2,4,6-trinitrophenyl chloroformate | 34900-21-5

• 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: 2,4,6-trinitrophenyl chloroformate
• 英文别名: Pikryl-chloroformat；Picrylchloroformat；(2,4,6-Trinitrophenyl) carbonochloridate
• CAS: 34900-21-5
• 化学式: C₇H₂ClN₃O₈
• 分子量: 291.561
• InChiKey: BYTMTEBIDYJJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  164
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  光气 、 苦味酸 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以83%的产率得到2,4,6-trinitrophenyl chloroformate
  参考文献：
  名称：

  A Safe and Efficient Route for the Preparation of Nitro-, Dinitro-, and Trinitrophenyl Chloroformates

  摘要：

  A safe and simple method has been developed for synthesis of chloroformates derived from 2-nitrophenol, 4-nitrophenol, 2,4-dinitrophenol, 2,4,6-trinitrophenol, and pentafluorophenol, the yields being in the range of 72-96%. The method is based on a heterogeneous reaction of the substituted phenol with phosgene dissolved in dichloromethane catalyzed with solid anhydrous potassium carbonate. The synthesis of 2,4,6-trinitrophenyl chloroformate takes place only in the presence of a phase-transfer catalyst, in this case the easily recovered ,-dimethoxy poly(ethylene glycol) (PEG; M=2kDa). The only waste products of the suggested synthesis of the mentioned esters are sodium chloride and potassium chloride. The method markedly reduces the explosion risk connected with drying and handling of salts of mono-, di-, and trinitrophenols and is much more environmentally friendly than the currently used methods. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.709300

文献信息

• JPS62252800A
  申请人：——

  公开号：JPS62252800A

  公开（公告）日：1987-11-04
• US3742011A
  申请人：——

  公开号：US3742011A

  公开（公告）日：1973-06-26
• A Safe and Efficient Route for the Preparation of Nitro-, Dinitro-, and Trinitrophenyl Chloroformates
  作者：Miloš Sedlák、Vladimír Pejchal、Aleš Imramovský、Jiří Hanusek

  DOI：10.1080/00397911.2012.709300

  日期：2013.9.2

  A safe and simple method has been developed for synthesis of chloroformates derived from 2-nitrophenol, 4-nitrophenol, 2,4-dinitrophenol, 2,4,6-trinitrophenol, and pentafluorophenol, the yields being in the range of 72-96%. The method is based on a heterogeneous reaction of the substituted phenol with phosgene dissolved in dichloromethane catalyzed with solid anhydrous potassium carbonate. The synthesis of 2,4,6-trinitrophenyl chloroformate takes place only in the presence of a phase-transfer catalyst, in this case the easily recovered ,-dimethoxy poly(ethylene glycol) (PEG; M=2kDa). The only waste products of the suggested synthesis of the mentioned esters are sodium chloride and potassium chloride. The method markedly reduces the explosion risk connected with drying and handling of salts of mono-, di-, and trinitrophenols and is much more environmentally friendly than the currently used methods. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.