2,4,6-Trinitrobenzyl chloride | 7176-28-5

• 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-Trinitrobenzyl chloride
• 英文别名: 2,4,6-trinitro-benzyl chloride；2,4,6-Trinitro-benzylchlorid；2,4,6-Trinitrobenzylchlorid；2-(Chloromethyl)-1,3,5-trinitrobenzene
• CAS: 7176-28-5
• 化学式: C₇H₄ClN₃O₆
• 分子量: 261.578
• InChiKey: PUJXVDWGOSEZMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,4,6-Trinitrobenzyl chloride 在 1-dodecyl-3-methylimidazolium cuprous chloride 、 铜 、 锌 作用下， 反应 2.5h， 以91%的产率得到1,2-bis(2,4,6-trinitrophenyl)ethane
  参考文献：
  名称：

  Facile and Efficient Reductive Homocoupling of Benzyl and Aryl Halides Catalyzed by Ionic Liquid [C12mim][CuCl2] in the Presence of Metallic Zinc and Copper

  摘要：

  A facile and efficient synthesis of bibenzyl and biaryl derivatives by reductive homocoupling reaction is described. Treatment of benzyl and aryl halides with metallic zinc and copper powder in the presence of a catalytic amount of [C(12)mim][CuCl2] under ligand- and base-free conditions gives the corresponding bibenzyls and biaryls in good to high yields. The product can be isolated by a simple extraction with organic solvent, and the catalytic system can be recycled or reused without any significant loss of catalytic activity.

  DOI：

  10.1007/s10562-010-0535-5
• 作为产物：
  描述：

  2,4,6-三硝基甲苯 在 sodium hypochlorite 作用下， 生成 2,4,6-Trinitrobenzyl chloride
  参考文献：
  名称：

  Reactions of α-Substituted Polynitrotoluenes. II. The Generation and Reactions of 2,4,6-Trinitrobenzyl Anion

  摘要：

  DOI：

  10.1021/jo01341a050

文献信息

• Kinetic study of proton/deuteron transfer reactions of 2,4,6-trinitrotoluene and its derivatives with tertiary amines
  作者：Yoshimi Sueishi、Takanori Fujimoto、Tohru Yoshida、Takeharu Kurita、Shunzo Yamamoto、Norio Nishimura

  DOI：10.1002/poc.610080602

  日期：1995.6

  parameteres were calculated semi-empirically on the basis of Bell's theory. The observed rate constants at low temperatures agreed well with the predicted values. In the present systems, some side and consecutive reactions involving the formation of 2,2′,4,4′6,6′-hexanitrostilbene took place, and in some cases interrupted the rate measurements in the proton/deuteron transfer steps.

  2,4,6-三硝基甲苯（TNT），2,2'4,4'6,6'-六硝基联苄（HNBB）和2,4,6-三硝基苄基氯（TNB）的质子/氘代转移反应速率分光光度法跟踪叔胺。根据同位素，溶剂和空间效应解释了在各种条件下获得的速率常数。TNT和TNB在低温下的Arrhenius曲线向上弯曲，清楚地表明了隧道效应。隧道参数是根据Bell理论半经验地计算的。在低温下观察到的速率常数与预测值非常吻合。在本系统中，发生了涉及形成2,2'，4,4'6,6'-六硝基二苯乙烯的副反应和连续反应，并且在某些情况下中断了质子/氘核转移步骤中的速率测量。
• Chemoenzymatic Synthesis of Trinitrobenzyl Halides as an Alternative Approach to Hexanitrostilbene
  作者：Inmar Z. Munir、Shanghui Hu、Jonathan S. Dordick

  DOI：10.1002/1615-4169(200212)344:10<1097::aid-adsc1097>3.0.co;2-s

  日期：2002.12

  The selective oxidation and halogenation of nitroaromatics is a difficult task both chemically and enzymatically. We have discovered that vanadium chloroand bromoperoxidases from Curvularia inaequalis and Corralina officinalis, respectively, are capable of catalyzing the hydroxylation, halogenation, and demethylation of 2,4,6-trinitrotoluene (TNT) under alkaline conditions. At pH 8, the conversions

  硝基芳烃的选择性氧化和卤化在化学和酶学上都是一项艰巨的任务。我们发现，来自不等弯弯菌和 Corralina officinalis 的氯钒和溴过氧化物酶分别能够在碱性条件下催化 2,4,6-三硝基甲苯 (TNT) 的羟基化、卤化和去甲基化。在 pH 值为 8 时，羟基化和去甲基化的转化率分别达到 38% 和 45%，而直接卤化作用最小。钒氯过氧化物酶生成三硝基苯甲醇，初始速率为 0.27 M/h-单位酶，而钒溴过氧化物酶的初始速率为 0.11 M/h-单位酶。酶促反应产物易于分离纯化，未反应底物回收。在 PCl5 存在下，钒氯过氧化物酶产生的三硝基苄醇很容易转化为三硝基苄基氯 (TNBCl)。这种化学酶合成可能有助于环境友好地合成六硝基芪，六硝基芪是耐热炸药材料的关键成分。
• The stabilities of Meisenheimer complexes. Part 21. Sulphite additions to 2,4,6-trinitrotoluene and 2,4,6-trinitrobenzyl chloride
  作者：David N. Brooke、Michael R. Crampton

  DOI：10.1039/p29800001850

  日期：——

  In aqueous sodium sulphite solutions, 2,4,6-trinitrotoluene and 2,4,6-trinitrobenzyl chloride give 1 : 1 and 1 : 2 adducts by addition at unsubstituted ring positions. Rate and equilibrium data for these reactions have been obtained by the stopped-flow method and are compared with similar data for other nitro-compounds.

  在亚硫酸钠水溶液中，通过在未取代的环位置加成，得到2,4,6-三硝基甲苯和2,4,6-三硝基苄基氯，形成1：1和1：1的加合物。这些反应的速率和平衡数据已通过停流方法获得，并与其他硝基化合物的相似数据进行了比较。
• Method for the production of hexanitrostilbene
  申请人：The United States of America as represented by the Secretary of the Navy

  公开号：US04199532A1

  公开（公告）日：1980-04-22

  A method of preparing 2,2',4,4',6,6'-hexanitrostilbene from 2,4,6-trinitrnzyl chloride and hydroxyl ions using an organic solvent-water two phase system and a phase transfer catalyst.

  使用有机溶剂-水两相系统和相转移催化剂，从2,4,6-三硝基苯甲酰氯和羟基离子制备2,2',4,4',6,6'-六硝基二苯乙烯的方法。
• HNS From 2,4,6-trinitrobenzyl chloride and nitrogenous bases
  申请人：The United States of America as represented by the Secretary of the Army

  公开号：US04307258A1

  公开（公告）日：1981-12-22

  2,4,6,-trinitrobenzyl chloride is converted to HNS (2,2',4,4',-6,6'-hexanostilbene) by reaction with hydroxide ion supplied by aqueous amines and ammonia. The present method increases the yield of HNS substantially over that obtainable by conventional reaction with sodium hydroxide.

  2,4,6-三硝基苯甲酰氯通过与水相胺和氨提供的羟基离子反应，转化为HNS(2,2',4,4',-6,6'-六烷基二苯乙烯)。该方法相较于传统的与氢氧化钠反应方式，可显著提高HNS的产率。