(2,4,5-三甲基苯基)硝基甲烷 | 60368-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2,4,5-三甲基苯基)硝基甲烷
• 英文名称: (2,4,5-trimethylphenyl)nitromethane
• 英文别名: 2,4,5-trimethylphenylnitromethane；1,2,4-trimethyl-5-nitromethyl-benzene；1,2,4-Trimethyl-5-nitromethyl-benzol；2,4,5-Trimethylphenylnitromethan；2,4,5-Trimethylbenzylnitrat；Nitrodurene；1,2,4-trimethyl-5-(nitromethyl)benzene
• CAS: 60368-03-8
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: PHOUHVCAPAOEBH-UHFFFAOYSA-N

物化性质

• 熔点：
  52.5 °C
• 沸点：
  14.3-14.4 °C(Press: 10 Torr)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,4,5-三甲基苯基)硝基甲烷 在 alkali 作用下， 生成 1,2,4-trimethyl-5-aci-nitromethyl-benzene
  参考文献：
  名称：

  Willstaetter; Kubli, Chemische Berichte, 1909, vol. 42, p. 4163

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,4-三甲基苯 在 盐酸 、 silver(I) nitrite 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 9.0h， 生成 (2,4,5-三甲基苯基)硝基甲烷
  参考文献：
  名称：

  Direct observation of the kinetic acidities of transient aromatic cation radicals. The mechanism of electrophilic sidechain nitration of the methylbenzenes

  摘要：

  DOI：

  10.1021/ja00188a048

文献信息

• PROCESS FOR THE PREPARATION OF NITRO COMPOUNDS AND METHOD FOR THE REMOVAL OF NITROGEN DIOXIDE
  申请人：Daicel Chemical Industries, Ltd.

  公开号：EP1099684A1

  公开（公告）日：2001-05-16

  In the invented process for producing a nitro compound, an organic substrate and nitrogen dioxide are reacted in the presence of oxygen or are reacted in a molar ratio of nitrogen dioxide to the organic substrate of less than 1 to yield a corresponding nitro compound. The reaction may be performed in the presence of N-hydroxyphthalimide or other imide compounds. Such organic substrates include (a) aliphatic hydrocarbons, (b) alicyclic hydrocarbons, (c) non-aromatic heterocyclic compounds each having a carbon atom on a ring, which carbon atom is bonded to a hydrogen atom, (d) compounds each having a carbon-hydrogen bond at the adjacent position to an aromatic ring, and (e) compounds each having a carbon-hydrogen bond at the adjacent position to a carbonyl group. This process can efficiently nitrate an organic substrate even under relatively mild conditions.

  在制备硝基化合物的发明过程中，有机底物和二氧化氮在氧气存在下反应，或者在二氧化氮与有机底物的摩尔比小于1的情况下反应，以产生相应的硝基化合物。该反应可以在N-羟基邻苯二甲酰亚胺或其他亚酰胺化合物存在下进行。这样的有机底物包括(a) 脂肪烃，(b) 脂环烃，(c) 非芳香杂环化合物，每个环上的碳原子与氢原子相结合，(d) 每个化合物在芳香环旁边位置具有碳氢键，以及(e) 每个化合物在酮基旁边位置具有碳氢键。这个过程可以在相对温和的条件下有效地对有机底物进行硝化。
• Thermal and Photochemical Nitration of Aromatic Hydrocarbons with Nitrogen Dioxide
  作者：E. Bosch、J. K. Kochi

  DOI：10.1021/jo00091a018

  日期：1994.6

  Aromatic hydrocarbons (ArH) are readily nitrated by nitrogen dioxide (NO2) in dichloromethane at room temperature and below (in the dark). The red colors, transiently observed, arise from the metastable precursor complex [ArH, NO+]NO3-, which is formed in the prior disproportionation of nitrogen dioxide induced by the aromatic donor (eq 7). The deliberate irradiation of the diagnostic (red) charge-transfer absorption band (h nu(CT)) of [ArH, NO+] NO3- at low temperatures results directly in aromatic nitration, even at -78 degrees C, where the thermal nitration is too slow to compete. The mechanism of the photochemical (charge-transfer) nitration is established by time-resolved laser spectroscopy to proceed via the aromatic cation radical (ArH.+) formed spontaneously upon the charge-transfer excitation of [ArH, NO+]NO3- in Scheme 1. The related thermal activation of [ArH, NO+]NO3- derives from the adiabatic electron transfer that produces the same radical pair [ArH.+ NO.] as the reactive intermediate in Scheme 3. The close relationship between the thermal/photochemical nitrations with nitrogen dioxide and those conventionally carried out with nitric acid (in the presence of nitrous acid) is delineated by Scheme 4.
• Blackstock,D.J. et al., Australian Journal of Chemistry, 1973, vol. 26, p. 775 - 783
  作者：Blackstock,D.J. et al.

  DOI：——

  日期：——
• Oxidative aromatic nitration with charge-transfer complexes of arenes and nitrosonium salts
  作者：E. K. Kim、J. K. Kochi

  DOI：10.1021/jo00268a036

  日期：1989.3
• Fischer,A.; Leonard,D.R.A., Canadian Journal of Chemistry, 1976, vol. 54, p. 1795 - 1806
  作者：Fischer,A.、Leonard,D.R.A.

  DOI：——

  日期：——