2,3,4-trichloro-1-(trichloromethyl)benzene | 20020-72-8

• 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: 2,3,4-trichloro-1-(trichloromethyl)benzene
• 英文别名: 1,2,3-trichloro-4-trichloromethyl-benzene；1,2,3-Trichlor-4-trichlormethyl-benzol；2,3,4-Trichlorbenzotrichlorid；1,2,3-Trichloro-4-(trichloromethyl)benzene
• CAS: 20020-72-8
• 化学式: C₇H₂Cl₆
• 分子量: 298.811
• InChiKey: GXEUUGWYEFEZQH-UHFFFAOYSA-N

物化性质

• 沸点：
  120-120.5 °C(Press: 0.13 Torr)
• 密度：
  1.70 g/cm3(Temp: 25 °C)

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：

  2,3,4-trichloro-1-(trichloromethyl)benzene 在 硫酸 、 甲基安非他命 作用下， 生成 2,3,4-三氯苯甲酸
  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：

  三氯苯 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 反应 10.0h， 生成 2,3,4-trichloro-1-(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

文献信息

• (Cycloalkyl)alkoxyimino-substituted cyclopropanecarboxylate esters, process for their manufacture, pesticidal compositions containing them, and their use as pesticides
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0021520A1

  公开（公告）日：1981-01-07

  ovel pesticidally-active oxyimino-substituted -cylopropane- carboxylate esters have the following general formuta:- Artwork su wherein R1 represents a hydrogen atom, an alkyl group optionally-substituted by one or more halogen atoms, a (cycloalkyl)alkyl group optionally ring-substituted by one or more halogen atoms, a cycloalkyl group, an alkenyl group optionally-substituted by one or more halogen atoms or an alkynyl group or an aryl or aralkyl group each optionally ring-substituted by one or more halogen atoms; and R is in which R2 and R3 each independently is a hydrogen atom, a halogen atom an alkyl group or a nitro group, each Hal is independently a halogen atom R' is a hydrogen atom or a halogen atom and n is an integer of 1 to 5.

  图样 su 其中 R1 代表氢原子、任选被一个或多个卤素原子取代的烷基、任选被一个或多个卤素原子环取代的(环烷基)烷基、环烷基、任选被一个或多个卤素原子取代的烯基、或任选被一个或多个卤素原子环取代的炔基、或任选被一个或多个卤素原子环取代的芳基或芳烷基；并且 R 是 其中 R2 和 R3 各自独立地为氢原子、卤素原子、烷基或硝基，Hal 各自独立地为卤素原子 R' 为氢原子或卤素原子，n 为 1 至 5 的整数。
• Process for the production of 4-chloro-trichloro-methyl benzene
  申请人：DOWELANCO

  公开号：EP0534412A2

  公开（公告）日：1993-03-31

  4-Chlorobenzotrichloride was prepared by the chlorination of p-xylene in the vapor phase at a temperature above about 200°C in the presence of an activated carbon catalyst and water. An approximately 75 percent calculated yield was obtained at 250°C using a wide-pore activated carbon catalyst.

  在活性炭催化剂和水的存在下，对二甲苯在气相中于约 200°C 以上的温度下进行氯化反应，制备出 4-氯三氯甲苯。使用宽孔活性炭催化剂，在 250°C 时可获得约 75% 的计算收率。
• Verbessertes Verfahren zur Herstellung von gegebenenfalls substituierten Benzaldehyden
  申请人：BAYER AG

  公开号：EP0555698A1

  公开（公告）日：1993-08-18

  Ein besonders vorteilhaftes Verfahren zur Herstellung von gegebenenfalls substituierten Benzaldehyden durch Verseifung der entsprechenden Benzalchloride mit Schwefelsäure ist dadurch gekennzeichnet, daß man Wasser in Gegenwart von Schwefelsäure bei 20 bis 160°C vorlegt, das Benzalchlorid und gegebenenfalls einen Teil des Wassers bei dieser Temperatur zumischt, nach Beendigung der Reaktion die Säurephase von der organischen Phase abtrennt, die Säurephase ganz oder teilweise in den nächsten Ansatz zurückführt und aus der organischen Phase den erhaltenen Benzaldehyd gewinnt.

  通过相应的苯甲醛氯化物与硫酸的皂化反应制备任选取代的苯甲醛的一种特别有利的工艺，其特征在于：在 20 至 160°C 的硫酸存在下引入水，在此温度下加入苯甲醛氯化物和任选加入的部分水，反应完成后将酸相与有机相分离，将全部或部分酸相循环到下一批中，并从有机相中回收所获得的苯甲醛。
• Process for the production of 4-amino-3,5-dichlorobenzotrifluoride with high purity commercial products being obtained in parallel
  申请人：FINCHIMICA S.p.A.

  公开号：EP1528052A1

  公开（公告）日：2005-05-04

  Process for the production of 4-amino-3,5-dichlorobenzotrifluoride comprising the stages: A) chlorination of 4-chlorobenzotrichloride, in the presence of a Lewis acid, in order to obtain a mixture of 3,4-dichlorobenzotrichloride and 3,4,5-trichlorobenzotrichloride and other chlorine derivatives by performing the reaction in such a manner as to obtain in the mixture of reaction products a quantity of 3,4,5-trichlorobenzotrichloride of greater than 10% by weight and preferably of between 20% and 30% by weight and a concentration of 3,4-trichlorobenzotrichloride of less than 90% by weight and preferably of between approx. 55% and 75% by weight, relative to the total weight of the chlorinated derivatives; B) fluorination with hydrofluoric acid of the mixture of chlorination products as obtained in stage A) in order to obtain the corresponding benzotrifluorides; and C) separation by distillation of the mixture of products of stage B) in order to obtain 3,4,5-trichlorobenzotrifluoride or an isomeric mixture of 3,4,5- and 2,4,5-trichlorobenzotrifluoride; and D) amination of 3,4,5-trichlorobenzotrifluoride or of said isomeric mixture.

  生产4-氨基-3,5-二氯三氟甲苯的工艺，包括以下阶段： A) 在路易斯酸存在下，对 4-氯三氯甲苯进行氯化，以获得 3,4-二氯三氯甲苯和 3,4,5-三氯三氯甲苯及其他氯衍生物的混合物，反应方式为在反应产物混合物中获得一定量的 3、按重量计，3,4,5-三氯三苯的浓度大于 10%，最好在 20%至 30%之间；按重量计，3,4-三氯三苯的浓度小于 90%，最好在约 55%至 75%之间。相对于氯化衍生物总重量的 55%至 75%； B) 用氢氟酸对阶段 A 中得到的氯化产物混合物进行氟化，以得到相应的三氟甲苯；以及 C) 通过蒸馏分离 B 阶段的产品混合物，以获得 3,4,5-三氯三氟甲苯或 3,4,5-三氯三氟甲苯和 2,4,5-三氯三氟甲苯的异构体混合物；以及 D) 将 3,4,5-三氯三氟甲苯或上述异构体混合物胺化。
• Wertyporoch, Justus Liebigs Annalen der Chemie, 1932, vol. 493, p. 153,156, 164
  作者：Wertyporoch

  DOI：——

  日期：——