溴碘甲烷 | 557-68-6

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 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: 溴碘甲烷
• 中文别名: 1-溴-1-碘甲烷
• 英文名称: iodobromomethane
• 英文别名: bromoiodomethane；Bromiodmethan；Brom-jod-methan；bromo(iodo)methane
• CAS: 557-68-6
• 化学式: CH₂BrI
• 分子量: 220.835
• InChiKey: TUDWMIUPYRKEFN-UHFFFAOYSA-N

物化性质

• 沸点：
  138-141 °C (lit.)
• 密度：
  2.93 g/mL at 25 °C (lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  3
• 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

安全信息

• 安全说明：
  S26,S36/39
• 危险品运输编号：
  NONH for all modes of transport
• 危险品标志：
  Xi
• 危险类别码：
  R41,R37/38
• WGK Germany：
  3
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P280,P302+P352,P305+P351+P338+P310
• 危险性描述：
  H315,H318,H335
• 储存条件：
  存储条件：2-8℃，避光、干燥且密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Bromoiodomethane
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: Bromoiodomethane
CAS number: 557-68-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: CH2BrI
Molecular weight: 220.8

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide, hydrogen Iodide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

溴碘甲烷可用作有机合成中间体和医药中间体，主要应用于实验室研发和化工生产过程。

反应信息

• 作为反应物：
  描述：

  溴碘甲烷 在 氮气 作用下， 反应 5.0h， 生成 重氮甲烷
  参考文献：
  名称：

  Maier, Guenther; Reisenauer, Hans Peter, Angewandte Chemie, 1986, vol. 98, # 9, p. 829 - 831

  摘要：

  DOI：
• 作为产物：
  描述：

  二溴甲烷 在 反式-双(三苯基膦)合氯化羰基铑(Ⅰ) 碘甲烷 作用下， 反应 2.0h， 生成 溴碘甲烷
  参考文献：
  名称：

  VIII族金属络合物作为烷基卤化物之间卤素交换的催化剂

  摘要：

  几个共同ordinatively不饱和d 6和d 8组VIII金属络合物可用于多种烷基卤化物之间卤素交换反应有效的催化剂。

  DOI：

  10.1039/c39750000418
• 作为试剂：
  描述：

  methyllithium lithium bromide 、 双(2-噻吩基)二硫醚 在 三甲基氯硅烷 、 溴碘甲烷 、 氯化铵 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 2.0h， 以84%的产率得到bis(thiophen-2-ylthio)methane
  参考文献：
  名称：

  溴甲基锂介导的二硫化物对二硫缩醛的化学选择性同系化

  摘要：

  通过添加溴甲基锂，已开发出二硫化物和二硒化物到相应的二硫代和二硒代乙缩醛的高效，化学选择性的同系物。在存在...的情况下，化学选择性被完全保留。

  DOI：

  10.1039/c5cc10280d

文献信息

• 苯乙烯基砜类化合物、其制备方法以及其作为 神经保护剂的应用
  申请人：华夏生生药业(北京)有限公司

  公开号：CN104230770B

  公开（公告）日：2017-11-21

  本申请涉及以从天然蜂胶提取出来的具有神经保护活性的咖啡酸苯乙酯(CAPE)为先导物，根据生物电子等排原理和氢键作用等理论，设计一类砜基团代替酯基团的新分子，其结构见通式I，式中各个基团的定义如权利要求书所述。同时还涉及化合物体外抗氧化能力评价、细胞水平的神经保护活性评价及透过血脑屏障能力评价。活性评价结果表明，合成出的新化合物神经保护活性增强且更易通过血脑屏障，从而成为一种新型治疗神经退行性疾病的神经保护剂。
• Photochemistry of alkyl halides—VII
  作者：Paul J. Kropp、Norbert J. Pienta、Joy A. Sawyer、Richard P. Polniaszek

  DOI：10.1016/s0040-4020(01)92370-1

  日期：——

  The previously observed cyclopropaoation of alkenes by irradiation of diiodomethane (I) in their presence has been studied in more detail and found to be a synthetically useful procedure which is significantly less subject to steric effects than the traditional Simmons-Smith method. The results from photocyclopropanation of a variety of alkenes are summarized in Tables 1 and 3–4. In a number of cases

  先前观察到的通过二碘甲烷的辐射对烯烃的环丙烷化反应（I）的存在，我们对其进行了更详细的研究，发现它是一种合成上有用的方法，与传统的Simmons-Smith方法相比，其受到的空间位阻明显更少。表1和表3-4汇总了各种烯烃的光环丙烷化结果。在许多情况下，光化学程序提供的结果优于Simmons-Smith方法，尤其是使用空间拥挤的烯烃时。环烯烃显示的光环丙烷化相对速率是环大小的函数，类似于Simmons-Smith方法（表5）。然而，与Simmons-Smith方法相比，光环丙烷化反应的相对速率随着双键取代度的增加而稳定增加（表6），其中空间效应抵消了随着取代作用的增加烯烃的亲核性的提高。α碘化建议使用2作为亚甲基转移物质。在溴化锂存在下，将阳离子2捕集，得到溴碘甲烷。
• Chemoselective Homologation–Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (<i>n+1</i>)-Halomethyl-Alkanes
  作者：Margherita Miele、Andrea Citarella、Thierry Langer、Ernst Urban、Martin Zehl、Wolfgang Holzer、Laura Ielo、Vittorio Pace

  DOI：10.1021/acs.orglett.0c02831

  日期：2020.10.2

  The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high

  据报道，将类胡萝卜素和氢化物顺序安装在羰基上，提供了卤代甲基烷基衍生物。尽管在与以碳为中心的亲电子试剂的反应中使用类胡萝卜素作为亲核试剂，sp 3型烷基卤化物仍然是用于选择性一碳同系物的难以捉摸的材料。我们的策略是利用羰基化合物作为起始原料，从而能够均匀地实现高收率和化学控制。该策略是灵活的，不仅限于类胡萝卜素。而且，各种类似碳负离子的物种可以充当亲核试剂，因此使其具有普遍的适用性。
• A Straightforward Homologation of Carbon Dioxide with Magnesium Carbenoids en Route to α-Halocarboxylic Acids
  作者：Serena Monticelli、Ernst Urban、Thierry Langer、Wolfgang Holzer、Vittorio Pace

  DOI：10.1002/adsc.201801614

  日期：2019.3.5

  homologation of carbon dioxide with stable, (enantiopure) magnesium carbenoids constitutes a valuable method for preparing α‐halo acid derivatives. The tactic features a high level of chemocontrol, thus enabling the synthesis of variously functionalized analogues. The flexibility to generate magnesium carbenoids through sulfoxide‐, halogen‐ or proton‐ Mg exchange accounts for the wide scope of the reaction.

  二氧化碳与稳定的（对映纯）镁类胡萝卜素的同系物构成制备α-卤代酸衍生物的一种有价值的方法。该策略具有高水平的化学控制功能，因此可以合成各种功能化的类似物。通过亚砜，卤素或质子镁交换生成镁类胡萝卜素的灵活性，说明了反应的广泛性。
• Hydrofluoromethylation of alkenes with fluoroiodomethane and beyond
  作者：Sandrine M. Hell、Claudio F. Meyer、Sebastiano Ortalli、Jeroen B. I. Sap、Xuanxiao Chen、Véronique Gouverneur

  DOI：10.1039/d1sc03421a

  日期：——

  for the direct hydrofluoromethylation of alkenes is reported for the first time. This straighforward silyl radical-mediated reaction utilises CH2FI as a non-ozone depleting reagent, traditionally used in electrophilic, nucleophilic and carbene-type chemistry, but not as a CH2F radical source. By circumventing the challenges associated with the high reduction potential of CH2FI being closer to CH3I than

  首次报道了烯烃直接氢氟甲基化的方法。这种直接的甲硅烷基自由基介导的反应利用 CH 2 FI 作为非臭氧消耗试剂，传统上用于亲电、亲核和卡宾型化学，但不作为 CH 2 F 自由基源。通过规避与 CH 2 FI的高还原电位比 CF 3 I更接近 CH 3 I相关的挑战，并利用 C-I 键的有利键解离能，我们证明了原料缺电子烯烃被转化在 (Me 3 Si) 3的干预下，由净氢氟甲基化产生的产物蓝色 LED 激活下的 SiH。这种看似简单但功能强大的方法已扩展到一系列（卤）甲基自由基前体，包括 ICH 2 I、ICH 2 Br、ICH 2 Cl 和 CHBr 2 F，以及 CH 3 I 本身；因此后一种试剂能够直接加氢甲基化。这种多功能化学被应用于18 F-、13 C- 和 D- 标记的试剂以及复杂的生物相关烯烃，为药物化学和正电子发射断层扫描中的应用提供了五十多种产品。

表征谱图