1,3-二甲基咪唑 碘 | 4333-62-4

• 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 - 有机杂环化合物 - 唑类
• 中文名称: 1,3-二甲基咪唑 碘
• 中文别名: 碘化1,3-二甲基咪唑；1,3-二甲基咪唑碘；1,3-二甲基碘化咪唑鎓；1,3-二甲基咪唑碘化物
• 英文名称: 1,3-dimethylimidazolim iodide
• 英文别名: 1,3-dimethylimidazolium iodide；1,3-dimethyl-1H-imidazol-3-ium iodide；dimethylimidazolium iodide；1,3-dimethyl-1H-imidazolium iodide；N,N-dimethylimidazolium iodide；N,N’-dimethylimidazolium iodide；1-methyl-3-methylimidazolium iodide；1,3-bis(methyl)imidazolium iodide；[Mmim]I；DMMI；1,3-dimethylimidazol-1-ium;iodide
• CAS: 4333-62-4
• 化学式: C₅H₉N₂*I
• 分子量: 224.044
• InChiKey: ARSMIBSHEYKMJT-UHFFFAOYSA-M

物化性质

• 熔点：
  84.0 to 89.0 °C
• 最大波长(λmax)：
  226nm(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.15
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  8.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933290090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319
• 储存条件：
  存放于惰性气体中，并避免光照和潮湿（吸湿）。

SDS

1,3-Dimethylimidazolium Iodide
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1,3-Dimethylimidazolium Iodide
5.3

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 1,3-Dimethylimidazolium Iodide
Percent: >98.0%(HPLC)(T)
CAS Number: 4333-62-4
Chemical Formula: C5H9IN2

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
1,3-Dimethylimidazolium Iodide

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Safety glasses. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Crystal- Powder
Form:
Colour: White - Almost white
No data available
Odour:
1,3-Dimethylimidazolium Iodide

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
pH: No data available
Melting point/freezing point:86°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen Iodide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: orl-mus LDLo:1600 mg/kg
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
Reproductive toxicity: No data available
RTECS Number: NJ5038500

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed
1,3-Dimethylimidazolium Iodide

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,3-二甲基咪唑 碘 在 selenium 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以76 %的产率得到2H-咪唑-2-硒酮,1,3-二氢-1,3-二甲基-
  参考文献：
  名称：

  ABTS 自由基阳离子氧化抗甲状腺药物及其硒类似物

  摘要：

  [显示省略]

  DOI：

  10.1016/j.bioorg.2023.106891
• 作为产物：
  描述：

  (1,3-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene)diiodo(pyridine)palladium 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 1,3-二甲基咪唑 碘
  参考文献：
  名称：

  防止Pd–NHC键断裂并从纳米级转换为分子催化系统：胺和温度作为催化剂活化剂

  摘要：

  Pd配合物与N-杂环卡宾（NHC）配体催化的许多反应都是在通常存在偶合剂或弱碱的胺存在下进行的。但是，胺可以通过多种方式与Pd / NHC配合物反应：通过产生不含NHC的活性钯物质，增强分子催化作用，引起催化剂失活或触发无配体催化方式。这项研究深入了解了有效使用胺作为分子Pd / NHC催化活化剂和防止催化体系中Pd-NHC键发生不希望的还原裂解所需的条件。在25–140°C的温度范围内，检测了Pd / NHC配合物与各种胺的反应以及所得氨基配合物的热稳定性。结果表明胺结构和反应温度对催化剂转化的主要影响。特别是，Pd / NHC配合物与脂肪族胺配体的热分解主要导致还原性Pd-NHC键裂解，而在强碱存在下，在25-60°C下，具有伯和仲脂肪族胺配体的配合物的去质子化促进了激活分子Pd / NHC催化。在这些发现的基础上，提出了适用于强碱促进的芳基卤化物和硫醇之间的CS交叉偶联反应的高效Pd

  DOI：

  10.1039/c9cy02041a
• 作为试剂：
  描述：

  1-((E)-2-溴乙烯基)-4-甲氧基苯 、 溴乙酸乙酯 在 Ni(TMHD)₂ 、 四甲基乙二胺 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 1,3-二甲基咪唑 碘 、 magnesium chloride 作用下， 以 N,N-二甲基苯胺 为溶剂， 反应 24.0h， 以23%的产率得到trans-4-(4-methoxyphenyl)-3-butenoic acid ethyl ester
  参考文献：
  名称：

  镍和光氧化还原催化的芳基乙烯基卤化物和未活化的叔烷基溴的双重还原交叉偶联†

  摘要：

  通过光氧化还原/镍双重催化已经实现了芳基乙烯基卤化物和未活化的叔烷基溴化物的新型还原性交叉偶联，以产生具有优异的E-选择性的带有全碳四元中心的乙烯基芳烃衍生物。可以通过使用市售的N，N，N '，N'-四甲基乙二胺（TMEDA）作为末端还原剂来避免化学计量的金属还原剂。

  DOI：

  10.1039/c9cc00768g

文献信息

• Catalytic Metal-free Allylic C–H Amination of Terpenoids
  作者：Wei Pin Teh、Derek C. Obenschain、Blaise M. Black、Forrest E. Michael

  DOI：10.1021/jacs.0c06997

  日期：2020.9.30

  selective replacement of C-H bonds in complex molecules, especially natural products like terpenoids, is a highly efficient way to introduce new functionality and/or couple fragments. Here, we report the development of a new metal-free allylic amination of alkenes that allows the introduction of a wide range of nitrogen functionality at the allylic position of alkenes with unique regioselectivity and no

  选择性替换复杂分子中的 CH 键，尤其是萜类化合物等天然产物，是引入新功能和/或偶联片段的高效方法。在这里，我们报告了一种新的烯烃无金属烯丙基胺化的开发，它允许在烯烃的烯丙基位置引入广泛的氮官能团，具有独特的区域选择性和无烯丙基转座。该反应使用催化量的硒化膦或硒脲形式的硒。简单的磺酰胺和氨基磺酸盐可直接用于反应，无需制备分离的类氮烯前体。我们通过以高产率和区域选择性胺化大量萜类化合物来证明这种转化的效用。
• Sterically driven synthesis of ruthenium and ruthenium–silver N-heterocyclic carbene complexes
  作者：C. Cesari、S. Conti、S. Zacchini、V. Zanotti、M. C. Cassani、R. Mazzoni

  DOI：10.1039/c4dt02747g

  日期：——

  A sterically driven synthetic route from non-bulky silver NHC to novel Ru(NHC) complexes and from bulky Ag(NHC) to unprecedented heterobimetallic Ru–Ag(NHC) complexes is presented.

  通过立体驱动的合成途径，从非臃肿的银NHC到新颖的Ru(NHC)配合物，以及从臃肿的Ag(NHC)到前所未有的异双金属Ru-Ag(NHC)配合物。
• 氮杂环卡宾金属化合物催化的一级醇偶联制备烷烃的方法
  申请人：复旦大学

  公开号：CN113264809B

  公开（公告）日：2022-03-18

  本发明属于过渡金属催化和生物质醇的偶联反应技术领域，具体为一种氮杂环卡宾金属化合物催化的一级醇自偶联以及交叉偶联一步制备烷烃的方法。本发明首先提供用于一级醇偶联制备烷烃的催化剂‑均相氮杂环卡宾金属化合物。本发明以一级醇为反应原料，以碱金属的叔丁醇盐、氢氧化物等其他强碱为碱，以氮杂环卡宾金属化合物为催化剂，以三级醇、苯的类似物或长链烷烃为溶剂，在80至200℃下反应4至24小时，得到对应的烷烃产物。与现有技术相比，本发明方法能够以廉价易得的生物质醇为起始原料，避免使用有毒且稳定性较差的含膦配体，反应选择性和产率均能达到定量，操作简便，仅需简单的后处理可得到高纯度的不同烷烃产物，适合工业放大和应用。
• π-Conjugated Triazenes: Intermediates That Undergo Oxidation and Substitution Reactions
  作者：Enrique Barragan、Alejandro Bugarin

  DOI：10.1021/acs.joc.6b02705

  日期：2017.2.3

  triazenes is herein reported. This observed and unprecedented triazene reactivity gave access to oxidation and substitution reactions. These transformations include successful synthesis of aldehydes, ketones, ethers, and sulfides from readily available organic azides via π-conjugated triazene intermediates. Notably, the afforded adducts were obtained in good yields, at room temperature, and in the absence

  本文报道了对π-共轭三氮烯的新反应性。这种观察到的和空前的三氮烯反应性使人们可以进行氧化和取代反应。这些转变包括通过π共轭三氮烯中间体从容易获得的有机叠氮化物中成功合成醛，酮，醚和硫化物。值得注意的是，在室温下且不存在添加的金属催化剂的情况下，以良好的产率获得了提供的加合物。
• Radical Deoxygenation of Xanthates and Related Functional Groups with New Minimalist N-Heterocyclic Carbene Boranes
  作者：Shau-Hua Ueng、Louis Fensterbank、Emmanuel Lacôte、Max Malacria、Dennis P. Curran

  DOI：10.1021/ol101015m

  日期：2010.7.2

  Minimalist N-heterocyclic carbene boranes 1,3-dimethylimidazol-2-ylideneborane and 2,4-dimethyl-1,2,4-triazol-3-ylideneborane are readily available and have low molecular weights. They exhibit superior performance to first-generation NHC−boranes, providing improved yields in reductions of xanthates and related functional groups.

  极简主义的N-杂环卡宾硼烷1,3-二甲基咪唑-2-亚基硼烷和2,4-二甲基-1,2,4-三唑-3-亚基硼烷很容易获得，并且分子量低。它们表现出优于第一代NHC-硼烷的性能，在减少黄药和相关官能团方面提供了更高的收率。