2,4,6-trichloro-1,3-bis(trifluoromethyl)benzene | 130199-73-4

• 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: 2,4,6-trichloro-1,3-bis(trifluoromethyl)benzene
• 英文别名: 1,3,5-trichloro-2,4-bis(trifluoromethyl)benzene
• CAS: 130199-73-4
• 化学式: C₈HCl₃F₆
• 分子量: 317.445
• InChiKey: MMYQNVDTWAJAMO-UHFFFAOYSA-N

物化性质

• 沸点：
  235.5±35.0 °C(Predicted)
• 密度：
  1.650±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2,4,6-trichloro-1,3-bis(trifluoromethyl)benzene 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 反应 6.0h， 以98%的产率得到2,4,6-trichloro-1,3-bis(trichloromethyl)benzene
  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 、 一氟三氯甲烷 在 三氯化铝 作用下， 以85.5%的产率得到2,4,6-trichloro-1,3-bis(trifluoromethyl)benzene
  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

文献信息

• Trifluoromethanesulfonic Anhydride as a Low-Cost and Versatile Trifluoromethylation Reagent
  作者：Yao Ouyang、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1002/anie.201803566

  日期：2018.6.4

  large number of reagents have been developed for the synthesis of trifluoromethylated compounds. However, an ongoing challenge in trifluoromethylation reaction is the use of less expensive and practical trifluoromethyl sources. We report herein the unprecedented direct trifluoromethylation of (hetero)arenes using trifluoromethanesulfonic anhydride as a radical trifluoromethylation reagent by merging photoredox

  已经开发了用于合成三氟甲基化化合物的大量试剂。然而，三氟甲基化反应中的持续挑战是使用较便宜且实用的三氟甲基来源。我们在此报道了通过合并光氧化还原催化作用和吡啶活化作用，使用三氟甲磺酸酐作为自由基三氟甲基化试剂，对（杂）芳烃进行了前所未有的直接三氟甲基化。此外，实现了将三氟甲磺酸酐的CF 3和OTf基团同时引入内部炔烃以进入四取代的三氟甲基化的烯烃。由于三氟甲磺酸酐是一种低成本且含量丰富的化学品，因此该方法为生产三氟甲基化化合物提供了一种经济高效的实用途径。
• 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：——