二氯碘甲烷 | 594-04-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 中文名称: 二氯碘甲烷
• 英文名称: dichloroiodomethane
• 英文别名: iododichloromethane；Dichloriodmethan；DCIM；dichloro-iodo-methane；Dichlor-jod-methan；Methyljodidchlorid；dichloro(iodo)methane
• CAS: 594-04-7
• 化学式: CHCl₂I
• 分子量: 210.829
• InChiKey: HNLZCOJXSLDGKD-UHFFFAOYSA-N

物化性质

• 沸点：
  132°C (estimate)
• 密度：
  2.3920
• 溶解度：
  丙酮（少量溶解）、氯仿、甲醇（少量溶解）
• 保留指数：
  779;795

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  4
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

制备方法与用途

生物活性：二氯碘甲烷是人体中的一种天然产物。

靶点：人类内源性代谢物

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反应信息

• 作为反应物：
  描述：

  二氯碘甲烷 在 重水 作用下， 生成 dichloro-deuterio-iodo-methane
  参考文献：
  名称：

  The Relative Rates of Formation of Carbanions by Haloforms¹

  摘要：

  DOI：

  10.1021/ja01563a037
• 作为产物：
  描述：

  氯仿 在 氢氧化钾 、 18-冠醚-6 、 sodium iodide 作用下， 以 水 为溶剂， 反应 48.0h， 以30%的产率得到二氯碘甲烷
  参考文献：
  名称：

  Determination, synthesis and survey of iodinated trihalomethanes in water treatment processes

  摘要：

  Trihalomethanes (THMs) are formed as a result of the interaction of free aqueous chlorine, used as a disinfectant in drinking water, with the organic matter in raw water. Although chlorinated, brominated and chlorobromotrihalomethanes are the most common disinfection by-products reported, iodinated trihalomethanes (ITHMs) can be formed when iodide is present in raw water, ITHMs have been usually associated with several medicinal or pharmaceutical taste and odor events in drinking water. For instance, the odor and taste threshold concentrations of iodoform are 0.02 and 5 mu g/l, respectively. Different analytical techniques have been studied to identify these compounds but their quantitative determination has not been performed due to the lack of commercial standards. In this study ITHMs (CHCl2I, CHClI2, CHBr2I, CHBrI2 and CHBrClI) have been synthesized in order to evaluate headspace (HS), purge and trap (P&T), closed loop stripping analysis (CLSA) and liquid-liquid extraction (LLE) as analytical methods for determination. HS and LLE were followed by gas chromatography and electron capture detector (GC/ECD); whereas P&T and CLSA with gas chromatography and mass spectrometry (GC/MS). The most appropriate method, LLE/GC/ECD, was applied to evaluate the stability of ITHMs in water (ultrapure, raw and treated water) in order to confirm their presence in tap water. Ascorbic acid was the quenching reagent chosen to avoid free chlorine at the time of sample collection. Finally, samples from the different stages of the treatment plant in Barcelona (NE Spain) were analyzed. Only three (CHCl2I, CHBrClI and CHBr2I) of the six ITHMs were identified and determined, at average levels lower than 1 mu g/l, in sand filtered and ozonated waters. No ITHMs were identified in distribution system water. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0043-1354(00)00079-8

文献信息

• Synthesis of monohalocyclopropane derivatives from olefins by the reaction with trihalomethanes and copper
  作者：Nariyoshi Kawabata、Masami Tanimoto、Shigehiro Fujiwara

  DOI：10.1016/0040-4020(79)85049-8

  日期：1979.1

  bromo-, and iodocyclopropane derivatives were obtained in 10–80% yields by the reaction of FCHI2, ClCHI2, BrCHI2, and CHI3, respectively, with Cu in the presence of olefins. The reaction was electrophilic, and proceeded stereospecifically, i.e., cis and trans olefins afforded cyclopropane derivatives whose configurations with respect to the substituents from original olefins were cis and trans, respectively

  在烯烃存在下，通过FCHI 2，ClCHI 2，BrCHI 2和CHI 3分别与Cu反应，可以以10-80％的产率获得氟代，氯代，溴代和碘代环丙烷衍生物。该反应是亲电的，并且立体定向地进行，即，顺式和反式烯烃提供环丙烷衍生物，其相对于来自原始烯烃的取代基的构型为顺式和反式。， 分别。由于在反应混合物中未检测到异构烯烃，这是通过将相应的游离单卤代碳烯插入CH键所预期的，因此该反应似乎是通过有机铜中间体而不是游离的单卤代碳烯进行的。关于通过新反应引入的卤素的构型，通常主要在相应的反式或外型异构体上获得顺式或内式异构体。
• Carbene−Bridgehead Olefin−Carbene Rearrangement:  Formation of the Tetracyclo[4.3.0.0^2,8.0^4,7]nonane Skeleton by Carbene CH Insertion¹
  作者：Thomas Ströter、Günter Szeimies

  DOI：10.1021/ja984114a

  日期：1999.8.1

  tetracyclononane derivatives 15 in good yields. The carbenes 6 show only slight preferences in the rearrangement to alkenes 7 and 8. Both could be trapped with α-methylstyrene as ene adducts 16 and 17. The strongly twisted bridgehead olefin 7 has only the option to rearrange to carbene 9, whereas 8 could give 9 or 10, but prefers to give 9, in accordance with results of DFT calculations. The tetracyclononanes 15c

  已经研究了卡宾 6 的重排序列。6 的前体是 1-halo-3-(n-halomethyl)bicyclo[1.1.1]pentane 衍生物 11，它是通过将多卤甲烷加成到 [1.1.1]propellane 衍生物 13 的中心键通过自由基链过程获得的。化合物 11 与 MeLi 或双（三甲基甲硅烷基）酰胺钠反应生成卡宾 6，通过卡宾 (6)-桥头烯烃-卡宾 (9) 重排稳定，然后卡宾 9 的分子内 CH 插入反应得到四环壬烷衍生物15 收益率良好。卡宾 6 在重排为烯烃 7 和 8 时仅表现出轻微的偏好。两者都可以作为烯加合物 16 和 17 被α-甲基苯乙烯捕获。强烈扭曲的桥头烯烃 7 只能选择重排为卡宾 9，而 8 可以给 9 或 10，但根据 DFT 计算的结果，更愿意给出 9。四环壬烷 15c 和 15d 在 1,3-位含有卤原子；在治疗...
• IR spectroscopic study of the dichloromethyl peroxyl radical and its deuterated analogs in the argon matrix
  作者：E. G. Baskir、O. M. Nefedov

  DOI：10.1007/s11172-021-3339-4

  日期：2021.11

  The dichloromethyl peroxyl radical (CHCl2OO•) and its deuterated analog formed in the reaction of the corresponding dichloromethyl radicals with O2 were studied by matrix IR spectroscopy. Dichloromethyl radicals are generated by the pyrolysis of the corresponding dichloromethyl iodides. The previously known spectral data are supplemented by an information about the peroxyl fragment vibrations, and

  通过基质红外光谱研究了相应的二氯甲基自由基与O 2反应形成的二氯甲基过氧自由基(CHCl 2 OO • )及其氘代类似物。二氯甲基自由基是通过相应的二氯甲基碘化物的热解产生的。先前已知的光谱数据由有关过氧化氢碎片振动的信息补充，并且在 1100.2 cm -1处的未识别带可靠地分配给OO键的伸缩振动。它在同位素取代自由基 CHCl 2 18 O 18 O的光谱中移动到 1040.6 cm -1 •被观察到。首次获得了氘取代基CDCl 2 OO •的红外光谱。研究了光气和甲酰氯形成过程中所研究的自由基的光解过程。
• The photoinduced reaction of 2-iodothiophene in solutions of n-heptane, dichloromethane and methanol
  作者：O. S. Herrera、J. D. Nieto、A. C. Olleta、S. I. Lane

  DOI：10.1002/poc.1769

  日期：2011.5

  The photoinduced reaction of 2‐iodothiophene in n‐heptane, dichloromethane and methanol was studied at room temperature from experiments carried out with degassed solutions. The photoproducts of the reaction were mainly thiophene and small amounts of iodine in all three solvents used. The concentration of 2‐iodothiophene decreases throughout photolysis, following a first‐order rate law and the pseudo‐first‐order

  在室温下，通过脱气溶液进行的实验研究了2-碘噻吩在正庚烷，二氯甲烷和甲醇中的光诱导反应。在所有使用的三种溶剂中，反应的光产物主要是噻吩和少量的碘。遵循一级速率定律，在整个光解过程中2-碘噻吩的浓度降低，并且在所用的三种溶剂中确定了伪一级速率常数。对系统的光化学进行定量，确定n中2-碘噻吩消耗和噻吩形成的量子产率庚烷溶液。结果表明，在本研究的实验条件下，观察到仅源自噻吩基自由基反应的产物。为支持实验结果，计算了噻吩基的电离电势，碘原子的电子亲和力以及在使用的不同溶剂中相应碘化物和碳阳离子的溶剂化自由能。版权所有©2010 John Wiley＆Sons，Ltd.
• A New Organocobalt Complex Containing a Co−N−C Three Membered Ring
  作者：Renata Dreos、Alessandro Felluga、Giorgio Nardin、Lucio Randaccio、Patrizia Siega、Giovanni Tauzher

  DOI：10.1021/ic010418d

  日期：2001.10.1

  complex to form the C-N bond of the metallocycle. Kinetic studies of the formation of this novel complex starting from [(XCH(2)Co(III)(LNH-py)(HLNH-py)](+) (X = Cl,Br,I) showed that the metallocycle formation rates increase in the order Cl < Br < I. Kinetic data are consistent with a mechanism involving an intermediate species resulting from the deprotonation of an amine equatorial nitrogen in a rapid preequilibrium

  处理[RCo（III）（LNH-py）（HLNH-py）]（+）类型的R = -CH（2）X（X =卤素）衍生物，其中HLNH-py = 2-（2-吡啶基-乙基）氨基-3-丁酮肟和LNH-py的共轭碱与稀NaOH的结合，通过一种途径将新的配合物包含三元环，该途径涉及将赤道氮供体分子内亲核加成到轴向碳上。X射线分析显示结构高度失真。C-Co-N角为锐角（42.8度），配位球的变形集中在Co-C轴向键和Co-N键中，这些键移离CH（2）X母体中的伪八面体位置配合物形成金属环的CN键。从[（XCH（2）Co（III）（LNH-py）（HLNH-py）]（+）（X = Cl，Br，