3-Chloronitrobenzene radical anion | 34467-54-4

• 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: 3-Chloronitrobenzene radical anion
• 英文别名: 3-chloronitrobenzene anion；m-chloronitrobenzene anion；m-Nitrochlorobenzol-Anion
• CAS: 34467-54-4；121-73-3
• 化学式: C₆H₄ClNO₂
• 分子量: 157.556
• InChiKey: KRESEJXYPDHMQR-UHFFFAOYSA-N

物化性质

• 熔点：
  43-47 °C(lit.)
• 沸点：
  236 °C(lit.)
• 密度：
  1.534 g/mL at 25 °C(lit.)
• 闪点：
  218 °F
• 溶解度：
  加热时易溶于酒精。
• LogP：
  2.49

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

制备方法与用途

化学性质

淡黄色晶体。相对密度1.534，熔点44℃， 沸点235.5℃。不溶于水，可溶于热乙醇、乙醚等大多数有机溶剂。还原时生成间氨基氯苯。由硝基苯在碘存在下氯化而制得。

化学性质 

浅黄色斜方棱晶。 微溶于水，溶于乙醇、乙醚、苯等大多数有机溶剂。

用途 

用于制造间氯苯胺、偶氮染料、颜料、药物、杀虫剂等

用途 

有机合成原料，染料中间体，用于制间氯苯胺，亦用于医药工业。

用途 

用于有机合成，也用作染料中间体

用途 

生化研究

用途 

间氯硝基苯是重要的染料、医药中间体，主要用于合成间氯苯胺、间二氯苯等。

用途 

本品是重要的染料、医药中间体，主要用于合成间氯苯胺、间二氯苯等。

生产方法 

1.由硝基苯在铁屑存在下氯化而得。在氯化塔中加入干燥的硝基苯和铁屑，通氯气，反应温度控制在40-45℃。当反应物料相对密度为1.35（25℃）、凝固点为23℃时，即为终点，停止通氯。用压缩空气吹除氯及氯化氢3h，将氯化物料用水洗至中性，进行减压分馏，切取凝固点22℃以上的馏分放入结晶器，冷却，降温至13℃，保持2h，然后升温，至凝固点为43℃时，将结晶器内物料熔解，得产品。2.在生产对硝基氯苯时有少量副产，可富集间位后，再精馏、结晶而得成品。

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 LD50：380 毫克/公斤

可燃性危险特性

遇明火可燃； 燃烧产生有毒氯化物和氮氧化物烟雾

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、砂土、雾状水

职业标准

TWA 1 毫克/立方米；STEL 2 毫克/立方米

反应信息

• 作为反应物：
  描述：

  3-Chloronitrobenzene radical anion 在 水 、 dioxide titanium 、 异丙醇 作用下， 生成 3-硝基氯苯
  参考文献：
  名称：

  Photocatalytic Reduction of Nitroorganics over Illuminated Titanium Dioxide:  Electron Transfer between Excited-State TiO₂ and Nitroaromatics

  摘要：

  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.

  DOI：

  10.1021/jp973224l
• 作为产物：
  描述：

  3-硝基氯苯 在 e(-) 作用下， 生成 3-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

• Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones
  作者：Elaine K. Fukuda、Robert T. McIver

  DOI：10.1021/ja00294a014

  日期：1985.4

  On determine les affinites electroniques de 53 molecules en mesurant les constantes d'equilibre des reactions de transfert d'electron en phase gazeuse du type A −• +B=B −• +A. On utilise un spectrometre a resonance cyclotronique ionique pour generer, stocker et detecter les radicaux anioniques moleculaires a des pressions inferieures a 1×10 −5 torr

  在确定 les affinites electroniques de 53 分子 en mesurant les constantes d'equilibre des reactors de transfert d'electron en phasegazeuse du type A −• +B=B −• +A。使用联合国光谱仪共振回旋离子离子倾倒生成器、斯托克和检测器 les radicaux anioniques molculaires a despressions inferieures a 1×10 -5 torr
• 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.
• Kinetic models for gas-phase electron-transfer reactions between nitrobenzenes
  作者：Chau Chung Han、James L. Wilbur、John I. Brauman

  DOI：10.1021/ja00029a014

  日期：1992.1

  Rate constants for gas-phase electron-transfer reactions between substituted nitrobenzenes have been measured using ion cyclotron resonance spectroscopy. On the basis of the assumption that these reactions occur through the formation of an intermediate complex, a statistical model is used to interpret the reaction kinetics. The intersecting parabolas quantum mechanical model provides an alternative description of the energy surface. Energy barriers are found to be consistent for the two methods. The results for exothermic reactions are consistent with a Marcus theory analysis, but suggest that a zero-order potential energy surface may not be completely adequate for quantitative prediction of reaction rates.