2,4-二溴-3,6-二甲基苯胺 | 26829-89-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4-二溴-3,6-二甲基苯胺
• 中文别名: 2,3-己二酮
• 英文名称: 2,4-dibromo-3,6-dimethylaniline
• 英文别名: 2,4-dibromo-3,6-dimethyl-aniline；2,4-Dibrom-3,6-dimethyl-anilin；3.5-Dibrom-2-amino-p-xylol；4,6-Dibromo-2,5-dimethylanilin；2,4-Dibrom-3,6-dimethylanilin
• CAS: 26829-89-0
• 化学式: C₈H₉Br₂N
• 分子量: 278.974
• InChiKey: NNARIZVVHGNNHI-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  296.0±35.0 °C(Predicted)
• 密度：
  1.781±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2921430090

反应信息

• 作为反应物：
  描述：

  2,4-二溴-3,6-二甲基苯胺 在 硫酸 、 sodium nitrite 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 4.0h， 生成 3-bromo-2,5-dimethylbenzonitrile
  参考文献：
  名称：

  Synthesis, Reactions, and Structural and NMR Features of [2.2]Metacyclophane Monoenes and Their Tricarbonylchromium and Cyclopentadienyliron(+) Complexes

  摘要：

  8,16-Dimethyl-, 5,8,13,16-tetramethyl, and 4,6,8,12,14,16-hexamethyl[2,2]metacyclophanene have been synthesized from the corresponding methyl-substituted 3-thia[3.2]metacyclophane precursors via a Wittig rearrangement-Hofmann elimination procedure. Simple addition of bromine or similar electrophiles to the bridge double bond of the cyclophane monoenes did not occur; rather, the methyl-substituted dihydropyrenes were formed. However, mono- and bis-tricarbonylchromium and monocyclopentadienyliron complexes were obtained using ligand-exchange reactions. Addition of bromine to the cyclophane bridge double bond of the iron complex did occur, but unusually slowly. Surprisingly, debromination rather than dehydrobromination occurred when the dibromo addition product was treated with a variety of bases. Photoisomerization of the monoenes and nucleophilic substitution of the metal complexes was also investigated. The geometries of the monoenes and their complexes were compared to the cyclophanes and the cyclophanedienes and to the monothia- and dithiacyclophanes, by comparison of X-ray and calculated structural data and NMR spectroscopic data. Introduction of double bonds into the cyclophane bridges causes the cyclophane step to be less steep but increases distortion of the internal atoms out of the plane of the benzene rings. Making the bridges nonidentical also causes a sideways twist of the step.

  DOI：

  10.1021/jo990721k
• 作为产物：
  描述：

  2,5-二甲基乙酰苯胺 在 溴 、 溶剂黄146 作用下， 生成 2,4-二溴-3,6-二甲基苯胺
  参考文献：
  名称：

  Jaeger; Blanksma, Recueil des Travaux Chimiques des Pays-Bas, 1906, vol. 25, p. 362

  摘要：

  DOI：

文献信息

• Halogenation Using Quaternary Ammonium Polyhalides. VI. Bromination of Aromatic Amines by Use of Benzyltrimethylammonium Tribromide
  作者：Shoji Kajigaeshi、Takaaki Kakinami、Kazuhisa Inoue、Manabu Kondo、Hiroko Nakamura、Masahiro Fujikawa、Tsuyoshi Okamoto

  DOI：10.1246/bcsj.61.597

  日期：1988.2

  The reaction of aromatic amines with benzyltrimethylammonium tribromide in dichloromethane–methanol containing calcium carbonate powder for 0.5 h at room temperature gave bromo-substituted aromatic amines in good yields.

  芳香胺与三溴化苄基三甲基铵在含有碳酸钙粉末的二氯甲烷-甲醇中在室温下反应 0.5 小时，以良好的收率得到溴取代的芳香胺。
• Making endo-cyclizations favorable again: a conceptually new synthetic approach to benzotriazoles <i>via</i> azide group directed lithiation/cyclization of 2-azidoaryl bromides
  作者：Alexandra A. Ageshina、Gleb A. Chesnokov、Maxim A. Topchiy、Igor V. Alabugin、Mikhail S. Nechaev、Andrey F. Asachenko

  DOI：10.1039/c9ob00615j

  日期：——

  in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho–X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities

  尽管苯并三唑是重要的且无处不在，但目前仅有一种概念上的合成方法：将两个邻氨基与亲电氮原子桥连。在此，我们公开了新的可行的选择-将内获得2 azidoaryl lithiums -cyclization原位从2 azidoaryl溴化物。使用二十四个带有各种烷基，烷氧基，全氟烷基和卤素取代基的实例来说明反应的范围。我们发现叠氮化物基团的导向作用允许在含有几个溴原子的芳基叠氮化物中进行选择性的金属-卤素交换。此外，（2-溴苯基）重氮甲烷经历类似的环化以生成吲唑。因此，芳基锂的环化包含邻-X = Y = Z基团是合成芳族杂环的一种新的通用方法。DFT计算表明，观察到的内选择性适用于经历“ 1,1-加成”（即叠氮化物，重氮化合物和异腈）的其他官能团的阴离子环化反应。与此相反，与遵循“1,2-加成”图案（氰酸酯，硫氰酸酯，异氰酸酯，异硫氰酸酯，和腈）的杂原子官能团的环化反应倾向于外-cyclizat
• FR1536991
  申请人：——

  公开号：——

  公开（公告）日：——
• Bamberger, Justus Liebigs Annalen der Chemie, 1921, vol. 424, p. 300
  作者：Bamberger

  DOI：——

  日期：——
• CH607888
  申请人：——

  公开号：——

  公开（公告）日：——