2,3,5,6-tetrabromoanisole | 95970-18-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,3,5,6-tetrabromoanisole
• 英文别名: 1,2,4,5-tetrabromo-3-methoxybenzene
• CAS: 95970-18-6
• 化学式: C₇H₄Br₄O
• 分子量: 423.724
• InChiKey: QZSVLKRVOCTXIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  12
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetrabromoanisole 在 正丁基锂 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.5h， 生成 1-methoxy-3,5-bis[2,6-diisopropyl-4-(2-methoxyphenyl)phenyl]-2,6-bis(dicyclohexylphosphino)-benzene
  参考文献：
  名称：

  联芳基二膦配体及其过渡金属络合物

  摘要：

  本发明联芳基二膦配体及其过渡金属络合物提供一个配体分子中带有双膦基但不能螯合配位到一个金属原子中心的联苯膦配体和它们的制备方法。本发明还提供它们配位的过渡金属络合物和用途，特别是它们配位的钯络合物在催化（拟）卤代芳烃为底物之一的偶联反应中的用途。

  公开号：

  CN115385956A
• 作为产物：
  描述：

  3,5-二溴-4-甲氧基苯胺 在 盐酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 15.0h， 生成 2,3,5,6-tetrabromoanisole
  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

• Regioselectivity of reductive debromination of substituted pentabromobenzenes with sodium tert-butoxide in DMSO
  作者：V. N. Shishkin、I. V. Tarasova、K. P. Butin

  DOI：10.1007/s11172-006-0126-1

  日期：2005.10

  The regioselectivity of reductive debromination of substituted pentabromobenzenes C6Br5X (X = NH2, OMe, Me, H, Cl, F, and NO2) under the action of ButONa in DMSO containing ButOH has been studied. The reaction followed the halophilic mechanism via carbanions.

  研究了在含有 ButOH 的 DMSO 中，在 ButONa 的作用下，取代的五溴苯 C6Br5X（X = NH2、OMe、Me、H、Cl、F 和 NO2）还原脱溴的区域选择性。该反应通过碳负离子遵循嗜盐机制。
• 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。
• 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.
• Shishkin, V. N.; Lapin, K. K.; Tanaseichuk, B. S., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 3, p. 516 - 522
  作者：Shishkin, V. N.、Lapin, K. K.、Tanaseichuk, B. S.、Butin, K. P.

  DOI：——

  日期：——
• Shishkin, V. N.; Tanaseichuk, B. S.; Lapin, K. K., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2357 - 2366
  作者：Shishkin, V. N.、Tanaseichuk, B. S.、Lapin, K. K.、Ivkina, A. A.、Butin, K. P.

  DOI：——

  日期：——