2,4-二氯苯胺 - CAS号 554-00-7

物化性质

熔点：

59-62 °C (lit.) 60-65 °C
沸点：

245 °C (lit.)
密度：

1.567
闪点：

115°C
溶解度：

可溶于甲醇：，透明，淡的棕黄色
LogP：

2.78 at 20℃
物理描述：

2,4-dichloroaniline appears as beige crystals. (NTP, 1992)
颜色/状态：

PRISMS FROM ACETONE; NEEDLES FROM DILUTED ALCOHOL OR PETROLEUM ETHER
蒸汽密度：

Relative vapor density (air = 1): 5.6
蒸汽压力：

Vapor pressure, Pa at 25 °C:
分解：

370 °C. Decomposes on burning. This produces toxic fumes including nitrogen oxides and hydrogen chloride (see ICSC 0163).
解离常数：

pKa= 2.00 (conjugate acid)
保留指数：

1286;1286;1286;1284;1287;1287
稳定性/保质期：
1. 稳定性^[12]
  - 稳定
2. 禁配物^[13]
  - 酸类、酰基氯、酸酐、强氧化剂
3. 应避免的接触条件^[14]
  - 受热
4. 聚合危害^[15]
  - 不聚合
5. 分解产物^[16]
  - 氯化氢

计算性质

辛醇/水分配系数(LogP)：

2.9
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：

26
氢给体数：

1
氢受体数：

1

ADMET

代谢

四个标记有放射性碳-14的硫双（甲酰胺）类杀虫剂在Sprague Dawley大鼠和ICR小鼠体内的代谢情况被研究。这些杀虫剂源自一系列2,4-二取代苯胺。研究的化合物包括2,4-二氯苯胺。每种化合物都以玉米油溶液口服给药给2只雌性大鼠和4只雌性小鼠，剂量为10-13毫克/千克。在每种情况下，除了二氯系列外，相应的苯胺以自由苯胺的形式被检测到，含量较少。在研究的化合物之间没有观察到显著差异。所有四种化合物的总体代谢方案相似。这些化合物的代谢涉及在胃中迅速水解母体化合物为简单甲酰胺，然后转化为具有各种代谢命运的N-甲酰苯胺，尤其是通过甲基基团的氧化。

The metabolism of four (14)C-labeled thiobis(formamidine) insecticides was studied in Sprague Dawley rats & ICR mice. The insecticides were derived from a series of 2,4-disubstituted anilines. The compounds studied included 2,4-dichloroaniline. Each compound was orally admin in corn oil solution to 2 female rats & 4 female mice in doses of 10-13 mg/kg. In every case, the corresponding anilines were detected as free aniline, in minor amounts except for the dichloro series. There were no significant differences observed between the compounds studied. The general metabolism schemes for all 4 compounds were similar. Metabolism of these compounds involves rapid hydrolysis of the parent compound in the stomach to simple formamidine, which is then converted to an N-formylaniline that has various metabolic fates, particularly through oxidation of methyl groups.

来源:Hazardous Substances Data Bank (HSDB)

代谢

为了揭示对氯硝基苯（CNB）的尿代谢物，进行了一项研究，通过气相色谱/质谱法分离和鉴定大鼠给药后尿中的代谢物。六只雄性SD大鼠单次腹腔注射100mg/kg CNB，稀释在橄榄油中。从六只大鼠中收集了接触后8到24小时内的尿液。在大鼠尿液中检测到微量的未改变的CNB，但大部分CNB似乎在排泄前已被代谢。确定了九种物质：对氯苯胺、2,4-二氯苯胺、对硝基苯酚、2-氯-5-硝基苯酚、2-氨基-5-氯苯酚、对氯甲醛、4-氯-2-羟基乙酰苯胺、少量的对氯乙酰苯胺和微量的未改变的CNB。

In order to reveal the urinary metabolites of p-chloronitrobenzene (CNB), an investigation was conducted to separate and identify urinary metabolites by gas chromatography/mass spectrometry following the administration of the compound to rats. Six male Sprague-Dawley-rats were given a single dose of 100 mg/kg CNB diluted in olive-oil and injected intraperitoneally. Urine was collected from the six rats at from 8 to 24 hours after exposure. Trace amounts of unchanged CNB were detected in the urine of the rats, but most of the CNB appeared to have been metabolized prior to excretion. Nine substances were identified: p-chloroaniline, 2,4-dichloroaniline, p-nitrothiophenol, 2-chloro-5-nitrophenol, 2-amino-5-chlorophenol, p-chloroformanilide, 4-chloro-2-hydroxyacetanilide, a small amount of p-chloroacetanilide and traces of unchanged CNB.

来源:Hazardous Substances Data Bank (HSDB)

代谢

p-氯硝基苯（p-CNB）在人体中的尿液代谢物通过急性中毒患者的尿液样本进行了确定。这六名患者是在装卸破损的p-CNB袋子时接触到p-CNB的码头工人，随后被送往医院。利用p-CNB代谢物随时间变化的尿液排泄率曲线进行矩分析和室模型分析，以进行药物代谢动力学评估。研究发现，六名受试者每种代谢物排泄量与五种代谢物总量的平均比值和平均滞留时间分别为：2-氯-5-硝基酚（619103）为12.2%和6.7天，N-乙酰-S-(4-硝基苯基)-L-半胱氨酸为48.0%和7.0天，2,4-二氯苯胺为1.2%和3.7天，p-氯苯胺为29.9%和10.0天，2-氨基-5-氯酚为8.7%和6.0天。p-CNB转化为2-氯-5-硝基酚和p-氯苯胺的速度似乎较慢，但生成的p-氯苯胺在人体内相对较快地被代谢。作者指出，五种代谢物的排泄量比值在受试者之间几乎是恒定的，而母体化合物的代谢速率和平均滞留时间在个体之间存在较大差异。

The urinary metabolites of p-chloronitrobenzene (p-CNB) in humans were determined using urine samples from acutely poisoned subjects. The six subjects were longshoremen hospitalized after being exposed to p-CNB while loading torn bags of the substance. Moment analysis and compartment model analysis of the urinary excretion rate of metabolites of p-CNB versus time curves were used for the pharmacokinetic evaluation. The findings suggest that the average values of the ratio of excreted amount of each metabolite to the total amount of the five metabolites and mean residence time in the six subjects were, respectively, 12.2% and 6.7 days for 2-chloro-5-nitrophenol (619103), 48.0% and 7.0 days for N-acetyl-S-(4-nitrophenyl)-L-cysteine, 1.2% and 3.7 days for 2,4-dichloroaniline, 29.9% and 10.0 days for p-chloroaniline, and 8.7% and 6.0 days for 2-amino-5-chlorophenol. The rates of transformation of p-CNB to 2-chloro-5-nitrophenol and p-chloroaniline appeared to be slow, but the resulting p-chloroaniline was metabolized relatively rapidly in the human body. The authors note that the ratio of the excretion amounts of the five metabolites was nearly constant among the subjects, whereas the rate of metabolism of the parent compound and the mean residence time varied widely among the individuals.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

暴露途径

这种物质可以通过吸入、皮肤接触和摄入被身体吸收。

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.