4-Chloronitrobenzene radical anion | 34473-09-1

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 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: 4-Chloronitrobenzene radical anion
• 英文别名: p-Nitrochlorobenzol-Anion
• CAS: 34473-09-1；100-00-5
• 化学式: C₆H₄ClNO₂
• 分子量: 157.556
• InChiKey: VWZIFRSRCLGXBS-UHFFFAOYSA-N

物化性质

• 熔点：
  80-83 °C(lit.)
• 沸点：
  242 °C(lit.)
• 密度：
  1.298 g/mL at 25 °C(lit.)
• 蒸气密度：
  5.4 (vs air)
• 闪点：
  >230 °F
• 溶解度：
  溶于丙酮和酒精 (Weast, 1986)
• 暴露限值：
  Potential occupational carcinogen. NIOSH REL: IDLH 100; OSHA PEL: TWA 1.

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  0.0
• 氢受体数：
  2.0

安全信息

• TSCA：
  Yes
• 危险等级：
  6.1
• 立即威胁生命和健康浓度：
  100 mg/m3

制备方法与用途

化学性质 

浅黄色结晶。 难溶于水（25℃时仅溶0.03%），微溶于冷乙醇，溶于热乙醇、乙醚、丙酮和苯等有机溶剂。

用途 

是制造偶氮染料及硫化染料、药物非那西丁及扑热息痛、农药除草醚等的重要中间体，也是橡胶防老剂4010的原料

用途 

制备染料（偶氮染料、硫化染料）、医药（非那西丁、扑热息痛）、农药（除草醚）的重要中间体。也可作橡胶防老剂4010等的原料。对硝基氯苯的衍生物对硝基酚钠，主要用作1605的中间体；用对硝基氯苯生产的除草剂草枯醚。

用途 

用于有机合成，也用作染料中间体

用途 

对硝基氯苯是重要的有机合成中间体，广泛应用于染料、农药、医药及橡胶工业中。

生产方法 

将硝酸、硫酸配成混酸后，与氯苯进行硝化反应，生成硝基氯苯（对位65%、邻位34%、间位1%），然后分离硝基氯苯和废酸。分离后硝基氯苯经水洗、中和、得中性硝基氯苯，再经干燥、结晶。分离出成品对硝基氯苯，共融油经精馏、脱焦、结晶得联产品邻硝基氯苯。

类别

有毒物品

毒性分级

高毒

急性毒性

口服-大鼠 LD50: 420 毫克/公斤; 口服-小鼠 LD50: 440 毫克/公斤

可燃性危险特性

明火可燃;高热分解有毒的氮氧化物和氯化物烟雾

储运特性

库房通风低温干燥; 与氧化剂、食品添加剂分开存放

灭火剂

二氧化碳、泡沫、水。

职业标准

TWA 1 毫克/立方米; STEL 3 毫克/立方米

反应信息

• 作为反应物：
  描述：

  4-Chloronitrobenzene radical anion 在 氧气 作用下， 35.0 ℃ 、399.97 Pa 条件下， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Reactions of selected molecular anions with oxygen

  摘要：

  使用脉冲电子束高压质谱仪研究了分子氧与通过共振电子捕获形成的 17 种化合物的分子阴离子的气相反应。发现六氟化硫、全氟甲基环己烷、顺式和反式全氟萘烷、间氯硝基苯、邻、间和对氟硝基苯以及邻、间和对二硝基苯的分子阴离子与氧不发生反应。人们发现邻氯硝基苯和对氯硝基苯、五氯苯和全氯苯、全氟苯和全氟甲苯很容易与氧气发生反应。这些反应的二阶速率常数与温度成反比。涉及邻氯硝基苯和对氯硝基苯以及五氯苯和全氯苯的反应通过支化机理进行，同时产生 [M + O − Cl]− 类型的离子和 Cl− 离子。全氟苯和全氟甲苯的分子阴离子与氧气反应时会形成更多种类的负离子。五氯苯（0.7 eV）和全氯苯（1.0 eV）的电子亲和势也是首次报道。

  DOI：

  10.1002/jms.1190300406
• 作为产物：
  描述：

  对硝基氯苯 在 e(-) 作用下， 生成 4-Chloronitrobenzene radical anion
  参考文献：
  名称：

  气相电子转移平衡引起的熵变和电子亲和力：A- + B = A + B-

  摘要：

  DOI：

  10.1021/j100403a037

文献信息

• Electron affinities from electron-transfer equilibria: A- + B = A + B-
  作者：Eric P. Grimsrud、Gary Caldwell、Swapan Chowdhury、Paul Kebarle

  DOI：10.1021/ja00302a005

  日期：1985.8

  L'etude est faite pour 34 composes, principalement des nitrobenzenes substitues, des quinones substituees et des molecules conjuguees contenant des atomes d'oxygene

  L'练习曲EST faite倾34层构成，principalement DES硝基苯subSTitues，脱醌subSTituees和des分子conjuguees contenant DES atomes D'OXYGENE
• Resonance Electron Capture Rate Constants for Substituted Nitrobenzenes
  作者：W. B. Knighton、R. S. Mock、D. S. McGrew、E. P. Grimsrud

  DOI：10.1021/j100065a036

  日期：1994.4

  We report here a new method for the determination of electron capture (EC) rate constants that utilizes a pulsed electron beam mass spectrometer. The method is first tested by measurements of the known dissociative electron capture rate constants for several halogenated methanes that have been extensively studied by other techniques. The resonance electron capture (REC) rate constants of nitrobenzene (NB) and 23 substituted nitrobenzenes (SNB's) are then determined for the first time at 125 degrees C in 10 Torr of methane buffer gas. The SNB's studied here include several sets of closely related structural isomers whose electron affinities (EA's) have been previously determined. It is shown that the REC rate constants of these compounds bear little systematic relationship with the EA's of these compounds. The REC rate constants of the SNB's are also compared with other previously reported characteristics associated with the negative ionization of these compounds, including their entropies of negative ionization, the lifetimes against autodetachment of their initially formed molecular anions, and the rates of autodetachment from electronically excited states of their molecular anions.
• Photocatalytic Reduction of Nitroorganics over Illuminated Titanium Dioxide:  Electron Transfer between Excited-State TiO₂ and Nitroaromatics
  作者：John L. Ferry、William H. Glaze

  DOI：10.1021/jp973224l

  日期：1998.3.1

  The present study investigates the steady-state photocatalytic reduction of methyl viologen and a suite of monosubstituted nitrobenzenes. Reduction was carried out in deoxygenated, illuminated aqueous slurries of titanium dioxide (Degussa P25) in the presence of a sacrificial electron donor, 2-propanol. Langmuir-Hinshelwood plots were obtained for the reduction of each compound and found to be linear, with an average correlation of 0.98 and with a standard deviation on the correlations of 0.02. The concentration independent rates for nitroaromatic reduction obtained from these plots were normalized against the rate of methyl viologen reduction, and the ratio was used to solve for the rate constant of nitroaromatic reduction, assuming a bimolecular model. The assumptions behind this procedure were tested by the use of the Marcus expression. Using the reorganization energy for the reaction as the fitting variable, it was possible to fit the measured rates to the predicted rates with a reorganization energy of 138 kJ/mol.
• One-electron reduction of nitrobenzenes by .alpha.-hydroxyalkyl radicals via addition/elimination. An example of an organic inner-sphere electron-transfer reaction
  作者：V. Jagannadham、S. Steenken

  DOI：10.1021/ja00334a015

  日期：1984.10