2,3,5,6-tetrabromo-4-nitrophenol | 6161-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3,5,6-tetrabromo-4-nitrophenol
• 英文别名: 2,3,5,6-Tetrabrom-4-nitro-phenol；2,3,5,6-Tetrabrom-4-nitrophenol
• CAS: 6161-55-3
• 化学式: C₆HBr₄NO₃
• 分子量: 454.695
• InChiKey: VLBWGEJJANMXEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 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：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetrabromo-4-nitrophenol 在 盐酸 、 tin 、 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 2,3,5,6-tetrabromo-p-quinone diazide
  参考文献：
  名称：

  多溴醌二叠氮化物的合成及一些转化

  摘要：

  在浓盐酸水溶液中用粒状锡还原多溴邻-和对硝基苯酚，得到多溴氨基苯酚，将其与亚硝酸钠在浓硫酸中于0℃下重氮化，得到多溴对-邻和对醌二叠氮化物。它们通过消除氮而热分解生成酮卡宾，酮卡宾与乙酰丙酮反应形成在活化的亚甲基上的插入产物。由邻醌二叠氮化物生成的酮卡宾与典型的双极性亲和剂如乙腈，苄腈，苯乙烯和苯乙炔反应，得到相应的[3 + 2]-环加成产物。

  DOI：

  10.1134/s1070428017120053
• 作为产物：
  描述：

  3,5-二溴-4-甲氧基苯胺 在 盐酸 、 氢溴酸 、 硝酸 、 tin(ll) chloride 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 15.03h， 生成 2,3,5,6-tetrabromo-4-nitrophenol
  参考文献：
  名称：

  Products of reaction between tetrabromo-substituted ortho- and para-hydroxybenzoic acids and sodium nitrite in CH3COOH

  摘要：

  The reaction of 2,3,5,6-tetrabromo-4-hydroxybenzoic acid with a 10-fold excess of NaNO2 in the glacial acetic acid at 20A degrees C affords tetrabromonitrosophenols whose further transformations under the reaction conditions leads to the formation of a mixture of 2,4,5,6-tetrabromo-p-quinone diazide and tetrabromo-p- and -o-nitrophenols in the molar ratio 37: 2: 1. Under similar conditions the 3,4,5,6-tetrabromo-2-hydroxybenzoic acid is converted into a mixture of 3,4,5,6-tetrabromo-o-quinone diazide with the same nitrophenols in the ratio 13: 1: 3. The reaction of sodium 2,3,5,6-tetrabromo-4-hydroxy-benzoate with NaNO2 in dilute acetic acid resulted in a quantitative yield of tetrabromo-p-quinone monooxime.

  DOI：

  10.1134/s1070428012080064

文献信息

• Displacement of an acetamido- and a nitro-group during bromination of an aromatic compound
  作者：Charles R. Harrison、J. F. W. McOmie

  DOI：10.1039/j39660000997

  日期：——

  Bromination of 4-acetamido-3-nitroanisole has been found to give 2,3,4,5-tetrabromoanisole. Possible mechanisms for this remarkable reaction are suggested.

  发现4-乙酰氨基-3-硝基苯甲醚的溴化得到2,3,4,5-四溴苯甲醚。建议这种显着反应的可能机制。
• METHOD FOR DETERMINING ENZYMATIC ACTIVITY
  申请人：IATRON LABORATORIES, INC.

  公开号：EP0411159B1

  公开（公告）日：1995-11-22
• US5350677A
  申请人：——

  公开号：US5350677A

  公开（公告）日：1994-09-27
• Products of reaction between tetrabromo-substituted ortho- and para-hydroxybenzoic acids and sodium nitrite in CH3COOH
  作者：M. V. Fadin、I. V. Tarasova、V. A. Vasin、V. N. Shishkin

  DOI：10.1134/s1070428012080064

  日期：2012.8

  The reaction of 2,3,5,6-tetrabromo-4-hydroxybenzoic acid with a 10-fold excess of NaNO2 in the glacial acetic acid at 20A degrees C affords tetrabromonitrosophenols whose further transformations under the reaction conditions leads to the formation of a mixture of 2,4,5,6-tetrabromo-p-quinone diazide and tetrabromo-p- and -o-nitrophenols in the molar ratio 37: 2: 1. Under similar conditions the 3,4,5,6-tetrabromo-2-hydroxybenzoic acid is converted into a mixture of 3,4,5,6-tetrabromo-o-quinone diazide with the same nitrophenols in the ratio 13: 1: 3. The reaction of sodium 2,3,5,6-tetrabromo-4-hydroxy-benzoate with NaNO2 in dilute acetic acid resulted in a quantitative yield of tetrabromo-p-quinone monooxime.
• Synthesis and some transformations of polybrominated quinone diazides
  作者：V. A. Vasin、M. V. Fadin、I. V. Tarasova

  DOI：10.1134/s1070428017120053

  日期：2017.12

  The reduction of polybrominated o- and p-nitrophenols with granular tin in concentrated aqueous HCl gave polybrominated aminophenols which were diazotized with sodium nitrite in concentrated sulfuric acid at 0°C to obtain polybrominated o- and p-quinone diazides. Their thermolysis with elimination of nitrogen generated ketocarbenes which reacted with acetylacetone to form insertion products at the

  在浓盐酸水溶液中用粒状锡还原多溴邻-和对硝基苯酚，得到多溴氨基苯酚，将其与亚硝酸钠在浓硫酸中于0℃下重氮化，得到多溴对-邻和对醌二叠氮化物。它们通过消除氮而热分解生成酮卡宾，酮卡宾与乙酰丙酮反应形成在活化的亚甲基上的插入产物。由邻醌二叠氮化物生成的酮卡宾与典型的双极性亲和剂如乙腈，苄腈，苯乙烯和苯乙炔反应，得到相应的[3 + 2]-环加成产物。