3,6-dichloro-benzene-1,2,4,5-tetracarbonitrile | 3533-08-2

• 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: 3,6-dichloro-benzene-1,2,4,5-tetracarbonitrile
• 英文别名: 3,6-Dichlorobenzene-1,2,4,5-tetracarbonitrile
• CAS: 3533-08-2
• 化学式: C₁₀Cl₂N₄
• 分子量: 247.043
• InChiKey: KFBDYHUYOSVNFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 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：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,6-dichloro-benzene-1,2,4,5-tetracarbonitrile 以26%的产率得到
  参考文献：
  名称：

  BUCSIS L.; FRIEDRICH K., CHEM. BER. , 1976, 109, NO 7, 2469-2474

  摘要：

  DOI：
• 作为产物：
  描述：

  4-chloro-2,3,5,6-tetracyanophenol 在 吡啶 、 三氯氧磷 作用下， 反应 0.12h， 以0.8 mg的产率得到3,6-dichloro-benzene-1,2,4,5-tetracarbonitrile
  参考文献：
  名称：

  Successive Photosubstitution of Hexachlorobenzene with Cyanide Ion

  摘要：

  We report a novel nucleophilic polysubstitution reaction of hexachlorobenzene (HCB) with cyanide ion in acetonitrile/water. Successive photocyanations of HCB occur with high quantum yield (phi(diss) --> 0.18) without the need for an electron acceptor, to give as products pentacyanophenol, 4-chloro-2,3,5,6-tetracyanophenol, and a dichlorotricyanophenol. The phenol functional group is introduced by competing hydrolysis of the polycyanochlorinated benzenes. Sensitization and quenching experiments indicate a triplet reactive excited state. Variation of [CN-] at constant [HCB] follows the expected relationship phi(diss) -1 proportional to [CN-](-1), but variation of [HCB] at constant [CN-] shows that the reaction becomes less efficient with increasing [HCB], consistent with the formation of an unproductive excimer.

  DOI：

  10.1021/ja980403n

文献信息

• Method for production of nuclear halogenated aromatic compound possessing cyano groups
  申请人：NIPPON SHOKUBAI CO., LTD.

  公开号：EP0795541A1

  公开（公告）日：1997-09-17

  A nuclear halogenated aromatic compound possessing cyano groups is produced by a method using as a raw material an aromatic compound which possesses cyano groups and assumes a solid state at room temperature and subjecting the raw material to a procedure comprising a step of melting and transporting the compound by a means transport-melting, a step of vaporizing the compound, a step of mixing the compound with a halogen gas, and a step of causing the vapor of the compound to react with the halogen gas in vapor phase in the presence of a catalyst sequentially in the order mentioned, which comprises maintaining a content of a self-condensate of the aromatic compound possessing cyano groups which arise during the melting of the aromatic compound possessing cyano groups in a gas of the compound which reacts with the halogen gas to a level of not more than 2.5 mol% based on the compound. The catalyst used in the method is activated carbon such that the average pore radius thereof determined by the nitrogen adsorption method is not less than 12.2 Å and the cumulative pore volume of the portion of the activated carbon having pore radiuses in the range of 5 - 100 Å determined by the steam adsorption method is not less than 0.45 g/cc.

  一种具有氰基的核卤化芳香族化合物的制备方法是，以一种具有氰基并在室温下呈固态的芳香族化合物为原料，将该原料置于一个程序中，该程序包括用一种运输-熔化方法熔化和运输该化合物的步骤、使该化合物气化的步骤、使该化合物与卤素气体混合的步骤，以及使该化合物的蒸气在有催化剂存在的情况下按上述顺序与气相中的卤素气体反应的步骤、在催化剂存在下，使化合物蒸气在气相中与卤素气体按上述顺序依次反应的步骤，该步骤包括将与卤素气体反应的化合物气体中具有氰基的芳香族化合物在熔化过程中产生的具有氰基的芳香族化合物自缩合物的含量保持在不超过化合物总量的 2.5 mol%。本发明方法中使用的催化剂是活性炭，其平均孔半径用氮吸附法测定不小于 12.2 Å，孔半径在 5 - 100 Å范围内的活性炭部分的累积孔体积用蒸汽吸附法测定不小于 0.45 g/cc。
• Tetracyano-p-phenylenediamine
  作者：O. W. Webster、M. Brown、R. E. Benson

  DOI：10.1021/jo01020a535

  日期：1965.9
• BUCSIS L.; FRIEDRICH K., CHEM. BER. <CHBE-AM>, 1976, 109, NO 7, 2462-2468
  作者：BUCSIS L.、 FRIEDRICH K.

  DOI：——

  日期：——
• Bucsis,L.; Friedrich,K., Chemische Berichte, 1976, vol. 109, p. 2469 - 2474
  作者：Bucsis,L.、Friedrich,K.

  DOI：——

  日期：——
• US5789582A
  申请人：——

  公开号：US5789582A

  公开（公告）日：1998-08-04