3,3-二甲氧羰基对二氨基联苯 | 15403-45-9

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 3,3-二甲氧羰基对二氨基联苯
• 中文别名: 33二甲酯基苯并啶
• 英文名称: Dimethyl 4,4'-diamino-3,3'-biphenylylenedicarboxylate
• 英文别名: 3,3'-dicarbomethoxybenzidine；Benzidin-3,3'-dicarbonsaeuredimethylester；methyl 2-amino-5-(4-amino-3-methoxycarbonylphenyl)benzoate
• CAS: 15403-45-9
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: RSSUDYOKPAZOGO-UHFFFAOYSA-N

物化性质

• 熔点：
  201-202 °C
• 沸点：
  478.7±45.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 海关编码：
  2922499990

反应信息

• 作为反应物：
  描述：

  3,3-二甲氧羰基对二氨基联苯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 24.0h， 以24%的产率得到4,4'-二氨基-3,3'-二甲基联苯
  参考文献：
  名称：

  ortho-Substituent effects on the in vitro and in vivo genotoxicity of benzidine derivatives

  摘要：

  Benzidine and its 3,3'-diamino, 3,3'-dimethyl, 3,3'-dimethoxy, 3,3'-difluoro, 3,3'-dichloro, 3,3'-dibromo, 3,3'-dicarbomethoxy and 3,3'-dinitro derivatives together with 2-nitrobenzidine and 3-nitrobenzidine were compared for their in vitro and in vivo genotoxicity. Relative mutagenicity was established with Salmonella strains TA98, TA98/1,8-DNP6 and TA100 with and without S9 activation. All the derivatives in the presence of S9 were more mutagenic than benzidine with 3,3'-dinitro- and 3-nitro-benzidine having the greatest mutagenicity. Mutagenicity in all 3 strains with S9 activation could be correlated to electron-withdrawing ability of substituent groups, as measured by the basicity of the amines. This correlation was explained on the basis that electron-withdrawing groups could favor the stability of the mutagenic intermediate N-hydroxylamine and also enhance the reactivity of the ultimate mutagenic species, the nitrenium ion. Mutagenicity was also correlated to the energy of the lowest unoccupied molecular orbitals (E(LUMO)). Hydrophobicity was found to have very limited effect on the relative mutagenicity of our benzidine derivatives. The in vivo endpoint was chromosomal aberrations in the bone-marrow cells of mice following intraperitoneal administration of benzidine and its derivatives. In contrast to the in vitro results, while all the amines were genotoxic in vivo, only the 3-nitro derivative had a significant increase in toxicity over benzidine.

  DOI：

  10.1016/0165-1218(93)90027-b
• 作为产物：
  描述：

  甲醇 、 4,4-二氨基-1,1-联苯-3,3-二羧酸 在 硫酸 作用下， 反应 48.0h， 以22%的产率得到3,3-二甲氧羰基对二氨基联苯
  参考文献：
  名称：

  ortho-Substituent effects on the in vitro and in vivo genotoxicity of benzidine derivatives

  摘要：

  Benzidine and its 3,3'-diamino, 3,3'-dimethyl, 3,3'-dimethoxy, 3,3'-difluoro, 3,3'-dichloro, 3,3'-dibromo, 3,3'-dicarbomethoxy and 3,3'-dinitro derivatives together with 2-nitrobenzidine and 3-nitrobenzidine were compared for their in vitro and in vivo genotoxicity. Relative mutagenicity was established with Salmonella strains TA98, TA98/1,8-DNP6 and TA100 with and without S9 activation. All the derivatives in the presence of S9 were more mutagenic than benzidine with 3,3'-dinitro- and 3-nitro-benzidine having the greatest mutagenicity. Mutagenicity in all 3 strains with S9 activation could be correlated to electron-withdrawing ability of substituent groups, as measured by the basicity of the amines. This correlation was explained on the basis that electron-withdrawing groups could favor the stability of the mutagenic intermediate N-hydroxylamine and also enhance the reactivity of the ultimate mutagenic species, the nitrenium ion. Mutagenicity was also correlated to the energy of the lowest unoccupied molecular orbitals (E(LUMO)). Hydrophobicity was found to have very limited effect on the relative mutagenicity of our benzidine derivatives. The in vivo endpoint was chromosomal aberrations in the bone-marrow cells of mice following intraperitoneal administration of benzidine and its derivatives. In contrast to the in vitro results, while all the amines were genotoxic in vivo, only the 3-nitro derivative had a significant increase in toxicity over benzidine.

  DOI：

  10.1016/0165-1218(93)90027-b

文献信息

• Disazo pigment composition and printing ink
  申请人：DAINIPPON INK AND CHEMICALS, INC.

  公开号：EP0823459A2

  公开（公告）日：1998-02-11

  A disazo pigment composition, capable of being used to form inks or coatings having both high flow ability and high viscosity, containing (a) a disazo pigment, (b) an asymmetrical disazo compound having a water-soluble group and (c) an asymmetrical disazo compound, which has a substituent group possessing a hydrogen-bonding property.

  一种二氮杂颜料组合物，可用于配制具有高流动性和高粘度的油墨或涂料，该组合物包含 (a) 一种二氮杂颜料，(b) 一种具有水溶性基团的不对称二氮杂化合物，以及 (c) 一种不对称二氮杂化合物，该化合物具有一个具有氢键特性的取代基团。
• Garin, Javier; Melendez, Enrique; Merchan, Francisco L., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1351 - 1354
  作者：Garin, Javier、Melendez, Enrique、Merchan, Francisco L.、Merino, Pedro、Orduna, Jesus、et al.

  DOI：——

  日期：——
• US4053464A
  申请人：——

  公开号：US4053464A

  公开（公告）日：1977-10-11
• US4122117A
  申请人：——

  公开号：US4122117A

  公开（公告）日：1978-10-24
• US5493011A
  申请人：——

  公开号：US5493011A

  公开（公告）日：1996-02-20