二氯硝基甲烷 | 7119-89-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 二氯硝基甲烷
• 英文名称: dichloronitromethane
• 英文别名: Dichlor-nitro-methan；dichloro(nitro)methane
• CAS: 7119-89-3
• 化学式: CHCl₂NO₂
• mdl: MFCD00869305
• 分子量: 129.93
• InChiKey: XUNYLLBGLKGFHO-UHFFFAOYSA-N

物化性质

• 沸点：
  106-107 °C
• 密度：
  2.122 g/cm3
• 溶解度：
  溶于氯仿

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2904909090

制备方法与用途

生物活性方面，二氯硝基甲烷（Dichloronitromethane）属于卤代硝基甲烷类化合物，是饮用水中的一种消毒副产品。

反应信息

• 作为产物：
  描述：

  二氯硝基乙酸乙酯 在 盐酸 作用下， 反应 19.0h， 以15%的产率得到二氯硝基甲烷
  参考文献：
  名称：

  Synthesis of chloro- and dichloronitromethanes

  摘要：

  DOI：

  10.1007/bf00954250

文献信息

• Catalytic insertion of aldehydes into dihalonitroacetophenones via sequential bond scission-aldol reaction-acyl transfer
  作者：Ransheng Ding、Christian Wolf

  DOI：10.1039/c5cc09753c

  日期：——

  A catalytic process that provides dihalogenated nitro alcohols in up to 99% yield and with 100% atom economy is described. In-situ cleavage of dihalonitroacetophenones affords nitronates that undergo Lewis acid...

  描述了一种催化方法，其以高达99％的收率和100％的原子经济性提供二卤代硝基醇。原位裂解二卤代硝基苯乙酮可得到经过路易斯酸的硝酸盐。
• Steinkopf; Kuehnel, Chemische Berichte, 1942, vol. 75, p. 1329
  作者：Steinkopf、Kuehnel

  DOI：——

  日期：——
• Transformation of Chlorinated Aliphatic Compounds by Ferruginous Smectite
  作者：Javiera Cervini-Silva、Richard A. Larson、Jun Wu、Joseph W. Stucki

  DOI：10.1021/es0015592

  日期：2001.2.1

  A series of chlorinated aliphatic compounds (RCl, including carbon tetrachloride (PCM), 1,1,1 -trichloroethane (TCA), 1,1,2,2-tetrachloroethane (TeCA), pentachloroethane (PCA), hexachloroethane (HCA), trichloroethene (TCE), tetrachloroethene (PCE), trichloronitromethane (chloropicrin, CP), and trichloroacetonitrile (TCAN)) was reacted with ferruginuous smectite (sample SWa-1 from The Source Clays Repository), SWa, in aqueous suspension under anoxic conditions. Compounds highly polarizable or sharing substituents that facilitate charge delocalization adsorbed faster by reduced (SWa-R) than by unaltered (SWa-U) clay, indicating stronger dipole-dipole interactions between the substituents and the clay surface and/or hydrating water molecules. The reduction of the clay accelerated RCl adsorption up to 100-fold. Incubations with SWa-R promoted RCl reduction (CP, TCAN) or dehydrochlorination (TeCA and PCA). The reduction of structural Fe catalyzes the transformation of RCl via Bronsted grid Lewis-basic promoted pathways. This study indicates that oxidation state of the structural Fe in SWa greatly alters surface chemistry and has a large impact on clay-organic interactions.
• Identification of Volatile and Extractable Chloroorganics in Rain and Snow
  作者：Krzysztof Laniewski、Hans BorÉn、Anders Grimvall

  DOI：10.1021/es980480i

  日期：1998.12.1

  Organics enriched from samples of rain, snow, and glacier ice were analyzed to determine the chemical structure of the chloroorganic compounds that were most abundant in such media. Gas chromatography with atomic emission detection (GC-AED) was used to provide an overview of the presence of volatile and extractable chloroorganics at four sites in Europe and one site in Antarctica. Real samples and isomer-specific standards were then analyzed by gas chromatography with mass-spectrometric detection (GC-MS) to identify and confirm the structure of the chloroorganics that had been detected in the GC-AED analysis. The results revealed that of the volatile chloroorganics found in the samples, dichloronitromethane, a compound not previously reported to occur in the ambient environment, was often present in the highest concentration (up to 130 ng L-1). Chlorobenzenes were detected mainly as 1,4-dichlorobenzene and minor amounts of 1,3- and 1,2-dichlorobenzene and one isomer of tetrachlorobenzene (1,2,4,5- or 1,2,3,5-tetrachlorobenzene). Chlorinated alkyl phosphates, which were normally responsible for the largest peaks in the chlorine-specific chromatograms of hexane- or ether-extractable compounds, were present as tris(2-chloroethyl)phosphate, tris(1-chloro-2-propyl)phosphate, and one of the isomers bis(1-chloro-2-propyl)(3-chloro-1-propyl)phosphate or bis(1-chloro-2-propyl)(2-chloro-1-propyl)phosphate. All of the chloroorganic compounds mentioned, i.e., dichloronitromethane, chlorobenzenes, and chlorinated alkyl phosphates, were detected at relatively remote sites in the northern hemisphere, whereas only chlorobenzenes were found in a reference sample of snow from Antarctica.
• Transformation of Chloropicrin and 1,3-Dichloropropene by Metam Sodium in a Combined Application of Fumigants
  作者：Wei Zheng、Scott R. Yates、Mingxin Guo、Sharon K. Papiernik、Jung Ho Kim

  DOI：10.1021/jf0498564

  日期：2004.5.1

  Combined application of fumigants is a potential strategy to replace methyl bromide in the control of soil-borne pests. Unfortunately, abiotic and biotic interactions among fumigants restrict some combined application approaches. In this study, the kinetics and mechanisms of reaction between metam sodium (sodium methyidithiocarbamate) and the halogenated fumigants chloropicrin (trichloronitromethane) and 1,3-dichloropropene (1,3-D) were investigated in aqueous solution. For chloropicrin, an extremely rapid oxidation-reduction process occurred in the presence of metam sodium. The second-order rate constant for the reaction between chloropicrin and metam sodium was approximately 2 orders of magnitude greater than that for the reaction between 1,3-D isomers and metam sodium. Transformation of 1,3-D by metam sodium was associated with an aliphatic S(N)2 nucleophilic substitution process. The nucleophilic reaction of cis-1,3-D with metam sodium was significantly faster than that of the trans isomer and was correlated with a lower reaction activation energy for the cis isomer in the transition state. Combining Telone C-35 (65% 1,3-D and 35% chloropicrin) and metam sodium in solution might yield some nucleophilic sulfur species, which played an important role in the dissipation of 1,3-D. The incompatibility of chloropicrin and 1,3-D with metam sodium was also examined in soil under different application scenarios. Simultaneous application of metam sodium with chloropicrin or 1,3-D accelerated the transformation of the two halogenated fumigants, reducing their availability in soil. A sequential strategy for multiple fumigants was developed, which could be applied without the loss of active ingredient that occurs due to the reaction between fumigants. The proposed methodology may enhance pest control while maintaining environmental protection.