2,4-二氨基甲苯 | 95-80-7

• 物质功能分类: 化学试剂 - 有机试剂 - 多胺
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4-二氨基甲苯
• 中文别名: 甲苯-2,4-二胺；2.4-甲苯二胺；2,4-二氨基甲；2,4-二胺；4-甲基间苯二胺；间甲苯二胺；4-甲基-1,3-苯二胺；2,4-二胺基甲苯
• 英文名称: 2,4-Diaminotoluene
• 英文别名: 4-methylbenzene-1,3-diamine；2,4-toluenediamine；5-amino-o-toluidine；2,4-DAT
• CAS: 95-80-7；91696-44-5
• 化学式: C₇H₁₀N₂
• mdl: MFCD00007804
• 分子量: 122.17
• InChiKey: VOZKAJLKRJDJLL-UHFFFAOYSA-N

物化性质

• 熔点：
  97-99 °C(lit.)
• 沸点：
  283-285 °C(lit.)
• 密度：
  1.26 g/cm3 (20℃)
• 闪点：
  149 °C
• 溶解度：
  38克/升
• 暴露限值：
  Carcinogenicity: Animal Sufficient Evidence (IARC); no TWA assigned (because it is a carcinogen, there should be no exposure to this compound).
• LogP：
  0.074 at 20℃
• 物理描述：
  2,4-toluenediamine appears as a colorless crystalline solid. Toxic by ingestion and inhalation. Irritates skin and eyes. Slightly soluble in water and neutrally buoyant in water. Decomposes with emission of toxic oxides of nitrogen at high temperatures. Used in making dyes.
• 颜色/状态：
  Needles from water; crystals from alcohol
• 蒸汽密度：
  Relative vapor density (air = 1): 4.2
• 蒸汽压力：
  1.70X10-4 mm Hg at 25 °C
• 大气OH速率常数：
  1.92e-10 cm3/molecule*sec
• 稳定性/保质期：

  Readily becomes oxidized in neutral or alkaline soln to form dark products

• 自燃温度：
  475 °C
• 分解：
  When heated to decomposition it emits toxic fumes of nitrogen oxides.

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  52
• 氢给体数：
  2
• 氢受体数：
  2

ADMET

代谢

在多种啮齿类动物中，主要的尿液代谢物是2,4-二氨基-5-羟基甲苯；也发现了N-乙酰化和葡萄糖醛酸苷结合物。在大鼠中，尿液中主要的未结合代谢物是4-乙酰氨基-2-氨基甲苯、2,4-二乙酰氨基甲苯和2,4-二乙酰氨基苯甲酸。

... In several rodent species the major urinary metabolite was 2,4-diamino-5-hydroxytoluene; n-acetyl & glucuronide conjugates were also found. In rats the major unconjugated metabolites in urine are 4-acetylamino-2-aminotoluene, 2,4-diacetylaminotoluene & 2,4-diacetylaminobenzoic acid.

来源:Hazardous Substances Data Bank (HSDB)

代谢

当2,4-甲苯二胺与来自不同物种的肝细胞质或仓鼠或家兔的各组织细胞质一起孵化时，选择性地在2,4-甲苯二胺的p-氨基团上发生了N-乙酰化，在o-氨基团上的程度较小。在仓鼠和家兔中，N-乙酰转移酶活性最高的是肝细胞质，其次是肾脏、肠道粘膜上皮和肺。仓鼠肝细胞质的活性最高，其次是豚鼠、家兔、小鼠和大鼠。仅通过人类肝细胞质形成了2,4-甲苯二胺的N-乙酰衍生物的微量。

When 2,4-tolylenediamine was incubated with liver cytosol from various species, or cytosol from various tissues of hamster or rabbit ... n-acetylation occurred selectively at the p-amino group of 2,4-tolylenediamine & to a smaller extent at the o-amino group. In hamsters & rabbits, the highest n-acetyltransferase activity was present in cytosol of liver, followed by that from kidneys, mucosal epithelium of intestine, & lungs. Hamster-liver cytosol had the greatest activity, followed by ... guinea pigs, rabbits, mice & rats. Only a trace of an n-acetyl derivative of 2,4-tolylenediamine was formed thru ... human liver cytosol ... .

来源:Hazardous Substances Data Bank (HSDB)

代谢

2,4-异构体通过肝细胞质中的p-氨基团被选择性地N-乙酰化，该细胞质来自仓鼠、豚鼠、家兔、小鼠和大鼠。研究了来自仓鼠和家兔的肝、肾、肠粘膜和肺的细胞质，使用2,4-DAT和4-乙酰氨基-2-氨基甲苯作为底物进行N-乙酰转移酶活性。所有组织在酶活性上显示出明显的物种差异。具有高N-乙酰转移酶水平的组织，如肝脏，可以产生4-乙酰氨基-2-氨基甲苯和2,4-二乙酰氨基甲苯。肝脏细胞质的N-乙酰化能力也存在性别差异。

... The 2,4-isomer was selectively N-acetylated at the p-amino group by liver cytosol prepared from hamsters, guinea-pigs, rabbits, mice, and rats. The cytosol from liver, kidney, intestinal mucosa, and lung of hamsters and rabbits was studied for N-acetyl transferase activity using 2,4-DAT and 4-acetylamino-2-amino-toluene as substrates. All tissues showed marked species differences in enzyme activity. Tissues with high N-acetyl transferase levels, such as liver, could produce both 4-acetylamino-2-aminotoluene and 2,4- diacetylaminotoluene. There were also sex differences in the N-acetylation capacity of the liver cytosol.

来源:Hazardous Substances Data Bank (HSDB)

代谢

在雄性大鼠中，单次注射2,4-DAT（77 mg/kg体重）后，24小时内以代谢物复合物的形式排出了剂量的69.4%，这表明存在自由和结合衍生物。确定的主要尿液代谢物是4-乙酰氨基-2-氨基甲苯、2,4-二乙酰氨基甲苯和4-乙酰氨基-2-氨基苯甲酸。在小鼠中，甲基氧化成苯甲酸是主要的反应，小鼠的主要尿液代谢物是4-乙酰氨基-2-氨基苯甲酸、4-乙酰氨基-2-氨基甲苯和2,4-二乙酰氨基苯甲酸。

After a single ip injection of 2,4-DAT (77 mg/kg body weight) in male rats, 69.4% of the dose was eliminated in the urine and feces after 24 hr as a complex mixture of metabolites, indicating both free and conjugated derivatives. The major urinary metabolites identified were 4-acetylamino-2-aminotoluene, 2,4- diacetylaminotoluene, and 4-acetylamino-2-aminobenzoic acid. In mice, oxidation of the methyl group to a benzoic acid was the major reaction and the major urinary metabolites in mice were 4- acetylamino-2-aminobenzoic, 4-acetylamino-2-aminotoluene, and 2,4- diacetylaminobenzoic acid.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。有充分的证据表明对动物具有致癌性。总体评估：2B组：该物质可能对人类具有致癌性。

No data are available in humans. Sufficient evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 2B: The agent is possibly carcinogenic to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

2,4-二氨基甲苯：合理预期为人类致癌物。

2,4-Diaminotoluene: reasonably anticipated to be a human carcinogen.

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：2,4-二氨基甲苯

IARC Carcinogenic Agent:2,4-Diaminotoluene

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16卷（1978年）一些芳香胺及其相关硝基化合物 - 染发剂、着色剂和杂项工业化学品

IARC Monographs:Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals

来源:International Agency for Research on Cancer (IARC)

吸收、分配和排泄

当给雄性费舍尔大鼠腹腔注射(14)C-2,4-二氨基甲苯时，血液和血浆中的放射性在1小时达到最大值，并在7小时内迅速下降；5天后，98.6%已被排出（76.5%在尿液中，22.2%在粪便中）。

When (14)C-2,4-diaminotoluene was administered ip to male fisher rats, radioactivity in blood & plasma reached a maximum at 1 hr and decreased rapidly for 7 hr; 98.6% had been excreted after 5 days (76.5% in urine & 22.2% in feces).

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

在活体人类、猴子和小猪中测量了据报道存在于化妆品中的5种物质的皮肤渗透情况。记录的最大皮肤渗透是在猴子腹部皮肤上涂抹2,4-甲苯二胺，而最小的是在猴子腹部、人类腹侧前臂上涂抹2,4-二氨基苯甲醚以及在猴子腹侧前臂上涂抹对二氧杂环烷。... 粗略估计了在适当使用化妆品的条件下，可能通过人类皮肤吸收的量。

Skin penetration by 5 substances that have been reported to be present in cosmetics was measured in vivo in humans, monkeys, and swine. The greatest skin penetration was recorded with 2,4-toluenediamine applied to the abdominal skin of monkeys and the least with 2,4-diaminoanisole on the monkey abdomen and human ventral forearm and with p-dioxane on the monkey ventral forearm. ... Crude estimates were made of the amt that might be absorbed through human skin under appropriate conditions of cosmetics use.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

皮肤渗透研究的结果与实验动物研究的结果相一致。在皮肤接触40分钟后，尿液排泄率在暴露后4到8小时达到最高。在24小时的皮肤接触期间，当测试物质溶于丙酮并涂抹在前臂皮肤上时，2,4-二氨基甲苯的吸收率最高（23.7%）。

The results of skin penetration studies correspond with those from experimental animal studies. After 40 min of dermal contact, the highest rate of urinary excretion occurred 4 - 8 hr after exposure. During 24 hr of dermal contact, the highest absorption of 2,4-diaminotoluene resulted when test material was dissolved in acetone and applied to the skin of the forearm (23.7%).

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

分布因不同物种而异。然而，数据显示，在大多数物种中，浓度最高的器官是肝脏、肾脏和肾上腺。胃肠道也观察到高浓度，而心脏、性腺、大脑和血液中的水平最低。已经证明2,4-异构体与肝脏和肾脏蛋白的绑定是剂量依赖性的。

Distribution varies with different species. However, data indicate that, in most species, the organs with the highest concentrations are the liver, kidneys, and adrenal glands. High concentrations are also observed in the gastrointestinal tract, while the lowest levels are found in the heart, gonads, brain, and blood. A dose-dependent binding of the 2,4-isomer to hepatic and renal proteins has been demonstrated.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1(b)
• 危险品标志：
  T
• 安全说明：
  S45,S53,S61
• 危险类别码：
  R36,R21,R43,R45,R51/53,R25
• WGK Germany：
  3
• 海关编码：
  29331990
• 危险品运输编号：
  UN 1709 6.1/PG 3
• RTECS号：
  XS9625000
• 包装等级：
  III
• 危险类别：
  6.1(b)

制备方法与用途

化学性质
无色针状晶体（由水重结晶）或棱柱状晶体（由乙醇重结晶），易溶于热水、乙醇及乙醚。

用途
用于制取TDI、硫化染料、碱性染料、分散染料及医药中间体，同时也是有机合成的中间体。具体应用包括生产甲苯二异氰酸酯以及染料如毛皮黑DB、硫化黄棕5G、硫化黄棕6G和硫化红棕B3R等。制成的染料能直接使皮毛和头发氧化成黑色。

生产方法
由对硝基甲苯用混酸进行硝化，得到2,4-二硝基甲苯，随后使用铁粉还原得粗品，再经浓缩、蒸馏得成品。原料消耗定额为：对硝基甲苯1600 kg/t、硫酸（98%）1616 kg/t、硝酸（98%）760 kg/t、铁粉（90%）2700 kg/t。

类别
有毒物品
毒性分级
高毒
急性毒性
腹腔-大鼠 LD50: 325 毫克/公斤；腹腔-小鼠 LD50: 480 毫克/公斤
刺激数据
皮肤-兔子 500 毫克/24小时 轻度；眼睛-兔子 100 毫克/24小时 中度
可燃性危险特性
明火可燃，高温分解产生有毒氮氧化物烟雾
储运特性
库房需通风、低温干燥，与氧化剂、食品添加剂及酸类分开存放

灭火剂
泡沫、雾状水、二氧化碳、砂土