sodium 3-methyl-4-nitrophenolate | 2666-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: sodium 3-methyl-4-nitrophenolate
• 英文别名: Natrium-3-methyl-4-nitrophenolat；sodium 4-nitro-m-cresolate；sodium 3-methyl-4-nitrophenate；Sodium;3-methyl-4-nitrophenolate；sodium;3-methyl-4-nitrophenolate
• CAS: 2666-76-4
• 化学式: C₇H₆NO₃*Na
• 分子量: 175.119
• InChiKey: DEQWBYKBSRNLCS-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.02
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  sodium 3-methyl-4-nitrophenolate 生成 4-硝基间甲苯酚
  参考文献：
  名称：

  ZELJAZKOV, VLADIMIR;HAUSKRECHT, PETER

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基间甲苯酚 生成 sodium 3-methyl-4-nitrophenolate
  参考文献：
  名称：

  摘要：

  DOI：

文献信息

• Method for the preparation of nitrodiphenyl ethers
  申请人：OCCIDENTAL CHEMICAL CORPORATION

  公开号：EP0173349A1

  公开（公告）日：1986-03-05

  Diphenyl ethers of the formula wherein m is an integer of 1 to 3, n is 1 or 2, R is hydrogen, carboxy, carboxylate salt or ester, formyl oxime, cyano, alkyl, alkoxy, chloro, bromo, or N, N-dialkyl amino, are prepared by reacting a chloro-fluoro-benzotrifluoride of the formula wherein m and n are as defined above with a nitro-phenoxide of the formula where R is defined above, and M is a cation of an alkali metal or an alkaline earth metal.

  式中 m 为 1 至 3 的整数，n 为 1 或 2，R 为氢、羧基、羧酸盐或酯、甲酰基肟、氰基、烷基、烷氧基、氯基、溴基或 N，N-二烷基氨基的二苯醚，是由式中 m 和 n 如上定义的氯-氟-三氟甲苯与式中 R 如上定义的硝基酚和 M 为碱金属或碱土金属的阳离子反应制备的。
• McAdam, David P.; Skerritt, John H., Australian Journal of Chemistry, 1993, vol. 46, # 7, p. 959 - 967
  作者：McAdam, David P.、Skerritt, John H.

  DOI：——

  日期：——
• DE1924972
  申请人：——

  公开号：——

  公开（公告）日：——
• Catalytic pathways in the ethanolysis of fenitrothion, an organophosphorothioate pesticide. A dichotomy in the behaviour of crown/cryptand cation comple×ing agents
  作者：Vimal K. Balakrishnan、Julian M. Dust、Gary W. vanLoon、Erwin Buncel

  DOI：10.1139/cjc-79-2-157

  日期：——

  The rates of displacement of 3-methyl-4-nitrophenoxide ion from the pesticide, fenitrothion, by alkali metal ethoxides in anhydrous ethanol were followed spectrophotometrically. Through product analysis experiments, which included P-31 NMR and GC-MS, as well as spectrophotometric analysis, three reaction pathways were identified: nucleophilic attack at the phosphorus centre, attack at the aliphatic carbon, and a minor SNAr route (less than or equal to7%). Furthermore, a consecutive process was found to occur on the product of attack at the phosphorus centre. For purposes of kinetic treatment, the processes at the aliphatic and aromatic carbon were combined (i.e., the minor SNAr pathway was neglected), and the observed reaction rate constants were dissected into rate coefficients for nucleophilic attack at phosphorus and at aliphatic carbon. Attack at phosphorus was found to be catalyzed by the alkali metal ethoxides in the order KOEt > NaOEt > LiOEt. Catalysis arises from alkali metal ethoxide aggregates in the base solutions used (0-1.8 M); treatment of the system as a mixture of free ethoxide, ion-paired metal ethoxide, and metal ethoxide dimers resulted in a good fit with the kinetic data. An unexpected dichotomy in the kinetic behaviour of complexing agents (e.g., DC-18-crown-6, [2.2.2]cryptand) indicated that the dimers are more reactive than free ethoxide anions, which are in turn more reactive than ion-paired metal ethoxide. The observed relative order of reactivity is explained in the context of the Eisenman theory in which the free energy of association of the metal ion with the rate-determining transition state is largely determined by the solvent reorganization parameter. In contrast with displacement at the phosphorus centre, attack at the aliphatic carbon was not found to be catalyzed by alkali metals. In this case, the free ethoxide anion was more reactive than either the ion-paired metal ethoxide or the dimeric aggregate. The differing effects of alkali metals on the two pathways is ascribed largely to the leaving group pK(a). For carbon attack, the pK(a) value estimated for demethyl fenitrothion, 2.15, is sufficiently low that metal ions are not required to stabilize the rate-determining transition state. In contrast, for phosphorus attack, 3-methyl-4-nitrophenoxide, with a pK(a) of 7.15, requires stabilization by metal ion interactions. Hence, alkali metal ions catalyze attack at phosphorus, but not attack at the carbon centres.
• LOOK M., J. LABELLED COMPOUNDS AND RADIOPHARM., 1978, 15 545-547
  作者：LOOK M.

  DOI：——

  日期：——