2-氯-1-甲基-1H-咪唑 | 253453-91-7

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 2-氯-1-甲基-1H-咪唑
• 中文别名: 2-氯-1-甲基咪唑
• 英文名称: 2-chloro-1-methyl-1H-imidazole
• 英文别名: 2-chloro-1-methylimidazole
• CAS: 253453-91-7
• 化学式: C₄H₅ClN₂
• mdl: MFCD02179531
• 分子量: 116.55
• InChiKey: VSCQFRRKWFQPOA-UHFFFAOYSA-N

物化性质

• 熔点：
  -10℃
• 沸点：
  214.8±23.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2933290090
• 安全说明：
  S26,S36/37/39
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Chloro-1-methyl-1H-imidazole
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Chloro-1-methyl-1H-imidazole
Ingredient name:
CAS number: 253453-91-7

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C4H5ClN2
Molecular weight: 116.5

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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, nitrogen oxides, hydrogen chloride.

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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

应用

2-氯-1-甲基-1H-咪唑是制备咪唑类离子液体的重要有机合成中间体，主要用作树脂固化剂、粘合剂等。此外，它还可应用于浇注、粘接和玻璃钢等领域。

制备方法

将2-氯咪唑与碳酸二甲酯加入反应器中，在200mL微型高压反应釜中进行反应。该反应釜材质为哈氏合金，并配备磁力搅拌器及背压阀，以控制釜内压力。待反应达到预定时间后，通入冷凝水进行降温，放气至常压后过滤除去催化剂。最后，通过减压蒸馏可获得2-氯-1-甲基-1H-咪唑。

反应信息

• 作为反应物：
  描述：

  2-氯-1-甲基-1H-咪唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-bromo-2-chloro-N-methylimidazole
  参考文献：
  名称：

  一锅顺序溴化和Sonogashira交叉偶联对咪唑的高度区域选择性C-5烷基化

  摘要：

  可通过一锅顺序程序轻松制备各种2取代的5-炔基-1 H-咪唑，该程序涉及1，2-二甲基-1 H-咪唑，2-氯-1的高度区域选择性亲电C-5溴化反应-甲基-1 H-咪唑和2-芳基-1-甲基-1 H-咪唑，然后进行有效的钯/铜共催化的Sonogashira型炔基化反应。

  DOI：

  10.1016/j.tetlet.2015.04.094
• 作为产物：
  描述：

  N-甲基咪唑 在 正丁基锂 、 六氯乙烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 以90%的产率得到2-氯-1-甲基-1H-咪唑
  参考文献：
  名称：

  一锅顺序溴化和Sonogashira交叉偶联对咪唑的高度区域选择性C-5烷基化

  摘要：

  可通过一锅顺序程序轻松制备各种2取代的5-炔基-1 H-咪唑，该程序涉及1，2-二甲基-1 H-咪唑，2-氯-1的高度区域选择性亲电C-5溴化反应-甲基-1 H-咪唑和2-芳基-1-甲基-1 H-咪唑，然后进行有效的钯/铜共催化的Sonogashira型炔基化反应。

  DOI：

  10.1016/j.tetlet.2015.04.094
• 作为试剂：
  描述：

  3-甲基-1-苯基吲哚酮 在 sodium hexamethyldisilazane 、 2-氯-1-甲基-1H-咪唑 、 氧气 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以70%的产率得到3-hydroxy-3-methyl-1-phenylindolin-2-one
  参考文献：
  名称：

  α-Heteroarylation of Esters, Lactones, Amides, and Lactams by Nucleophilic Aromatic Substitution

  摘要：

  A mild and efficient alpha-heteroarylation of simple esters and amides was developed via nucleophilic aromatic substitution. The choice of NaHMDS in toluene gave the best results. A tandem a-heteroarylation and hydroxylation protocol using air as the oxidant afforded tertiary alcohols in good yields.

  DOI：

  10.1021/ol060246u

文献信息

• Scalable synthesis of imidazole derivatives
  申请人：Jones K. Todd

  公开号：US20050250948A1

  公开（公告）日：2005-11-10

  Imidazole derivatives, compositions containing them, methods of preparing them, including regioselective scale-up synthetic methods, and methods of using them.

  咪唑衍生物，含有它们的组合物，制备它们的方法，包括选择性区域放大合成方法，以及使用它们的方法。
• [EN] TRIAZINE DERIVATIVES AND THEIR THERAPEUTICAL APPLICATIONS<br/>[FR] DÉRIVÉS DE TRIAZINE ET LEURS APPLICATIONS THÉRAPEUTIQUES
  申请人：ABRAXIS BIOSCIENCE LLC

  公开号：WO2010144338A1

  公开（公告）日：2010-12-16

  The present invention comprises inter alia compounds as shown in formula (I) or a pharmaceutically acceptable salt thereof.

  本发明包括如式(I)所示的化合物及其药学上可接受的盐等。
• A General Method for Suzuki–Miyaura Coupling Reactions Using Lithium Triisopropyl Borates
  作者：Matthias A. Oberli、Stephen L. Buchwald

  DOI：10.1021/ol302063g

  日期：2012.9.7

  Conditions for the Suzuki–Miyaura coupling of lithium triisopropyl borates are reported, as well as a procedure for a one-pot lithiation, borylation, and subsequent Suzuki–Miyaura coupling of various heterocycles with aryl halides. These borate species are much more stable toward protodeboronation than the corresponding boronic acids and can conveniently be stored on benchtop at room temperature.

  报道了三异丙基硼酸锂 Suzuki-Miyaura 偶联的条件，以及各种杂环与芳基卤化物的单锅锂化、硼酸化和随后的 Suzuki-Miyaura 偶联的程序。这些硼酸盐比相应的硼酸对原脱硼更稳定，可以方便地在室温下储存在台式上。
• A new synthesis of chloroheterocycles via metalhalogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents
  作者：Carla Boga、Erminia Del Vecchio、Luciano Forlani、Lilia Milanesi、Paolo Edgardo Todesco

  DOI：10.1016/s0022-328x(99)00363-0

  日期：1999.10

  rapidly produces the corresponding 2-chloro derivatives in high yields through a metalhalogen exchange mechanism. The use of ethyl trichloroacetate can give better results with respect to those obtained with trichloroacetyl chloride, which probably involves dichloroketene formation. The reaction with Grignard reagents is more complex: in fact, 2-benzothiazolylmagnesium chloride with ethyl trichloroacetate

  芳族氮杂杂环的2-lithio衍生物与三氯乙酰基衍生物之间的反应通过金属-卤素交换机理快速高产地产生了相应的2-氯衍生物。与用三氯乙酰氯得到的三氯乙酸乙酯相比，使用三氯乙酸乙酯可以得到更好的结果，三氯乙酰氯可能涉及二氯乙烯的形成。与格氏试剂的反应更加复杂：实际上，2-苯并噻唑基氯化镁与三氯乙酸乙酯或三氯乙酰氯的反应分别生成2-氯苯并噻唑和大量的1,3-苯并噻唑-2-羧酸乙酯或2-苯并噻唑基二氯甲基酮。
• Cationic Multidentate Halogen-Bond Donors in Halide Abstraction Organocatalysis: Catalyst Optimization by Preorganization
  作者：Stefan H. Jungbauer、Stefan M. Huber

  DOI：10.1021/jacs.5b07863

  日期：2015.9.23

  show that the catalytic activity is based on halogen bonding using, e.g., the chlorinated derivatives as reference compounds. On the basis of these studies, halobenzimidazolium organocatalysts were then investigated. Monodentate compounds featured the same trends as the corresponding imidazolium analogues but showed a stronger catalytic activity. In order to prepare bidentate versions which are preorganized

  与在有机催化中牢固建立的氢键相反，卤素键在该领域的应用仍然很少。在此，我们首次展示了阳离子卤素键供体在卤化物提取反应中的催化应用。首先，系统地测试了基于卤代吡啶鎓、卤咪唑鎓和卤化 1,2,3-三唑鎓的催化剂。与吡啶鎓化合物相比，咪唑鎓和三唑鎓盐均显示出有希望的效力。对于基于卤代咪唑鎓的有机催化剂，我们可以证明催化活性基于卤素键合，例如使用氯化衍生物作为参考化合物。在这些研究的基础上，研究了卤代苯并咪唑鎓有机催化剂。单齿化合物与相应的咪唑鎓类似物具有相同的趋势，但表现出更强的催化活性。为了制备预先组织用于阴离子结合的二齿形式，合成了一类新的刚性双（卤代苯并咪唑鎓）化合物并对其进行了结构表征。相应的顺式异构体显示出前所未有的催化效力，可以低至 0.5 mol% 用于 1-氯异色满与甲硅烷基烯醇醚的基准反应。计算证实顺式异构体可能以双齿方式与氯化物结合。各自的反异构体活性较低并且以单齿方式结合卤