1-(2-甲基苯基)偶氮萘-2-胺 | 131-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(2-甲基苯基)偶氮萘-2-胺
• 中文别名: 1-(2-o-苯甲基偶氮)-2-萘基胺；邻甲苯偶氮-2-萘胺；油黄OB
• 英文名称: 1-[(2-methylphenyl)azo]naphthalen-2-amine
• 英文别名: α-(o-tolylazo)-β-naphthylamine；1-(2'-methylbenzeneazo)-2-amino-naphthalene；α-(o-tolylazo)-2-naphthylamine；o-(2-amino-1-naphthylazo)toluene；Yellow OB；1-o-tolylazo-[2]naphthylamine；1-[(2-methylphenyl)diazenyl]naphthalen-2-amine
• CAS: 131-79-3
• 化学式: C₁₇H₁₅N₃
• mdl: MFCD00046381
• 分子量: 261.326
• InChiKey: BWLVSYUUKOQICP-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126° (Fischer)
• 沸点：
  394.58°C (rough estimate)
• 密度：
  1.1394 (rough estimate)
• 颜色/状态：
  Deep red crystals from alcohol. Also reported as bright yellow needles
• 溶解度：
  In water, 8.30X10-2 mg/L at 25 °C (est)
• 蒸汽压力：
  1.95X10-7 mm Hg at 25 °C (est)
• 分解：
  When heated to decomposition it emits toxic fumes of /nitrogen oxide/.

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.058
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

代谢

黄色OB通过与大鼠和家兔胃中的醛类反应转化为咪唑衍生物。

Yellow OB is converted to an imidazole derivative by reaction with aldehydes in the stomachs of rats and rabbits.

来源:Hazardous Substances Data Bank (HSDB)

代谢

1-(邻-甲苯基偶氮)-6-羟基-2-磺胺基萘-O-葡萄糖苷酸和1-(邻-甲苯基偶氮)-2-磺胺基萘也出现在大鼠和兔的尿液中。

1-(ortho-Tolylazo)-6-hydroxy-2-sulphonaminonaphthalene-O-glucuronide and 1(ortho-toylazo)-2-sulphonaminonaphthalene were also present in the urine of /rats and rabbits/.

来源:Hazardous Substances Data Bank (HSDB)

代谢

胆汁中含有1-(邻甲苯偶氮)-6-羟基-2-萘基胺-O-氢硫酸盐N-葡萄糖苷酸酯，1-(邻甲苯偶氮)-6-羟基-2-磺酰胺基萘-O-葡萄糖苷酸酯，1-(邻甲苯偶氮)-6-羟基-2-萘基胺-N-葡萄糖苷酸酯和1-(邻甲苯偶氮)-2-磺酰胺基萘。

Bile contained 1-(ortho-tolylazo)-6-hydroxy-2-naphthylamine-O-hydrogen sulfate N-glucuronide, 1-(ortho-tolylazo)-6-hydroxy-2-susulphonamino-naphthalene-O-glucuronide, 1-(ortho-tolylazo)-6-hydroxy-2-naphthylamine-N-glucuronide and 1-(ortho-tolylazo)-2-sulphonaminonaphtalene.

来源:Hazardous Substances Data Bank (HSDB)

代谢

作为研究肠道菌群参与食品添加剂代谢的一部分，比较了肠道细菌和肝脏微粒体的偶氮和硝基还原酶系统的某些特性。细菌还原酶是通过超声波破裂从大肠杆菌的冻干细胞中制备的。发现大多数需要FMN和NADP的偶氮和硝基还原酶活性在...（雄性哈特利豚鼠）肝脏微粒体中，在水溶性磺化偶氮染料和p-硝基苯甲酸的还原中。然而，脂溶性偶氮染料，如油黄AB和OB，并没有被任一酶系统还原。观察到两种酶系统对偶氮染料底物特异性的一些差异，并且CO、KCN、O2和螯合剂对抑制效果的影响有显著差异。

As a part of studies on the participation of intestinal flora in the metabolism of food additives, some properites of azo- and nitro-reductase systems of intestinal bacteria and liver microsomes were compared. The bacterial reductase was prepared from the lyophilized cells of Escherichia coli by ultrasonic disruption. Most of azo- and nitro-reductase activity which required FMN and NADP was found in the ... (male Hartley guinea pig) liver microsomes in the reduction of water-soluble sulfonated azo dyes and p-nitrobenzoic acid. However, fat-soluble azo dyes, such as Oil Yellow AB and OB, were not reduced by either of the enzyme systems. Some difference in the substrate specificity for azo dyes was observed between the 2 enzyme systems and there was a remarkable difference in the inhibitory effect by CO, KCN, O2 and chelating agents.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性证据不足。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

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：黄色氧化铍

IARC Carcinogenic Agent:Yellow OB

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：第3组：对其对人类的致癌性无法分类

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity 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8卷（1975年）一些芳香偶氮化合物

IARC Monographs:Volume 8: (1975) Some Aromatic Azo Compounds

来源:International Agency for Research on Cancer (IARC)

毒理性

• 解毒与急救

/SRP:/ 立即急救：确保已经进行了充分的中毒物清除。如果患者停止呼吸，开始人工呼吸，最好使用需求阀复苏器、袋阀面罩装置或口袋面罩，按训练进行操作。如有必要，进行心肺复苏。立即用缓慢流动的水冲洗受污染的眼睛。不要催吐。如果发生呕吐，让患者前倾或置于左侧（如果可能的话，头部向下）以保持呼吸道畅通，防止吸入性肺炎。保持患者安静，维持正常体温。寻求医疗帮助。 /毒物A和B/

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

使用(14)C标记的颜料研究表明，几乎所有的黄色颜料在48小时内被消除：粪便中含82%，尿液中含18%的放射性。

Studies with (14)C-labelled color indicated that almost all of the yellow OB was eliminated in 48 hours: the feces contained 82% and urine 18% of the radioactivity.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

/Yellow OB/ 在sc注射后在身体的脂肪组织中积累，并缓慢消除...

/Yellow OB/ accumulates in fatty tissues of the body after its sc injection and is eliminated slowly...

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 海关编码：
  2927000090

反应信息

• 作为反应物：
  描述：

  1-(2-甲基苯基)偶氮萘-2-胺 在 双氧水 、 溶剂黄146 作用下， 生成 2-硝基-1-萘酚
  参考文献：
  名称：

  Charrier; Crippa, Gazzetta Chimica Italiana, 1925, vol. 55, p. 23

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基苯胺 盐酸盐 、 naphthalene-2-diazonium chloride 在 水 、 sodium acetate 作用下， 生成 1-(2-甲基苯基)偶氮萘-2-胺
  参考文献：
  名称：

  Norman, Journal of the Chemical Society, 1912, vol. 101, p. 1922,1923

  摘要：

  DOI：

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ni: MVol.C2, 7.21, page 776 - 787
  作者：

  DOI：——

  日期：——
• Kruess, Zeitschrift fur Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre, 1905, vol. 51, p. 290
  作者：Kruess

  DOI：——

  日期：——
• Charrier, G.; Beretta, A., Gazzetta Chimica Italiana, 1926, vol. 56, p. 865 - 871
  作者：Charrier, G.、Beretta, A.

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Cu: MVol.B4, 184, page 1856 - 1859
  作者：

  DOI：——

  日期：——
• Crippa, G. B., Gazzetta Chimica Italiana, 1927, vol. 57, p. 20 - 25
  作者：Crippa, G. B.

  DOI：——

  日期：——