2-nitro-3,4,5,6-tetrabromoanisole | 6161-58-6

• 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-nitro-3,4,5,6-tetrabromoanisole
• 英文别名: 3,4,5,6-tetrabromo-2-nitroanisole；2,3,4,5-Tetrabrom-6-nitro-anisol；Tetrabromonitroanisole；1,2,3,4-tetrabromo-5-methoxy-6-nitrobenzene
• CAS: 6161-58-6
• 化学式: C₇H₃Br₄NO₃
• 分子量: 468.722
• InChiKey: LEFNUPLAPVCMIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-nitro-3,4,5,6-tetrabromoanisole 在 三溴化硼 作用下， 生成 2,3,4,5-tetrabromo-6-nitrophenol
  参考文献：
  名称：

  芳香化合物溴化过程中乙酰氨基和硝基的置换

  摘要：

  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。

  DOI：

  10.1039/j39660000997
• 作为产物：
  描述：

  4-甲氧基-2-硝基乙酰苯胺 在 吡啶 、 硫酸 、 溴 、 硝酸 、 溶剂黄146 作用下， 生成 2-nitro-3,4,5,6-tetrabromoanisole
  参考文献：
  名称：

  芳香化合物溴化过程中乙酰氨基和硝基的置换

  摘要：

  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。

  DOI：

  10.1039/j39660000997

文献信息

• 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.
• Regioselectivity of methoxydebromination of substituted pentabromobenzenes C6Br5X in pyridine
  作者：V. N. Shishkin、K. K. Lapin、S. A. Shabarina、K. P. Butin

  DOI：10.1007/bf01151297

  日期：1995.9

  The kinetics and regioselectivity of methoxydebromination of some substituted pentabromobenzenes C(6)Br(5)X (X = NO2, CN, NH2, MeNH, and MeO) were studied in pyridine at 115 degrees C. The partial rate factors (k(f)) were calculated for different positions of the polybrominated ring in these compounds. The effect of substituents X on methoxydebromination at the meta- and para-positions is satisfactorily described only by the Hammett substituent constants (rho = 2.22, r = 0.96). This allows one to conclude that direct polar conjugation of the substituents contributes only slightly to the transition state of the reaction. The ortho-bromine atoms have a significant steric effect.