2,6-二溴-3,4-二甲苯酚 | 22802-40-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2,6-二溴-3,4-二甲苯酚
• 英文名称: 2,6-dibromo-3,4-dimethylphenol
• 英文别名: 2,6-dibromo-3-methyl-4-cresol；2,6-dibromo-3,4-dimethyl-phenol；3.5-Dibrom-4-oxy-1.2-dimethyl-benzol；2,6-Dibrom-3,4-dimethyl-phenol；2.6-Dibrom-asymm.-o-xylenol；2,6-dibromo-3,4-xylenol
• CAS: 22802-40-0
• 化学式: C₈H₈Br₂O
• 分子量: 279.959
• InChiKey: KIVOOVZNPGTYDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2908199090

反应信息

• 作为反应物：
  描述：

  2,6-二溴-3,4-二甲苯酚 在 氧气 、 cobalt(II) diacetate tetrahydrate 、 sodium hydroxide 作用下， 以 乙二醇 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以86%的产率得到3,5-dibromo-4-hydroxy-2-methylbenzaldehyde
  参考文献：
  名称：

  EWG取代的4-甲酚的高效Co（OAc）2催化需氧氧化，以获取4-羟基苯甲醛

  摘要：

  我们报告了一种高效的无配体Co（OAc）2 ·4H 2 O / NaOH / O 2 /乙二醇反应系统，该系统能够对包括2,6-di-EWG-，2,3在内的多种底物进行选择性好氧氧化，6-tri-EWG-，2-EWG-和2-EWG-6-EDG取代的4-甲酚变成相应的4-羟基苯甲醛。基于实验研究和明确定义的对苯醌甲基化物，提出了合理的反应机理。考虑到程序的简便性和产品的重要性，该方法有望成为相关的苄基C（sp 3）–H官能化化学中的一种有利且实用的工具。

  DOI：

  10.1016/j.tetlet.2013.12.077
• 作为产物：
  描述：

  3,4-二甲基苯酚 在 benzyltrimethylammonium tribromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以96%的产率得到2,6-二溴-3,4-二甲苯酚
  参考文献：
  名称：

  使用季铵多卤化物的卤化。XX。苯酚与聚合物结合的苄基三甲基三溴化铵的溴化

  摘要：

  通过将苯酚在二氯甲烷 - 甲醇中的溶液通过装有苯乙烯聚合物结合的苄基三甲基三溴化铵的柱子，定量获得溴取代的苯酚。

  DOI：

  10.1246/bcsj.62.3373

文献信息

• Halogenation Using Quaternary Ammonium Polyhalides. XX. Bromination of Phenols with Polymer-Bound Benzyltrimethylammonium Tribromide
  作者：Takaaki Kakinami、Hiroyuki Suenaga、Tadashi Yamaguchi、Tsuyoshi Okamoto、Shoji Kajigaeshi

  DOI：10.1246/bcsj.62.3373

  日期：1989.10

  Bromo-substituted phenols were obtained quantitatively by passing a solution of phenols in dichloromethane–methanol through a column packed with styrene polymer-bound benzyltrimethylammonium tribromide.

  通过将苯酚在二氯甲烷 - 甲醇中的溶液通过装有苯乙烯聚合物结合的苄基三甲基三溴化铵的柱子，定量获得溴取代的苯酚。
• Halogenation Using Quaternary Ammonium Polyhalides. IV. Selective Bromination of Phenols by Use of Tetraalkylammonium Tribromides
  作者：Shoji Kajigaeshi、Takaaki Kakinami、Tsuyoshi Okamoto、Hiroko Nakamura、Masahiro Fujikawa

  DOI：10.1246/bcsj.60.4187

  日期：1987.11

  Reaction of phenols with calculated amounts of benzyltrimethylammonium tribromide or tetrabutylammonium tribromide in dichloromethane–methanol for 0.5–1 h under mild conditions gave, selectively, the objective mono-, di-, or tribromophenols in good yields.

  苯酚与计算量的苄基三甲基三溴化铵或四丁基三溴化铵在温和条件下反应 0.5-1 小时，选择性地以良好的产率得到目标单、二或三溴酚。
• Fischer, Alfred; Henderson, George Narayanan, Canadian Journal of Chemistry, 1983, vol. 61, p. 1045 - 1052
  作者：Fischer, Alfred、Henderson, George Narayanan

  DOI：——

  日期：——
• Understanding Solid/Solid Organic Reactions
  作者：Gadi Rothenberg、Andrew P. Downie、Colin L. Raston、Janet L. Scott

  DOI：10.1021/ja0034388

  日期：2001.9.1

  The concept of an organic reaction between two macroscopic solid particles is investigated. Thus, we study several reactions that have been recently reported to proceed "in the solid phase" and clearly show that, in most cases, grinding the two solid reactants together results in the formation of a liquid phase. This is true both for catalytic transformations (e.g., aldol condensations and oligomerization of benzylic compounds) and for noncatalytic reactions (Baeyer-Villiger oxidations, oxidative coupling of naphthols using iron chloride, condensation of amines and aldehydes to form azomethines, homo-etherification of benzylic alcohols using p-toluenesulfonic acid, and nuclear aromatic bromination with NBS). This liquefaction implies the existence of a eutectic mixture with T-fusion below ambient temperature (although both reagents have higher than ambient melting points). In cases where heating is required, it is again clear that a phase change (from solid to liquid) occurs, explaining the observed reaction kinetics. On the basis of 19 experimental examples, we discuss the possibility of solid-phase organic reactions and the implications of these findings to the reaction between two solid reagents. A general description of such reactive systems is proposed. based on a consideration of the potential for eutectic (or peritectic) formation between the constituents of the liquid phases that arise during the process of mechanical mixing of the solid reagents and products.
• Auwers, Justus Liebigs Annalen der Chemie, 1906, vol. 344, p. 179
  作者：Auwers

  DOI：——

  日期：——