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

• 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：——
• Process for preparing benzotrifluoride and its derivatives
  申请人：Daikin Kogyo Co., Ltd.

  公开号：EP0004636B1

  公开（公告）日：1982-07-07