一溴二碘甲烷 | 557-95-9

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物
• 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: 一溴二碘甲烷
• 中文别名: 溴代碘甲烷
• 英文名称: bromodiiodomethane
• 英文别名: diiodobromomethane；Bromdiiodmethan；BDIM；bromo-diiodo-methane；Brom-dijod-methan；bromo(diiodo)methane
• CAS: 557-95-9
• 化学式: CHBrI₂
• 分子量: 346.732
• InChiKey: PTGIGXMFLYACDM-UHFFFAOYSA-N

物化性质

• 熔点：
  >49°C (dec.)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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

反应信息

• 作为反应物：
  描述：

  一溴二碘甲烷 在 mercury(II) fluoride 作用下， 反应 1.0h， 以60%的产率得到bromofluoroiodomethane
  参考文献：
  名称：

  CHBrFI，CHClFI和CHBrClI的新型合成方法

  摘要：

  描述了三种制备CHBrFI，CHClFI和CHBrClI外消旋混合物的简便方法。发现氟化汞是在CHI 2 Br（6）和CHI 2 Cl（8）氟化反应中分别生成CHBrFI，CHClFI的有效氟化剂。通过使用五氯化锑作为氯化剂对CHI 2 Br（6）进行氯化，可在方便温和的条件下提供CHBrClI。

  DOI：

  10.1016/s0040-4020(02)00532-x
• 作为产物：
  描述：

  碘仿 在 溴 作用下， 以 四氯化碳 为溶剂， 以52%的产率得到一溴二碘甲烷
  参考文献：
  名称：

  CHBrFI，CHClFI和CHBrClI的新型合成方法

  摘要：

  描述了三种制备CHBrFI，CHClFI和CHBrClI外消旋混合物的简便方法。发现氟化汞是在CHI 2 Br（6）和CHI 2 Cl（8）氟化反应中分别生成CHBrFI，CHClFI的有效氟化剂。通过使用五氯化锑作为氯化剂对CHI 2 Br（6）进行氯化，可在方便温和的条件下提供CHBrClI。

  DOI：

  10.1016/s0040-4020(02)00532-x

文献信息

• Tandem synthesis of aromatic amides from styrenes in water
  作者：Pratima A. Sathe、Aniket S. Karpe、Aniket A. Parab、Babasao S. Parade、Kamlesh S. Vadagaonkar、Atul C. Chaskar

  DOI：10.1016/j.tetlet.2018.06.021

  日期：2018.7

  one-pot synthesis of aromatic amides has been reported from styrenes in the presence of N-bromosuccinimide and iodine by using aqueous ammonia in water. The reaction proceeds through the formation of α-bromoketone as an intermediate in the presence of NBS and water. α-Bromoketone on reaction with iodine forms bromodiiodoketone which on nucleophilic substitution with aqueous ammonia gives aromatic amide. Substituted

  据报道，在N-溴琥珀酰亚胺和碘的存在下，通过在水中使用氨水，苯乙烯可以方便地一锅合成芳族酰胺。该反应通过在NBS和水的存在下形成中间体α-溴酮来进行。与碘反应时，α-溴酮形成溴二碘酮，在被氨水亲核取代后会生成芳香酰胺。以高收率获得具有宽官能团相容性的取代的芳族酰胺。
• Highly Enantioselective Synthesis of 1,2,3-Substituted Cyclopropanes by Using α-Iodo- and α-Chloromethylzinc Carbenoids
  作者：Louis-Philippe B. Beaulieu、Lucie E. Zimmer、Alexandre Gagnon、André B. Charette

  DOI：10.1002/chem.201202528

  日期：2012.11.12

  α‐chlorozinc carbenoids by using a dioxaborolane‐derived chiral ligand. The synthetically useful iodocyclopropane building blocks were derivatized by an electrophilic trapping of the corresponding cyclopropyl lithium species or a Negishi coupling to give access to a variety of enantioenriched 1,2,3‐substituted cyclopropanes. The synthetic utility of this method was demonstrated by the formal synthesis of an

  此，我们报告的对映和非对映选择性形成反式-碘和反式通过使用二氧硼戊环衍生的手性配体从-chlorocyclopropanesα碘-和α-chlorozinc卡宾。可以通过亲电捕集相应的环丙基锂物质或使用Negishi偶联剂衍生出可用于合成的碘代环丙烷结构单元，从而获得各种对映体富集的1,2,3-取代的环丙烷。HIV-1蛋白酶抑制剂的正式合成证明了该方法的合成效用。另外，还研究了相关的立体选择性溴环丙烷化。还介绍了有关卤代碘甲基锌类胡萝卜素相对亲电性的新见解。
• 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。
• Dehmlow, Eckehard V.; Broda, Witold, Chemische Berichte, 1982, vol. 115, # 12, p. 3894 - 3897
  作者：Dehmlow, Eckehard V.、Broda, Witold

  DOI：——

  日期：——
• Determination, synthesis and survey of iodinated trihalomethanes in water treatment processes
  作者：B Cancho

  DOI：10.1016/s0043-1354(00)00079-8

  日期：2000.9.1

  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.