Xylidine | 1300-73-8

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Xylidine
• 英文别名: 2,3-dimethylaniline;2,4-dimethylaniline;2,5-dimethylaniline;2,6-dimethylaniline;3,4-dimethylaniline;3,5-dimethylaniline
• CAS: 1300-73-8
• 化学式: C48H66N6
• 分子量: 727.1
• InChiKey: CDULGHZNHURECF-UHFFFAOYSA-N

物化性质

• 熔点：
  -36°C
• 沸点：
  bp 213-226°
• 密度：
  0,98 g/cm3
• 闪点：
  97°C
• 介电常数：
  4.4（20℃）
• 物理描述：
  Xylidines is a pale-yellow to brown liquid with a weak, aromatic, amine-like odor. (NIOSH, 2016)
• 颜色/状态：
  All /isomers/ except ortho-4-xylidine are liquids above 20 °C.
• 气味：
  Weak aromatic amine odor
• 溶解度：
  Slight (NIOSH, 2016)
• 蒸汽密度：
  4.17 (air= 1 at boiling point of xylidine)
• 蒸汽压力：
  Vapor pressure, Pa at 20 °C:
• 稳定性/保质期：

  如果按照规格使用和储存，则不会分解，没有已知危险反应。请避免与氧化物接触。

• 自燃温度：
  520-590 °C
• 腐蚀性：
  Liquid xylidine will attack some forms of plastics, rubber, and coatings.
• 电离电位：
  7.65eV (2,4-) 7.30eV (2,6-)
• 气味阈值：
  Odor Threshold Low: 0.005 [mmHg]; Odor threshold from CHEMINFO

计算性质

• 辛醇/水分配系数(LogP)：
  11.31
• 重原子数：
  54
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  6

ADMET

代谢

关于2,6-二甲氨基苯在人体中的代谢证据来源于对吸烟者和非吸烟者的研究，以及对接受局部麻醉和心脏药物利多卡因治疗的病人的研究。已知利多卡因主要代谢为2,6-二甲氨基苯。利用毛细管气相色谱-质谱技术，发现非吸烟者血红蛋白中2,6-二甲氨基苯的加合物含量很高，尽管他们没有已知的接触这种化合物的经历；此外，吸烟者的加合物水平明显较低。相比之下，接受利多卡因治疗的病人的2,6-二甲氨基苯-血红蛋白加合物水平显著升高。这些结果表明，环境和医源性接触2,6-二甲氨基苯的情况，以及它转化为循环中的N-羟基-2,6-二甲氨基苯代谢物，在人类中进入红细胞，被氧化为2,6-二甲基硝基苯，并与血红蛋白形成亚磺酰胺加合物。/2,6-二甲氨基苯/

Evidence for the metabolism of 2,6-dimethylaniline in humans is derived from studies on cigarette smokers and nonsmokers and on patients receiving the anesthetic and cardiac drug, lidocaine, which is known to be metabolized principally to 2,6-dimethylaniline. Using capillary gas chromatography-mass spectrometry, hemoglobin adducts of 2,6-dimethylaniline were found to be present at high levels in nonsmokers with no known exposure to this compound; moreover, adduct levels were appreciably lower in cigarette smokers. In contrast, 2,6-dimethylaniline-hemoglobin adduct levels were elevated substantially in patients receiving lidocaine treatment. These results are indicative of environmental and iatrogenic exposure to 2,6-dimethylaniline, and of its biotransformation to a circulating N-hydroxy-2,6-dimethylaniline, and of its biotransformation to a circulating N-hydroxy-2,6-dimethylaniline metabolite in humans, which enters erythrocytes, is oxidized to 2,6-dimethyl-nitrosobenzene and forms a sulfinamide adduct with hemoglobin. /2,6-Xylidine/

来源:Hazardous Substances Data Bank (HSDB)

代谢

根据在大鼠中确定的血红蛋白结合指数，非吸烟者中发现的2,6-二甲苯基血红蛋白加合物水平相当于估计的每日暴露量为23微克。2,6-二甲苯基也被发现是另外两种药物，即乙基卡因和盐酸利达米丁的人类尿液代谢物。/2,6-二甲苯基/

On the basis of the hemoglobin binding index determined in rats, the levels of 2,6-dimethylaniline-hemoglobin adducts found in nonsmokers corresponding to an estimated daily exposure of 23 ug. 2,6-Dimethylaniline has also been found as a human urinary metabolite of two other drugs, etidocaine and lidamidine hydrochloride. /2,6-Xylidine/

来源:Hazardous Substances Data Bank (HSDB)

代谢

由于肠道微生物可能将基于2,6-二甲苯胺的偶氮染料代谢成自由的2,6-二甲苯胺，因此研究了从小肠吸收进入血液循环的情况。将10毫克2,6-二甲苯胺（“纯品”）溶解在10毫升pH为6的磷酸盐缓冲盐水中，注入到雄性Wistar大鼠的小肠中。由于吸收半衰期很短（14.4分钟），预计肠道微生物对偶氮染料的代谢将导致产生的2,6-二甲苯胺被身体完全吸收。/2,6-二甲苯胺/

Since free 2,6-dimethylaniline may be formed by intestinal metabolism of 2,6-dimethylaniline-based azo dyes, its absorption into the circulation from the small intestine was studied. Male Wistar rats were instilled with 10 mg 2,6-dimethylaniline ('pure') in 10 ml phosphate-buffered saline pH 6 into the intestine. Since the absorption half-time was rapid (14.4 min), metabolism of azo dyes by intestinal microflora would be expected to result in complete absorption of the resulting 2,6-dimethylaniline by the body. /2,6-Xylidine/

来源:Hazardous Substances Data Bank (HSDB)

代谢

2,6-二甲基苯胺的代谢在给予 Osborne Mendel 雄性大鼠氢氯酸盐（纯度未指定）的水溶液经灌胃给药，剂量为200 mg/kg体重时进行了定性研究。4-羟基-2,6-二甲基苯胺和3-甲基-2-氨基苯甲酸分别被鉴定为主要和次要的尿液代谢物。未改变的胺可以通过色谱法检测到，但仅在酸性尿液水解后，这表明尿液中存在N-结合物。这些数据通过在给予2,6-二甲基苯胺（纯度大于99%）的玉米油溶液经灌胃给药，每日剂量为262.5 mg/kg体重的雄性Fischer 344大鼠中进行酶水解得到了证实。用3-甲基胆蒽预处理后，4-羟基代谢物的水平进一步增加，但用苯巴比妥预处理则没有增加。对雄性比格犬口服给药（每日25 mg/kg体重，连续10天）得到了相同的 主要代谢物；3-甲基-2-氨基苯甲酸及其甘氨酸结合物是尿液中的次要成分。还提供了存在两种潜在反应性代谢物的证据，即2,6-二甲基-4-硝基苯，可能来源于N-羟基-2,6-二甲基苯胺，以及2,6-或3,5-二甲基-4-亚胺喹啉，这两种物质在大鼠中均未被检测到。/2,6-二甲苯胺/

The metabolism of 2,6-dimethylaniline was examined qualitatively in male Osborne Mendel rats given the hydrochloride salt [purity unspecified] by gavage in water at 200 mg/kg bw. 4-Hydroxy-2,6-dimethylaniline and 3-methyl-2-aminobenzoic acid were identified as major and minor urinary metabolites, respectively. The unchanged amine could be detected chromatographically, but only after acidic urine hydrolysis, suggesting the presence of urinary N-conjugates. These data were confirmed by enzymatic hydrolysis in male Fischer 344 rats given 2,6-dimethylaniline ( > 99% pure) by gavage in corn oil at a daily dose of 262.5 mg/kg bw for 10 days. Levels of the 4-hydroxy metabolite were further increased by pretreatment with 3-methylcholanthrene, but not by pretreatment with phenobarbital. Oral administration to male beagle dogs (25 mg/kg bw per day for 10 days) resulted in the same major metabolite; 3-methyl-2-aminobenzoic acid and its glycine conjugate were minor components in the urine. Evidence was also provided for the presence of two potentially reactive metabolites, 2,6-dimethyl-4-nitrosobenzene, which may arise from N-hydroxy-2,6-dimethylaniline, and 2,6- or 3,5-dimethyl-4-iminoquinone, neither of which was detectable in rats. /2,6-Xylidine/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

评估：对于2,6-二甲基苯胺在人类中的致癌性，目前证据不足。在实验动物中，对于2,6-二甲基苯胺的致癌性有足够的证据。总体评估：2,6-二甲基苯胺可能对人类具有致癌性（2B组）。/2,6-二甲苯胺/

Evaluation: There is inadequate evidence in humans for the carcinogenicity of 2,6-dimethylaniline. There is sufficient evidence in experimental animals for the carcinogenicity of 2,6-dimethylaniline. Overall evaluation: 2,6-dimethylaniline is possibly carcinogenic to humans (Group 2B). /2,6-Xylidine/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

A3；已确认对动物有致癌性，但对人类的相关性未知。/莰烯（混合异构体）/

A3; Confirmed animal carcinogen with unknown relevance to humans. /Xylidine (mixed isomers)/

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 暴露途径

该物质可以通过吸入、皮肤接触和摄入被身体吸收，达到危险数量。

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

来源:ILO International Chemical Safety Cards (ICSC)

毒理性

• 暴露途径

吸入，皮肤吸收，吞食，皮肤和/或眼睛接触

inhalation, skin absorption, ingestion, skin and/or eye contact

来源:The National Institute for Occupational Safety and Health (NIOSH)

毒理性

• 症状

缺氧、发绀、高铁血红蛋白血症；肺、肝、肾损伤

Anoxia, cyanosis, methemoglobinemia; lung, liver, kidney damage

来源:The National Institute for Occupational Safety and Health (NIOSH)

安全信息

• 职业暴露等级：
  B
• 职业暴露限值：
  TWA: 2 ppm (10 mg/m3) [skin]
• 危险等级：
  6.1(a)
• 立即威胁生命和健康浓度：
  50 ppm
• 安全说明：
  S28,S36/37,S45
• 危险类别码：
  R23/24/25,R33,R51/53
• RTECS号：
  ZE8575000
• 海关编码：
  2921492000
• 包装等级：
  II
• 危险类别：
  6.1(a)

制备方法与用途

类别：有毒物品

毒性分级：中毒

急性毒性（口服 - 大鼠）：LD₅₀ 610 毫克/公斤

爆炸物危险特性：与空气混合可爆

可燃性危险特性：明火可燃；与氧化剂起作用；受热分解产生有毒氮氧化物烟雾

储运特性：应存放在库房通风、低温和干燥的环境中，并与其他酸类、氧化剂及食品添加剂分开存放

灭火剂：可用泡沫、二氧化碳、干粉或砂土进行扑灭

职业标准：

• TLV-TWA：5 PPM（25 毫克/立方米）
• STEL：20 毫克/立方米

表征谱图