N-chloro-2,2,2-trifluoroethylamine | 1252686-20-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: N-chloro-2,2,2-trifluoroethylamine
• 英文别名: N-chloro-2,2,2-trifluoroethanamine
• CAS: 1252686-20-6
• 化学式: C₂H₃ClF₃N
• 分子量: 133.501
• InChiKey: VZNTZVQSRWFHCF-UHFFFAOYSA-N

物化性质

• 沸点：
  33.4±35.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-chloro-2,2,2-trifluoroethylamine 在 sodium perchlorate 、 氢碘酸 作用下， 以 水 为溶剂， 生成 2,2,2-三氟乙基胺
  参考文献：
  名称：

  酸催化的氯从N-氯胺向碘离子的转移：机理预测变化的实验证据†

  摘要：

  酸催化下列反应的速率常数 N-氯二甲基胺（1），N-氯-2,2,2-三氟乙胺（2）和N，N-二氯牛磺酸（3）配合碘化物在25°C和I = 0.5（NaClO 4）的H 2 O中测定离子。无法检测到一般酸对下列物质的明显催化作用氯与观察到的逆溶剂一起从1转移到亲核试剂氘同位素对水合氢离子催化反应的影响（k H / k D = 0.37），表明此过程是通过在快速平衡步骤中质子化1进行的，随后进行速率确定氯 传送到 碘化物离子。对2和3反应的一般酸催化作用的出现表明，离去基团能力的提高导致协调机制的改变，这被认为是由于缺乏质子化的显着寿命而引起的。氯胺 中间存在 碘化物 离子。

  DOI：

  10.1039/c004976j
• 作为产物：
  描述：

  2,2,2-三氟乙胺盐酸盐 在 次氯酸叔丁酯 、 sodium perchlorate 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 生成 N-chloro-2,2,2-trifluoroethylamine
  参考文献：
  名称：

  氯化与次氯酸叔丁酯（TBuOCl）的反应

  摘要：

  研究了含氮有机化合物（2,2,2-三氟乙胺，苄胺，甘氨酸和二甲胺）在25°C，离子强度0.5 M和隔离条件下于次氯酸叔丁酯（t BuOCl）的氯化反应。本文总结了在酸性介质（pH = 5-7）中相应的N-氯胺形成过程中获得的动力学结果。动力学研究表明相对于t而言是一阶的BuOCl浓度。相对于含氮化合物的浓度，涉及苄胺，甘氨酸和二甲胺的氯化反应均为一阶，相对于质子浓度而言约为一阶。与2,2,2-三氟乙胺的反应更加复杂，并且相对于胺的反应顺序随pH的变化而变化。版权所有©2014 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.3377

文献信息

• Use of N-chloro-N-methyl-p-toluenesulfonamide in N-chlorination reactions
  作者：Cristina Pastoriza、Juan Manuel Antelo、Juan Crugeiras

  DOI：10.1002/poc.3127

  日期：2013.7

  Second-order rate constants (k2) were determined for the addition of ten nitrogenous organic compounds (benzylamine, 2,2,2-trifluoethylamine chlorhidrate, methylamine chlorhidrate, glycine ethyl ester chlorhidrate, glycine, glycylglycine chlorhidrate, morpholine, pyperidine, pyperazine and dimethylamine) to the N-chloro-N-methyl-p-toluenesulfonamide (NCNMPT) in the formation reaction of N-chloramines in aqueous solution at 25 degrees C and ionic strength 0.5M. The series of nucleophiles considered is structurally very varied and covers five pKa units. The kinetic behaviour is similar for all compounds, being the elementary step the transfer of chlorine from the NCNMPT molecule to the nitrogen of the free amino group. These reactions were found first order in both reagents. The values of the rate constants indicate that the more basic amines produce N-chloramines more readily. Rate constants for the nucleophilic attack are shown to correlate with literature data for some of these nitrogenous organic compounds in their reaction with N-methyl-N-nitroso-p-toluenesulfonamide. Both reactions involve that the rate determining step is the attack of nitrogenous compounds upon electrophilic centre (Cl or else NO group). NCNMPT is a particularly interesting substrate, for which has not hitherto been published kinetic information, that allows us to assess the efficiency and the competitiveness of this reaction and compare it with other agents with a Cl+ atom. Copyright (c) 2013 John Wiley & Sons, Ltd.
• Kinetic study of the formation of<i>N</i>-chloro compounds using<i>N</i>-chlorosuccinimide
  作者：Cristina Pastoriza、Juan Manuel Antelo、Juan Crugeiras、Angeles Peña-Gallego

  DOI：10.1002/poc.3278

  日期：2014.5

  Second‐order rate constants were determined for the chlorination reaction of 2,2,2‐trifluoethylamine and benzylamine with N‐chlorosuccinimide at 25 °C and an ionic strength of 0.5 M. These reactions were found to be of first order in both reagents. According to the experimental results, a mechanism reaction was proposed in which a chlorine atom is transferred between both nitrogenous compounds. Kinetics studies demonstrate that the hydrolysis process of the chlorinating agent does not interfere in the chlorination process, under the experimental conditions used in the present work. Free‐energy relationships were established using the results obtained in the present work and others available in the literature for chlorination reactions with N‐chlorosuccinimide, being the pKa range included between 5.7 and 11.22. Copyright © 2014 John Wiley & Sons, Ltd.
• Reactions of chlorination with<i>tert</i>-butyl hypochlorite (^TBuOCl)
  作者：Cristina Pastoriza、Juan Manuel Antelo、Juan Crugeiras

  DOI：10.1002/poc.3377

  日期：2014.12

  The chlorination reactions of nitrogenous organic compounds (2,2,2‐trifluoroethylamine, benzylamine, glycine, and dimethylamine) by tert‐butyl hypochlorite (tBuOCl) were studied at 25 °C, ionic strength 0.5 M and under isolation conditions. The kinetic results obtained in the formation processes of the corresponding N‐chloramines in acid medium (pH = 5–7) are summarized in this paper. Kinetic studies

  研究了含氮有机化合物（2,2,2-三氟乙胺，苄胺，甘氨酸和二甲胺）在25°C，离子强度0.5 M和隔离条件下于次氯酸叔丁酯（t BuOCl）的氯化反应。本文总结了在酸性介质（pH = 5-7）中相应的N-氯胺形成过程中获得的动力学结果。动力学研究表明相对于t而言是一阶的BuOCl浓度。相对于含氮化合物的浓度，涉及苄胺，甘氨酸和二甲胺的氯化反应均为一阶，相对于质子浓度而言约为一阶。与2,2,2-三氟乙胺的反应更加复杂，并且相对于胺的反应顺序随pH的变化而变化。版权所有©2014 John Wiley＆Sons，Ltd.
• Acid-catalysed chlorine transfer from N-chloramines to iodide ion: experimental evidence for a predicted change in mechanism
  作者：Paula Calvo、Juan Crugeiras、Ana Ríos

  DOI：10.1039/c004976j

  日期：——

  iodide ion were determined in H2O at 25 °C and I = 0.5 (NaClO4). The failure to detect significant catalysis by general acids of chlorine transfer from 1 to the nucleophile, together with the observed inverse solvent deuterium isotope effect on the hydronium ion-catalysed reaction (kH/kD = 0.37), indicates that this process occurs by protonation of 1 in a fast equilibrium step, followed by rate determining

  酸催化下列反应的速率常数 N-氯二甲基胺（1），N-氯-2,2,2-三氟乙胺（2）和N，N-二氯牛磺酸（3）配合碘化物在25°C和I = 0.5（NaClO 4）的H 2 O中测定离子。无法检测到一般酸对下列物质的明显催化作用氯与观察到的逆溶剂一起从1转移到亲核试剂氘同位素对水合氢离子催化反应的影响（k H / k D = 0.37），表明此过程是通过在快速平衡步骤中质子化1进行的，随后进行速率确定氯 传送到 碘化物离子。对2和3反应的一般酸催化作用的出现表明，离去基团能力的提高导致协调机制的改变，这被认为是由于缺乏质子化的显着寿命而引起的。氯胺 中间存在 碘化物 离子。