α,α,α,2,4,6-hexachlorotoluene | 14379-95-4

• 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: α,α,α,2,4,6-hexachlorotoluene
• 英文别名: 2,4,6-trichloro-1-(trichloromethyl)benzene；1,3,5-trichloro-2-(trichloromethyl)benzene
• CAS: 14379-95-4
• 化学式: C₇H₂Cl₆
• 分子量: 298.811
• InChiKey: OXOHTICHGYFWNF-UHFFFAOYSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  334.0±37.0 °C(Predicted)
• 密度：
  1.691±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  α,α,α,2,4,6-hexachlorotoluene 在 氯化亚砜 、 硫酸 、 甲基安非他命 、 氨 作用下， 反应 24.0h， 生成 2,4,6-三氯-苯甲酸酰胺
  参考文献：
  名称：

  A new trifluoromethylating agent: synthesis of polychlorinated (trifluoromethyl)benzenes and 1,3-bis(trifluoromethyl)benzenes and conversion into their trichloromethyl counterparts and molecular structure of highly strained polychloro-m-xylenes

  摘要：

  Mixtures of CCl3F and AlCl3 replace CF3 for H in polychlorobenzenes. Thus, by treatment of a solution of the suitable polychlorobenzene in CCl3F with AlCl3, the following compounds can be prepared: pentachloro- (2), 2,3,4,5-tetrachloro- (5), 2,3,4,6-tetrachloro- (8), 2,3,5,6-tetrachloro- (11), 2,3,4-trichloro- (14), 2,4,5-trichloro- (17), and 2,4,6-trichloro-1-(trifluoromethyl)benzene (20), as well as 4,5,6-trichloro- (31) and 2,4,6-trichloro-1,3-bis(trifluoromethyl)benzene (32). The reaction of the above-mentioned trifluoromethylated compounds with AlCl3 in CS2 yields their trichloromethyl counterparts: 3, 6, 9, 12, 15, 18, 21, 34, and 36. The chlorination of 32 or 36 by means of Silberrad's reagent (SO2Cl2, AlCl3, and S2Cl2) affords perchloro-m-xylene (38), a new highly strained chlorocarbon whose synthesis was attempted repeatedly in the past. 9, 15, 17, and 21, when treated with oleum and then with water, are converted into 2,3,4,6-tetrachloro- (22), 2,3,4-trichloro- (23), 2,4,5-trichloro- (24), and 2,4,6-trichlorobenzoic acid (25), respectively; under similar treatment, 34, 36, and 38 give 4,5,6-trichloro- (33), 2,4,5-trichloro- (35), and tetrachloroisophthalic acid (39), respectively. The formation of the (trifluoromethyl)benzenes is discussed, and in this connection it has been found that CCl3F solutions of 3 and 18 in the the presence of AlCl3 give back 2 and 17, respectively. Molecular structures of highly strained m-xylenes 36 and 38, as well as that of the much less strained 34, ascertained by X-ray analysis, are reported and commented. IR, UV, and NMR spectral data of the compounds synthesized are presented. The interesting UV spectrum of 21 is discussed.

  DOI：

  10.1021/jo00001a022
• 作为产物：
  描述：

  1,3,5-三氯苯 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 生成 α,α,α,2,4,6-hexachlorotoluene
  参考文献：
  名称：

  聚氯三氟甲苯和高应变聚氯三苯的新合成

  摘要：

  通过用CCl 3 F和AlCl 3处理相应的多氯苯，已经制备了几种多氯代三氟甲基苯。通过与相同的无机卤化物在CS 2中反应，得到的三氟甲基衍生物得到其三氯甲基类似物。

  DOI：

  10.1016/s0040-4039(01)80668-7
• 作为试剂：
  描述：

  3-甲基吡啶 在 α,α,α,2,4,6-hexachlorotoluene 作用下， 以 氯仿 为溶剂， 反应 720.0h， 以64%的产率得到2,4,6-三甲基苯甲醛
  参考文献：
  名称：

  还原剂的性质及三氯甲基芳烃与羟胺和肼在吡啶中的还原缩合机理

  摘要：

  DOI：

  10.1007/bf01169070

文献信息

• New synthesis of polychloro(trifluoromethyl)benzenes and highly strained polychloro(trichloromethyl)benzenes
  作者：Juan Riera、Juan Castañer、José Carilla、Ana Robert

  DOI：10.1016/s0040-4039(01)80668-7

  日期：1989.1

  Several polycloro(trifluoromethyl)benzenes have been prepared by treatment of the corresponding polychlorobenzenes with CCl3F and AlCl3. The resulting trifluoromethyl derivatives, by reaction with the same inorganic halide in CS2, give their trichloromethyl analogues.

  通过用CCl 3 F和AlCl 3处理相应的多氯苯，已经制备了几种多氯代三氟甲基苯。通过与相同的无机卤化物在CS 2中反应，得到的三氟甲基衍生物得到其三氯甲基类似物。
• 一种2,4,6-三氯苯甲酸的制备方法
  申请人：黑龙江立科新材料有限公司

  公开号：CN117586116A

  公开（公告）日：2024-02-23

  本发明提供一种2,4,6‑三氯苯甲酸的制备方法，该方法包括：1)使甲苯发生氯化反应，得到1,3,5‑三氯‑2‑(三氯甲基)苯；2)使所述1,3,5‑三氯‑2‑(三氯甲基)苯发生氧化反应，得到2,4,6‑三氯苯甲酸。该方法能够得到纯度高达99.6％和摩尔收率高达92.7％的2,4,6‑三氯苯甲酸，原料价格低廉，工艺简单，制备成本低，并且较为安全环保，能够适用于规模化生产。
• The first isolated carbon tetraradical with a pair of triplets
  作者：J. Carilla、L. Julia、J. Riera、E. Brillas、J. A. Garrido、A. Labarta、R. Alcala

  DOI：10.1021/ja00022a013

  日期：1991.10

  The synthesis of trans-perchlorovinylenebis(alpha,alpha,alpha',alpha'-tetraphenyl-,3-xylylene) (1), an exceptionally stable organic carbon tetraradical, which is isolated as a deep red solid, stable in air up to 200-degrees-C, is reported. The electronic spectrum of 1 is presented and commented on. The cyclic voltammogram of 1, exhibiting two consecutive redox couples with standard potentials of -0.175 and-0.480 V vs SCE, is discussed in view of the exhaustive controlled-potential electrolysis of the tetraradical into the corresponding tetraanion. Magnetic susceptibility measurements from 4.2 to 300 K show that a pair of triplets is the ground state of the tetraradical, being 2J = 240 +/- 10 cm-1 (0.69 kcal/mol), the triplet-singlet energy gap. At low temperatures, a weak antiferromagnetic interaction was observed (negative and low value of Weiss constant THETA = 1.1 +/- 0.1 K). From an EPR analysis in frozen 2-methyltetrahydrofuran over the range 4-129 K, the presence of two diastereoisomeric forms of the molecule is tentatively suggested. Accordingly, from the two symmetric and outer pairs of peaks of DELTA-m(s) = +/- 1 transition in the spectrum, two different \D/hc\ values, 0.010 and 0.013 cm-1, are calculated that are in good agreement with those reported for perchloro-m-xylylene. Supporting the presence of the two forms of 1, the DELTA-m(s) = +/- 2 transition exhibits two overlapping lines. The intensity of this transition rises continuously from 129 to 4 K, also supporting that the ground state is a pair of triplets.
• TETRAHEDRON LETT., 30,(1989) N9, C. 3825
  作者：

  DOI：——

  日期：——
• CASTANER, J.;RIERA, J.;CARILLA, J.;ROBERT, A.;MOLINS, E.;MIRAVITLLES, C., J. ORG. CHEM., 56,(1991) N, C. 103-110
  作者：CASTANER, J.、RIERA, J.、CARILLA, J.、ROBERT, A.、MOLINS, E.、MIRAVITLLES, C.

  DOI：——

  日期：——