methyl 2,3,4-trichlorobenzoate | 89978-33-6

• 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: methyl 2,3,4-trichlorobenzoate
• 英文别名: 2.3.4-Trichlor-benzoesaeure-methylester；2,3,4-Trichlor-benzoesaeuremethylester
• CAS: 89978-33-6
• 化学式: C₈H₅Cl₃O₂
• 分子量: 239.485
• InChiKey: HROGZMXHUGOFGI-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  299.6±35.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-trichlorobenzoate 在 甲醇 、 sodium hydroxide 作用下， 以 水 为溶剂， 以90%的产率得到3,4-二氯苯甲酸甲酯
  参考文献：
  名称：

  Gassmann, Joerg; Voss, Juergen, Zeitschrift fur Naturforschung, B: Chemical Sciences, 2008, vol. 63, # 11, p. 1291 - 1299

  摘要：

  DOI：
• 作为产物：
  描述：

  三氯苯 在 三氯化铝 、 硫酸 、 甲基安非他命 作用下， 以 二硫化碳 为溶剂， 反应 34.0h， 生成 methyl 2,3,4-trichlorobenzoate
  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

• Free-radical reactions of halogenated bridged polycyclic compounds. Part V. The addition of thiols and bromotrichloromethane to 1,2,3,4-tetrachloro-7,7-dimethoxynorborna-2,5-diene and the preparation of 1,2,3,4-tetrachloro-7,7-dimethoxyquadricyclene
  作者：D. I. Davies、P. J. Rowley

  DOI：10.1039/j39670002245

  日期：——

  7-dimethoxynorborna-2,5-diene (Ia) affords 1,4,5,6-tetrachloro-7,7-dimethoxynorborn-5-en-2-endo-yl alkyl sulphides (IV) and 1,2,3,5-endo-tetrachloro-6,6-di-methoxynorborn-2-en-7-syn-yl alkyl sulphides (V). Bromotrichloromethane affords 5-exo-bromo-1,2,3,5-endo-tetrachloro-6,6-dimethoxy-7-syn-trichloromethylnorborn-2-ene (XI) as sole product. The results are compared with those of similar reactions of

  将硫醇自由基加成到1,2,3,4-四氯-7,7-二甲氧基降冰片-2,5-二烯（Ia）中得到1,4,5,6-四氯-7,7-二甲氧基降冰片-5 -en-2-内-烷基硫化物（IV）和1,2,3,5-内-四氯-6,6-二甲氧基降冰片-2-en-7-顺基烷基硫化物（V）。溴三氯甲烷可提供5- exo-溴-1,2,3,5-内-四氯-6,6-二甲氧基-7-辛基-三氯甲基降冰片-2-烯（XI）为唯一产物。将结果与六氯降冰片二烯（Ib）的类似反应进行了比较，得出的结论是，C-7取代基的大空间尺寸控制自由基的进攻方向。C-7处的甲氧基取代基似乎能以少于氯取代基的硫醇来阻止链转移：相反的情况适用于溴代三氯甲烷的链转移。报道了1,2,3,4-四氯-7,7-二甲氧基四氢环戊烯（XII）的制备。
• Direct C–H Carboxylation Forming Polyfunctionalized Aromatic Carboxylic Acids by Combined Brønsted Bases
  作者：Masanori Shigeno、Kazuya Hanasaka、Itsuki Tohara、Koki Izumi、Hiroyuki Yamakoshi、Eunsang Kwon、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1021/acs.orglett.1c03866

  日期：2022.1.28

  CO2 fixation into electron-deficient aromatic C–H bonds proceeds with the combined Brønsted bases LiO-t-Bu and LiO-t-Am/CsF/18-crown-6 (t-Am = CEtMe2) under a CO2 atmosphere to afford a variety of polyfunctionalized aromatic carboxylic acids.

  在 CO 2气氛下，通过组合的布朗斯台德碱 LiO- t -Bu 和 LiO- t -Am/CsF/18-crown-6 ( t -Am = CEtMe 2 ) 将CO 2固定成缺电子芳族 C-H 键以提供多种多官能化芳族羧酸。
• 86. The reaction of hexachlorobicyclo[2,2,1]heptadiene with potassium ethoxide
  作者：K. Mackenzie

  DOI：10.1039/jr9620000457

  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：——
• 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
  作者：J. Castaner、J. Riera、J. Carilla、A. Robert、E. Molins、C. Miravitlles

  DOI：10.1021/jo00001a022

  日期：1991.1

  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.