检测到繁殖受损。使用Sprague-Dawley大鼠进行了两项发育毒性的研究,这些研究存在方法学缺陷。在其中一项研究中,由于最高剂量平的高死亡率,只能评估两个剂量。母体毒性的NOAEL为25 mg/kg体重/天,由于特定骨骼变异的窝数增加,无法得出明确的发育毒性NOAEL。在第二项研究中只应用了一个剂量:发育毒性的NOAEL为100 mg/kg体重/天,无法得出母体毒性的NOAEL。根据现有研究,总体结论是,尽管研究存在一些局限性,但没有发育毒性的迹象。 环境:……急性毒性已确定为:鱼类(Cyprinus carpio)的96小时LC50为25.5 mg/L;蚤(Daphnia magna)的24小时EC50为12 mg/L,48小时EC50为23.9 mg/L,蚤(Daphnia carinata)的48小时EC50为21.3 mg/L;藻类(Chlorella pyrenoidosa)的96小时-EbC50为6.9 mg/L。另一种藻类(SECendesmus subspicatus)的48小时-ErC50为75 mg/L,48小时-ErC10为19 mg/L。对蚤(Daphnia magna)进行了慢性毒性测试,21天NOEC为3 mg/L,针对繁殖(测量浓度),对鱼类(Pimephales promelas)进行了早期生活阶段测试,33天NOEC为0.264 mg/L,针对正常幼虫(测量浓度)。使用评估因子10,得出PNECaqua为0.026 mg/L。在土壤中进行的植物测试中,对生菜(Lactuca sativa)的14天EC50在3.2 - 10 mg/kg土壤干重范围内,针对生长端点。从这个值中使用评估因子1000,得出APNECsoil为
Human Health: After single oral application 1-chloro-2-nitrobenzene is toxic to moderate toxic ... ; the acute inhalative and dermal toxicity is moderate ...: Cyanotic appearance was the predominant symptom for all routes of application. ... 1-Chloro-2-nitrobenzene caused slight irritation effects to the eyes of rabbits, which were reversible within 24 hours. Due to the limited and poor quality information available regarding skin sensitization, it cannot be concluded whether or not the chemical has a sensitizing activity. Target organs of repeated dose toxicity in rats and mice are blood, liver, kidney and spleen with methemogobinemia as the most sensitive parameter. The repeated dose toxicity was examined in rats and in mice for a period of 13 weeks via whole body inhalation. The NOAEL in rats was not achieved, the LOAEL is 1.1 ppm (7 mg/cu m). In mice, increased liver and kidney weights were observed even at 1.1 ppm and respectively 2.3 ppm. The NOAEL for histopathological injury in mice is 4.5 ppm (28.8 mg/cu m). In a subacute feeding study with mice the NOAEL was 50 ppm (males: 16 mg/kg bw/day; females: 24 mg/kg bw/day). 1-Chloro-2-nitrobenzene showed weak mutagenic activity in bacterial test systems but not in mammalian cell test systems in vitro. It was not mutagenic in Drosophila melanogaster . In mammalian cells in vitro, it showed weak clastogenic activity. The substance induced increased rates of Sister Chromatid Exchanges, whereas the biological relevance of this effect is not yet clear. Intraperitoneal injection into mice resulted in DNA damage in the liver and kidney. The inconsistent results of the available genotoxic studies are typical for nitroaromatics. As a whole 1- chloro-2-nitrobenzene is suspected of being genotoxic, at least a weak clastogen. 1-Chloro-2-nitrobenzene induced tumors in different organs of rats and in the liver of mice. Based on the available studies, which have methodological deficiencies, there is a concern for a carcinogenic potential of 1-chloro-2- nitrobenzene. Following inhalative exposure of F344/N rats and B6C3F1 mice for 13 weeks, only in males 1- chloro-2-nitrobenzene affects the reproductive organs. Performance of a specific study on toxicity to reproduction (NTP continuous breeding protocol) reveals that 1-chloro-2-nitrobenzene was without reproductive toxicity in a different mice strain following oral treatment by gavage despite of significant changes in liver and spleen weight and despite of elevated methaemoglobin levels. Thus, the NOAEL fertility in Swiss CD-1 mice after oral application is 160 mg/kg bw/day whereas the dams showed general toxicity effects at this concentration. Because 1-choro-2- nitrobenzene affected the reproductive organs in systemic toxic doses in male rats and in males of one strain of mice after subchronic inhalation there is a concern for a reproductive toxicity potential, even if an impairment of reproduction after oral administration in males of a second strain of mice could not be detected. Developmental toxicity was examined by two studies with Sprague-Dawley rats which have methodology deficiencies. In one study, due to high mortality rate at the highest dose level, only two doses could be evaluated. NOAEL maternal toxicity is 25 mg/kg bw/day, a NOAEL developmental toxicity could not be conclusively derived since there was an increase in the number of litters exhibiting specific skeletal variations. In the second study only one dose was applied: NOAEL developmental toxicity is 100 mg/kg bw/day, a NOAEL maternal toxicity could not be derived. Based on the available studies the overall conclusion is, that there is no indication of developmental toxicity, although there are some limitations within the studies. Environment: ... The acute toxicity has been determined for: fish (Cyprinus carpio) with a 96 hr-LC50 of 25.5 mg/L; daphnia (Daphnia magna) with a 24 hr-EC50of 12 mg/L and a 48 hr-EC50 of 23.9 mg/L, and Daphnia carinata with a 48 hr-EC50 of 21.3 mg/L; algae (Chlorella pyrenoidosa) with a 96 hr-EbC50 of 6.9 mg/L. With another alga species (Secendesmus subspicatus) a 48 hr-ErC50 of 75 mg/L and a 48h-ErC10 of 19 mg/L was found. Chronic toxicity has been tested for Daphnia magna with a 21 d-NOEC of 3 mg/L on reproduction (measured concentration) and for fish (Pimephales promelas) in an Early Life Stage Test with a 33 d-NOEC of 0.264 mg/L concerning the endpoint normal larvae (measured concentration). A PNECaqua of 0.026 mg/L is derived using an assessment factor of 10. In a test with terrestrial plants a 14 d-EC50 in the range of 3.2 - 10 mg/kg soil dry weight was determined for Lactuca sativa regarding the endpoint of growth. APNECsoil of 3.2 ug/kg bw was derived from this value using an assessment factor of 1000.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌性证据
评价:对于氯硝基苯在人类中的致癌性,证据不足。对于氯硝基苯在实验动物中的致癌性,证据也不足。总体评价:氯硝基苯对人类的致癌性无法分类(第3组)。/氯硝基苯/
Evaluation: There is inadequate evidence in humans for the carcinogenicity of chloronitrobenzenes. There is inadequate evidence in experimental animals for the carcinogenicity of chloronitrobenzenes. Overall evaluation: Chloronitrobenzenes are not classifiable as to their carcinogenicity to humans (Group 3). /Chloronitrobenzenes/
来源:Hazardous Substances Data Bank (HSDB)
毒理性
  • 致癌物分类
国际癌症研究机构致癌物:2-氯硝基苯
IARC Carcinogenic Agent:2-Chloronitrobenzene
来源:International Agency for Research on Cancer (IARC)
毒理性
  • 致癌物分类
国际癌症研究机构(IARC)致癌物分类:2B组:可能对人类致癌
IARC Carcinogenic Classes:Group 2B: Possibly carcinogenic to humans
来源:International Agency for Research on Cancer (IARC)
毒理性
  • 致癌物分类
国际癌症研究机构专著:第65卷:(1996年)印刷工艺和印刷油墨,黑及一些硝基化合物
IARC Monographs:Volume 65: (1996) Printing Processes and Printing Inks, Carbon Black and Some Nitro Compounds
来源:International Agency for Research on Cancer (IARC)
吸收、分配和排泄
研究了剂量对2-氯硝基苯和4-氯硝基苯在大鼠皮肤吸收的影响。将(14)C标记的2-氯硝基苯或4-氯硝基苯涂抹在雄性Fischer 344大鼠剃光的背部,应用速率相当于0、0.65、6.5或65 mg/kg的剂量。收集24、48或72小时的尿液和粪便样本,并测定(14)C活性。用乙醇阱收集呼出的挥发性物质并进行分析。72小时后,大鼠被处死,取出皮肤并分析(14)C活性。大约21-27%的2-氯硝基苯剂量和43至45%的4-氯硝基苯剂量在72小时内通过尿液排出。大约11至15%的2-氯硝基苯剂量和5至12%的4-氯硝基苯剂量在72小时内被排出。4-氯硝基苯的粪便排泄显示出与剂量相关的增加,仅在比较65 mg/kg剂量和0.65 mg/kg剂量时统计学上显著。大约27至32%的2-氯硝基苯衍生放射性活性和13至15%的4-氯硝基苯衍生(14)C活性在乙醇阱中回收。收集到的放射性活性的量不依赖于剂量,且由未改变的2-氯硝基苯或4-氯硝基苯组成。...对所有(14)C数据进行分析表明,2-氯硝基苯的皮肤吸收在整个剂量范围内是线性的。4-氯硝基苯的皮肤吸收仅在应用0.65和6.5 mg/kg剂量后呈线性。/结果表明/,在所使用的实验条件下,至少有33至40%的2-氯硝基苯剂量和51至62%的4-氯硝基苯剂量从大鼠皮肤被吸收。...2-氯硝基苯的皮肤吸收在0.65 mg/kg至65 mg/kg的剂量范围内是线性的。4-氯硝基苯的皮肤吸收基本上不受剂量影响。
The effect of dose on the dermal absorption of 2-chloronitrobenzene and 4-chloronitrobenzene was studied in rats. (14)C labeled 2-chloronitrobenzene or 4-chloronitrobenzene was applied to the shaved backs of male Fischer 344 rats at an application rates equivalent to doses of 0, 0.65, 6.5 or 65 mg/kg. Urine and feces samples were collected for 24, 48 or 72 hr and assayed for (14)C activity. Exhaled volatiles were collected in ethanol traps and analyzed. After 72 hr, the rats were /sacrificed/ and their skin removed and analyzed for (14)C activity. Approx 21-27% and 43 to 45% of the 2-chloronitrobenzene and 4-chloronitrobenzene doses, respectively, were eliminated in the urine over 72 hr. Approx 11 to 15% of the 2-chloronitrobenzene dose and 5 to 12% of the 4-chloronitrobenzene dose were excreted over 72 hr. Fecal excretion of 4-chloronitrobenzene showed a dose related incr which was statistically significant only when comparing the 65 mg/kg dose with the 0.65 mg/kg dose. Approx 27 to 32% of 2-chloronitrobenzene derived radioactivity and 13 to 15% of the 4-chloronitrobenzene derived (14)C activity were recovered in the ethanol traps. The amt of collected radioactivity did not depend on dose and consisted of unchanged 2-chloronitrobenzene or 4-chloronitrobenzene. ... An analysis of all (14)C data indicated that the dermal absorption of 2-chloronitrobenzene ... was linear over the entire dose range. Dermal absorption of 4-chloronitrobenzene was linear only after application of 0.65 and 6.5 mg/kg. /Results indicate/ that under the experimental conditions used at least 33 to 40% and 51 to 62% of the applied 2-chloronitrobenzene and 4-chloronitrobenzene doses, respectively, are absorbed from the skin of rats. ... Dermal absorption of 2-chloronitrobenzene is linear over the dose range 0.65 mg/kg to 65 mg/kg. Dermal absorption of 4-chloronitrobenzene is essentially unaffected by dose.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
...化学物质的皮肤吸收进行了比较,并在给予雄性F344/N大鼠口服后,部分表征了吸收、分布、代谢和排泄。在大鼠中展示了[14C]-2-氯硝基苯和[14C]-4-氯硝基苯的经皮吸收。在非封闭条件下,对于0.65至65毫克/千克的剂量范围,33%至40%的2-氯硝基苯和51%至62%的4-氯硝基苯被吸收。口服吸收比皮肤吸收略高,代谢复杂,从给予2-氯硝基苯或4-氯硝基苯的大鼠尿液中分离出超过20种未识别的代谢物。
... The dermal absorption of the chemicals was compared, and the absorption, distribution, metabolism, and excretion were partially characterized following oral administration to male F344/N rats. Percutaneous absorption of [14C]-2-chloronitrobenzene and [14C]-4-chloronitrobenzene was demonstrated in rats. For doses ranging from 0.65 to 65 mg/kg of either chemical, 33%; to 40%; of 2-chloronitrobenzene and 51%; to 62%; of 4-chloronitrobenzene were absorbed under nonocclusive conditions. Oral absorption was somewhat higher than dermal absorption for both chemicals, and metabolism was complicated, with over 20 unidentified metabolites isolated from urine of rats given either 2- or 4-chloronitrobenzene.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
1--2-硝基苯在适当的暴露条件下,可以通过皮肤、胃肠道以及呼吸道被人体吸收。用标记化学物质进行的大鼠研究表明,口服给药后1--2-硝基苯的吸收率为80%,经开放性皮肤应用后至少为40%。在连续11天中,成年大鼠和老龄大鼠通过灌胃给药65 mg/kg bw的1--2-硝基苯。在第1、5和9天应用标记物质,并在接下来的96小时内收集尿液和粪便。成年大鼠通过尿液排出71-74%的剂量,通过粪便排出20-27%的剂量。随着治疗时间的延长,排泄率增加。老龄大鼠的尿液排泄率为71-85%,并未随治疗时间延长而增加。在d9治疗后的72小时确定组织中放射性平的检测结果发现,成年大鼠体内组织中有5%的剂量,老龄大鼠中有8%。在非常高的剂量下,例如口服给予200 mg/kg bw,尿液排泄会延迟,粪便排泄会明显受到抑制。有证据表明肠道-肝脏循环的参与,但没有迹象表明1--2-硝基苯或其代谢物之一有积累现象。
1-Chloro-2-nitrobenzene, under appropriate conditions of exposure, is absorbed by the body both via the skin and the gastrointestinal tract as well as via the respiratory tract. Rat studies with labelled chemical show that 1-chloro-2-nitrobenzene absorption is 80% following oral administration and at least 40% after open dermal application. 0n 11 consecutive days, 65 mg 1-chloro-2-nitrobenzene/kg bw was administered by gavage to adult and to old rats. On days 1, 5, and 9 applied substance was labelled and urine and feces were collected in the following 96 hours. The adult rats excreted 71-74% of the dose in the urine and 20-27% of the dose in the feces. Excretion rate increased with the duration of treatment. Urinary excretion rate in the old rats consisted 71-85% of the dose and did not increase with the duration of treatment. The radioactivity level in the tissues were determined 72 hours after d9-treatment and shown to be found 5% of the dose in adult rats and 8% in the old rats. At very high doses, e.g. 200 mg/kg bw given orally, urinary excretion is delayed and fecal excretion is markedly suppressed. There is evidence to suggest involvement of the enterohepatic cycle, but there are no signs of accumulation of 1-chloro-2-nitrobenzene or one of its metabolites.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
经口服给予家兔100毫克/千克体重的对氯硝基苯后,剂量的42%以葡萄糖苷酸形式从尿液中排出,24%以硫酸盐形式排出,7%以巯基尿酸形式排出,9%以自由形态的2-氯苯胺排出。仅在粪便中检测到0.3%的2-氯苯胺。给药后48小时,排出完全。
After oral administration of 100 mg 1-chloro-2-nitrobenzene/kg bw to rabbits 42% of the dose was excreted in the urine as glucuronides, 24% as sulfates, 7% as mercapturic acids and 9% as free 2-chloroaniline. Only 2-Chloroaniline (0.3%) could be detected in the feces. 48 hours after administration elimination was complete.
来源:Hazardous Substances Data Bank (HSDB)

安全信息

  • 危险等级:
    6.1
  • 安全说明:
    S28A,S36/37/39,S38,S45,S60
  • 危险品运输编号:
    UN 1578 6.1/PG 2
  • WGK Germany:
    2
  • 海关编码:
    29049085
  • 危险类别:
    6.1
  • 危险品标志:
    T
  • 危险类别码:
    R22,R24,R52/53
  • RTECS号:
    CZ0875000
  • 包装等级:
    II

SDS

SDS:ab901672714b9ea7ded0e818fdc06b66
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制备方法与用途

类别:有毒物质

可燃性危险特性:可燃,燃烧时分解产生有毒的化物和氮氧化物气体。

储运特性:应存放在低温、通风且干燥的地方;需防火措施,并与强氧化剂分开存放。

灭火剂:可用二氧化碳、干粉或砂土进行灭火。

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
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量
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    • 2
    • 3

反应信息

  • 作为反应物:
    描述:
    参考文献:
    名称:
    Rikliss, 1940, vol. 7, p. 154
    摘要:
    DOI:
  • 作为产物:
    描述:
    1,2-二硝基苯高氯酸硫酸 、 sodium nitrite 、 盐酸 作用下, 以 乙酸乙酯 为溶剂, 以63%的产率得到硝基氯苯
    参考文献:
    名称:
    芳基重氮盐的两相电化学生成:在电生成的铜催化的桑德迈尔反应中的应用。
    摘要:
    首次报道了在两相系统(乙酸乙酯/水)中由硝基芳烃电化学生成芳基重氮盐。以良好的收率和良好的纯度制备了包括偶氮,偶氮砜和芳基叠氮化物在内的一些化合物。阴极产生的芳基重氮和阳极产生的铜(I)离子用于进行Sandmeyer反应。为了改进该方法,引入了以Zn棒为阳极的H型自驱动电池,并将其用于两相芳基重氮的生产。
    DOI:
    10.1021/acs.orglett.0c02013
  • 作为试剂:
    描述:
    N-甲基哌啶氯化苄硝基氯苯 作用下, 反应 24.0h, 生成 1-benzyl-1-methylpiperidinium chloride
    参考文献:
    名称:
    元素硫通过氧化还原策略介导的环化:由邻氯硝基苯和苄基氯合成苯并噻唑
    摘要:
    已经开发了一种新的无金属的合成方法,该方法使用元素硫作为无痕氧化剂,由易于获得的邻氯硝基苯和苄基氯合成2-取代的苯并噻唑。该协议提供了一种简单,有效且原子经济的方法来以中等至优异的产率获得苯并噻唑。并且该方法表现出良好的官能团耐受性。
    DOI:
    10.1016/j.tet.2017.07.013
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文献信息

  • Npy antagonists, preparation and uses
    申请人:Botez Iuliana
    公开号:US20090233910A1
    公开(公告)日:2009-09-17
    The present invention concerns novel compounds, their preparation and their uses, therapeutic uses in particular. More specifically it concerns derivative compounds having at least two aromatic cycles, their preparation and their uses, in particular in the area of human or animal health. These compounds have an affinity for the biological receptors of neuropeptide Y, NPY, present in the central and peripheral nervous systems. The compounds of the invention are preferably NPY antagonists, and more particularly antagonists of sub-type NPY Y1, and can therefore be used for the therapeutic or prophylactic treatment of any disorder involving NPY. The present invention also concerns pharmaceutical compositions containing said compounds, their preparation and their uses, as well as treatment methods using said compounds.
    本发明涉及新颖化合物,它们的制备和用途,特别是在治疗方面的用途。更具体地说,它涉及至少具有两个芳香环的衍生化合物,它们的制备和用途,特别是在人类或动物健康领域。这些化合物对存在于中枢和外周神经系统中的神经肽Y(NPY)的生物受体具有亲和力。本发明的化合物优选为NPY拮抗剂,更具体地说是NPY Y1亚型的拮抗剂,因此可用于治疗或预防涉及NPY的任何疾病。本发明还涉及含有所述化合物的药物组合物,其制备和用途,以及使用所述化合物的治疗方法。
  • Synthesis of near-infrared fluorescent rhodamines <i>via</i> an S<sub>N</sub>Ar<sup>H</sup> reaction and their biological applications
    作者:Qing Wang、Kun Huang、Songtao Cai、Chang Liu、Xiaojie Jiao、Song He、Liancheng Zhao、Xianshun Zeng
    DOI:10.1039/c8ob01701h
    日期:——
    the preparation of a wide variety of π-extended near-infrared fluorescent rhodamine dyes. Using this strategy, seven rectilinearly π-extended rhodamines (RE1–RE7) that had fluorescence emission wavelengths in the near-infrared region were synthesized. RE1, RE3, and RE4 were lysosome targetable and showed good photostabilities. In addition, using dye RE1 as a precursor, we constructed a novel NIR fluorescent
    由于减少了来自生物样品的干扰吸收和荧光,减少了散射并提高了组织穿透深度,近红外(NIR)染料生物医学中引起了人们的极大兴趣。在这种情况下,我们报告了使用芳香族氢的独特分子内亲核取代(S N Ar H)策略合成直线π延伸的若丹明染料的方法。该策略利用了预先组织的芳族基氮与x吨离子中电子不足的碳之间的S N Ar H反应。S N Ar H本文提出的反应可在没有过渡属催化剂的温和条件下进行,并且有望实现多种π扩展的近红外荧光若丹明染料的制备。使用这种策略,合成了在近红外区域具有荧光发射波长的七个直线π扩展的若丹明(RE1-RE7)。RE1,RE3和RE4可溶酶体靶向,并显示出良好的光稳定性。此外,我们以染料RE1为前体,构建了一种新型的NIR荧光开启探针(RE1-Cu),可用于检测Cu 2+ 在活细胞中的含量,证明了我们近红外功能荧光染料的价值。
  • Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ
    作者:Woonphil Baik、Wanqiang Luan、Hyun Joo Lee、Cheol Hun Yoon、Sangho Koo、Byeong Hyo Kim
    DOI:10.1139/v05-026
    日期:2005.3.1

    Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually <7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides. Key words: aminoarenes, haloarenes, halodimethylsulfonium halide, halogenation, amination.

    二甲基亚砜卤化物1是一种良好的亲核卤化物,可在现场由氢卤酸和二甲亚砜形成。这种活化的亲核卤化物迅速将由相同的氢卤酸和亚硝酸根在现场制备的芳基重氮盐转化为芳基化物、化物或化物,收率较高。在DMSO中,亚硝酸根和氢卤酸的联合作用是直接转化芳香胺的必要条件,从而在1小时内产生芳基卤化物。带有电子给体或吸引基团或有立体位阻的芳香胺的取代化合物也可顺利转化为相应的芳香卤化物。观察到的唯一副产物是去芳烃(通常<7%)。孤立的芳基重氮盐也可以使用1转化为相应的芳基卤化物。该方法提供了一种简便的、一步法的程序,用于将芳烃转化为卤代芳烃,并且不伴随通常伴随使用卤化物进行桑迈尔反应的环境污染物。关键词:芳烃,卤代芳烃,卤二甲基亚砜卤化物,卤化,胺化。
  • Highly chemoselective reduction of nitroarenes over non-noble metal nickel-molybdenum oxide catalysts
    作者:Haigen Huang、Xueguang Wang、Xu Li、Chenju Chen、Xiujing Zou、Weizhong Ding、Xionggang Lu
    DOI:10.1039/c6gc03141b
    日期:——
    Chemoselective reduction of nitroarenes is an important transformation for the production of arylamines, which are the primary intermediates in the synthesis of pharmaceuticals, agrochemicals and dyes. Heterogeneous non-noble metal nickel-molybdenum...
    硝基芳烃化学选择性还原是生产芳胺的重要转变,芳胺是合成药物,农药和染料的主要中间体。非均质非贵
  • Recyclable and Selective Nitroarene Hydrogenation Catalysts Based on Carbon-Coated Cobalt Oxide Nanoparticles
    作者:Bingfeng Chen、Fengbo Li、Zhijun Huang、Guoqing Yuan
    DOI:10.1002/cctc.201501265
    日期:2016.3.18
    through direct heating treatment of cobalt oxide precursors incipiently deposited over nanographite materials. Cobalt oxides are partially reduced to active zero‐valent metal species and the simultaneous formation of carbon layers over the nanoparticles protects them from oxidation and deactivation. This nanocatalyst performs excellently in chemoselective hydrogenation of some challenging nitroarenes with
    通过直接加热处理刚沉积在纳米石墨材料上的氧化钴前体,已开发出涂覆有石墨烯层(Co / CoO @碳)的Co / CoO纳米颗粒。氧化钴被部分还原为活性零价属,同时在纳米颗粒上同时形成碳层可保护其免受氧化和失活。这种纳米催化剂在某些具有挑战性的硝基芳烃化学选择性加氢中具有出色的性能,且其官能团可还原为相应的苯胺。在十次循环测试中,催化剂保持了主动和选择性的性能。
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表征谱图

  • 氢谱
    1HNMR
  • 质谱
    MS
  • 碳谱
    13CNMR
  • 红外
    IR
  • 拉曼
    Raman
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mass
cnmr
ir
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  • 峰位数据
  • 峰位匹配
  • 表征信息
Shift(ppm)
Intensity
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Assign
Shift(ppm)
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测试频率
样品用量
溶剂
溶剂用量
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同类化合物

(βS)-β-氨基-4-(4-羟基苯氧基)-3,5-二碘苯甲丙醇 (S,S)-邻甲苯基-DIPAMP (S)-(-)-7'-〔4(S)-(苄基)恶唑-2-基]-7-二(3,5-二-叔丁基苯基)膦基-2,2',3,3'-四氢-1,1-螺二氢茚 (S)-盐酸沙丁胺醇 (S)-3-(叔丁基)-4-(2,6-二甲氧基苯基)-2,3-二氢苯并[d][1,3]氧磷杂环戊二烯 (S)-2,2'-双[双(3,5-三氟甲基苯基)膦基]-4,4',6,6'-四甲氧基联苯 (S)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (R)富马酸托特罗定 (R)-(-)-盐酸尼古地平 (R)-(-)-4,12-双(二苯基膦基)[2.2]对环芳烷(1,5环辛二烯)铑(I)四氟硼酸盐 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[((6-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(4-叔丁基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-7-双(3,5-二叔丁基苯基)膦基7''-[(3-甲基吡啶-2-基甲基)氨基]-2,2'',3,3''-四氢-1,1''-螺双茚满 (R)-(+)-4,7-双(3,5-二-叔丁基苯基)膦基-7“-[(吡啶-2-基甲基)氨基]-2,2”,3,3'-四氢1,1'-螺二茚满 (R)-3-(叔丁基)-4-(2,6-二苯氧基苯基)-2,3-二氢苯并[d][1,3]氧杂磷杂环戊烯 (R)-2-[((二苯基膦基)甲基]吡咯烷 (R)-1-[3,5-双(三氟甲基)苯基]-3-[1-(二甲基氨基)-3-甲基丁烷-2-基]硫脲 (N-(4-甲氧基苯基)-N-甲基-3-(1-哌啶基)丙-2-烯酰胺) (5-溴-2-羟基苯基)-4-氯苯甲酮 (5-溴-2-氯苯基)(4-羟基苯基)甲酮 (5-氧代-3-苯基-2,5-二氢-1,2,3,4-oxatriazol-3-鎓) (4S,5R)-4-甲基-5-苯基-1,2,3-氧代噻唑烷-2,2-二氧化物-3-羧酸叔丁酯 (4S,4''S)-2,2''-亚环戊基双[4,5-二氢-4-(苯甲基)恶唑] (4-溴苯基)-[2-氟-4-[6-[甲基(丙-2-烯基)氨基]己氧基]苯基]甲酮 (4-丁氧基苯甲基)三苯基溴化磷 (3aR,8aR)-(-)-4,4,8,8-四(3,5-二甲基苯基)四氢-2,2-二甲基-6-苯基-1,3-二氧戊环[4,5-e]二恶唑磷 (3aR,6aS)-5-氧代六氢环戊基[c]吡咯-2(1H)-羧酸酯 (2Z)-3-[[(4-氯苯基)氨基]-2-氰基丙烯酸乙酯 (2S,3S,5S)-5-(叔丁氧基甲酰氨基)-2-(N-5-噻唑基-甲氧羰基)氨基-1,6-二苯基-3-羟基己烷 (2S,2''S,3S,3''S)-3,3''-二叔丁基-4,4''-双(2,6-二甲氧基苯基)-2,2'',3,3''-四氢-2,2''-联苯并[d][1,3]氧杂磷杂戊环 (2S)-(-)-2-{[[[[3,5-双(氟代甲基)苯基]氨基]硫代甲基]氨基}-N-(二苯基甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[((1S,2S)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2S)-2-[[[[[[((1R,2R)-2-氨基环己基]氨基]硫代甲基]氨基]-N-(二苯甲基)-N,3,3-三甲基丁酰胺 (2-硝基苯基)磷酸三酰胺 (2,6-二氯苯基)乙酰氯 (2,3-二甲氧基-5-甲基苯基)硼酸 (1S,2S,3S,5S)-5-叠氮基-3-(苯基甲氧基)-2-[(苯基甲氧基)甲基]环戊醇 (1S,2S,3R,5R)-2-(苄氧基)甲基-6-氧杂双环[3.1.0]己-3-醇 (1-(4-氟苯基)环丙基)甲胺盐酸盐 (1-(3-溴苯基)环丁基)甲胺盐酸盐 (1-(2-氯苯基)环丁基)甲胺盐酸盐 (1-(2-氟苯基)环丙基)甲胺盐酸盐 (1-(2,6-二氟苯基)环丙基)甲胺盐酸盐 (-)-去甲基西布曲明 龙蒿油 龙胆酸钠 龙胆酸叔丁酯 龙胆酸 龙胆紫-d6 龙胆紫