1,2-二甲基咪唑 | 1739-84-0

• 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: 1,2-二甲基咪唑
• 中文别名: 1,2-二甲基-1H-咪唑；1,2-二甲咪唑；N,2-二甲基咪唑
• 英文名称: 1,2-dimethyl-1H-imidazole
• 英文别名: 1,2-dimethylimidazole
• CAS: 1739-84-0
• 化学式: C₅H₈N₂
• mdl: MFCD00005294
• 分子量: 96.1319
• InChiKey: GIWQSPITLQVMSG-UHFFFAOYSA-N

物化性质

• 熔点：
  37-39 °C (lit.)
• 沸点：
  204 °C (lit.)
• 密度：
  1.084 g/mL at 25 °C (lit.)
• 闪点：
  198 °F
• LogP：
  0.11 at 25℃
• 物理描述：
  Liquid; OtherSolid
• 保留指数：
  1006;1006
• 稳定性/保质期：
  在常温常压下保持稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险等级：
  8
• 安全说明：
  S2,S24,S26
• 危险品运输编号：
  UN 3263 8/PG 2
• WGK Germany：
  2
• 海关编码：
  29332990
• 危险类别：
  8
• 危险品标志：
  Xi
• 危险类别码：
  R22,R41,R38
• RTECS号：
  NI4838854
• 包装等级：
  III
• 危险性防范说明：
  P501,P260,P270,P264,P280,P303+P361+P353,P301+P330+P331,P363,P301+P312+P330,P304+P340+P310,P305+P351+P338+P310,P405
• 危险性描述：
  H302,H314
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥的地方。

SDS

Name:	1 2-Dimethylimidazole 98% Material Safety Data Sheet
Synonym:	None
CAS:	1739-84-0

Section 1 - Chemical Product MSDS Name:1 2-Dimethylimidazole 98% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1739-84-0	1,2-Dimethylimidazole	98	217-101-2

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Combustible liquid and vapor.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Remove all sources of ignition. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Discard contaminated shoes.
Do not breathe dust. Keep away from heat and flame.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Corrosives area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1739-84-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Chunks
Color: clear to white
Odor: None reported.
pH: Not available.
Vapor Pressure: 1 mmHg @ 20 C
Viscosity: Not available.
Boiling Point: 204 deg C
Freezing/Melting Point: 29 - 30 deg C
Autoignition Temperature: 480 deg C ( 896.00 deg F)
Flash Point: 92 deg C ( 197.60 deg F)
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water: soluble in organic solvents
Specific Gravity/Density: 1.080 g/cm3
Molecular Formula: C5H8N2
Molecular Weight: 96.13

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Ignition sources, dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1739-84-0: NI4838854 LD50/LC50:
Not available.
Carcinogenicity:
1,2-Dimethylimidazole - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: CORROSIVE SOLID, N.O.S.*
Hazard Class: 8
UN Number: 1759
Packing Group: II
IMO
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing Group: II
RID/ADR
Shipping Name: CORROSIVE SOLID, N.O.S.
Hazard Class: 8
UN Number: 1759
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 24 Avoid contact with skin.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
WGK (Water Danger/Protection)
CAS# 1739-84-0: No information available.
Canada
CAS# 1739-84-0 is listed on Canada's DSL List.
CAS# 1739-84-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1739-84-0 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

合成方法

向500mL三口烧瓶中加入128g 2-甲基咪唑和100mL乙二醇单甲醚。油浴加热至120℃，在该温度下滴加320g碳酸二甲酯。控制反应温度在120～125℃范围内，并确保滴加时间维持7～8小时。滴加完毕后，在130℃条件下保温3小时。保温结束后，通过气相色谱分析确认2-甲基咪唑的转化率为76%。

随后，在4.0KPa、60℃条件下进行减压蒸馏，以蒸发除去溶剂。使用精馏装置，在4.0KPa真空度下收集100～110℃范围内的馏分，即可得到高纯度的1,2-二甲基咪唑成品，其收率为72%，经气相色谱分析含量达到99.0%。

化学性质

1,2-二甲基咪唑为白色棱状结晶，熔点为29-30℃，密度为1.0800，沸点为204℃。

用途

1,2-二甲基咪唑主要用作环氧树脂和其它树脂的固化剂、医药中间体。此外，它还可用作研究用缓冲液、固化剂及有机合成中的原料。

反应信息

• 作为反应物：
  描述：

  1,2-二甲基咪唑 以 乙腈 为溶剂， 反应 96.58h， 生成 1-allyl-2,3-dimethylimidazolium trifluoromethanesulfonate
  参考文献：
  名称：

  同时合成两种离子液体的通用方法，否则难以获得，具有高原子经济性。

  摘要：

  提出了一种新的合成方法以及具有烯丙基或乙基取代基以及三氟甲磺酸根，甲苯磺酸根，硫酸甲酯或甲磺酸根阴离子的氮基离子液体的全光谱（NMR，IR，MS）和离子色谱表征（IC）。在16种新型离子液体的样品上，已证明了阴离子交换方法的多功能性。在已经进行的复分解反应中，使用烷基化剂将卤化物阴离子在离子液体中与基于烷基磺酸盐的阴离子交换。讨论了使用离子色谱分析新合成的化合物获得的结果。另外，还提出了利用在易位反应中获得的气态卤代甲烷副产物的利用方法，否则该副产物难以合成。这种方法确保了整个过程的高原子经济性，

  DOI：

  10.1002/open.201900217
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 磷化氢 、 氢碘酸 作用下， 生成 1,2-二甲基咪唑
  参考文献：
  名称：

  Balaban; Pyman, Journal of the Chemical Society, 1924, vol. 125, p. 1569

  摘要：

  DOI：
• 作为试剂：
  描述：

  胡椒酸 在 1,2-二甲基咪唑 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,3-Bis-benzo[1,3]dioxol-5-yl-[1,3]diazetidine-2,4-dione
  参考文献：
  名称：

  Inhibition of serine proteases: activity of 1,3-diazetidine-2,4-diones

  摘要：

  The present work demonstrates that the 1,3-diazetidifie-2,4-dione nucleus is effective as a scaffold of serine protease inhibitors. Compound 1 displayed high activity against human cathepsin G and alpha -chymotrypsin (0.39, 0.69 nM). Compound 6 exhibited 0.85 nM inhibition of human chymase. Compound 10 was a selective inhibitor against human neutrophil elastase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00264-5

文献信息

• Supported Ionic Liquids. New Recyclable Materials for theL-Proline-Catalyzed Aldol Reaction
  作者：Michelangelo Gruttadauria、Serena Riela、Carmela Aprile、Paolo Lo Meo、Francesca D'Anna、Renato Noto

  DOI：10.1002/adsc.200505227

  日期：2006.1

  New materials for L-proline recycling have been developed. These materials have been applied to the L-proline-catalyzed aldol reaction between acetone and several aldehydes. The L-proline has been supported on the surface of modified silica gels with a monolayer of covalently attached ionic liquid with or without additional adsorbed ionic liquid. Good yields and ee values, comparable with those obtained

  已经开发出用于L-脯氨酸再循环的新材料。这些材料已被用于丙酮和几种醛之间的L-脯氨酸催化的羟醛反应。L-脯氨酸已通过共价键合的离子液体单层负载在改性硅胶的表面上，带有或不带有其他吸附离子液体。与咪唑啉鎓修饰的和4-甲基吡啶鎓修饰的硅胶相比，已经获得了与在均相条件下获得的产率和ee值相当的良好产率和ee值。此外，这些材料已经可以通过简单的过滤容易地回收，并且已经对其再利用进行了研究。这些研究表明，这些材料至少可以使用七次。最后，对于咪唑啉鎓改性的硅胶，
• Imidazolium ion tethered TsDPENs as efficient water-soluble ligands for rhodium catalyzed asymmetric transfer hydrogenation of aromatic ketones
  作者：Guowei Kang、Silong Lin、Atul Shiwakoti、Bukuo Ni

  DOI：10.1016/j.catcom.2014.08.006

  日期：2014.12

  TsDPEN has been synthesized readily and used as a water-soluble ligand for [Cp*RhCl2]2 catalyzed asymmetric transfer hydrogenation (ATH) of aromatic ketones in water. This process provided the secondary alcohols in moderate to excellent conversions (up to 100%) with high enantioselectivities (up to 98% ee) under mild reaction conditions without adding any surfactants. The catalytic system is highly effective

  咪唑离子束缚的TsDPEN易于合成，并用作[Cp * RhCl 2 ] 2催化的水中芳族酮的不对称转移氢化（ATH）的水溶性配体。该方法在温和的反应条件下，无需添加任何表面活性剂即可提供中等至极好的转化率（最高100％）和高对映选择性（最高98％ee）的仲醇。底物与催化剂（S / C）之比为500，低氢化物供体负载为1.5当量，该催化体系非常有效。HCO 2 Na的含量。所介绍的过程很简单，使该方法适合实际使用。
• Imidazolium-containing diselenides for catalytic oxidations with hydrogen peroxide and sodium bromide in aqueous solutions
  作者：Eduardo E. Alberto、Antonio L. Braga、Michael R. Detty

  DOI：10.1016/j.tet.2012.08.004

  日期：2012.12

  The design and synthesis of imidazolium-containing diselenides 4a–c is described. The introduction of the N-methylimidazolium group gives freely soluble compounds in water, unlike the majority of common organic diselenides. Catalytic amounts of 4a–c effectively promote bromination of organic substrates using a safe and inexpensive NaBr/H2O2 system in water. Kinetics experiments revealed that the bromination

  描述了含咪唑鎓二硒化物4a – c的设计与合成。与大多数常见的有机二硒化物不同，N-甲基咪唑鎓基团的引入可在水中提供可自由溶解的化合物。使用安全和廉价的NaBr / H 2 O 2水溶液，催化量的4a – c可有效促进有机底物的溴化。动力学实验表明，4-戊烯酸的溴化反应对NaBr和H 2 O 2都具有一级依赖性浓度反应速率也对溶液的pH敏感。制备反应表明，与4a相比，二苯基二硒化物5是不良的催化剂，离子液体溴化1-苄基-3-甲基咪唑鎓溴化物6没有与H 2 O 2的催化活性，表明结合的官能团具有协同作用。
• [EN] BICYCLIC INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS BICYCLIQUES DE L'HISTONE DÉSACÉTYLASE
  申请人：RODIN THERAPEUTICS INC

  公开号：WO2020014602A1

  公开（公告）日：2020-01-16

  Provided herein are compounds of Formula I and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with histone deacetylases (HDAC).

  本文提供了公式I的化合物及其药用盐和组合物，这些化合物对治疗与组蛋白去乙酰化酶（HDAC）相关的各种疾病条件有用。
• Synthesis of chiral iron-based ionic liquids: modelling stable hybrid materials
  作者：Carmen Martin、Israel Cano、Fabio Scé、Rubén Pérez-Aguirre、Carolina Gimbert-Suriñach、Pilar Lopez-Cornejo、Imanol de Pedro

  DOI：10.1039/d0nj00349b

  日期：——

  iron-containing ionic liquids were synthetized from several chiral ionic liquids (CILs) based on different imidazolium cations. These novel compounds were prepared through an easy synthetic method involving mixing 1 equivalent of iron salt FeX3 (X = Cl or Br) and 1 equivalent of chiral ionic liquid. The so-obtained chiral iron-based ionic liquids contain easily tunable imidazolium cations, which allow

  基于不同的咪唑阳离子，由几种手性离子液体（CIL）合成了五种手性铁离子液体。这些新型化合物是通过一种简单的合成方法制备的，该方法包括混合1当量的铁盐FeX 3（X = Cl或Br）和1当量的手性离子液体。如此获得的手性铁基离子液体包含易于调节的咪唑鎓阳离子，其允许在不同的官能团和手性部分中制备多种化合物。这些手性铁基离子液体已通过多种技术进行了全面表征，包括极化测定法，电感耦合等离子体发射光谱法，元素分析，热重分析，差示扫描量热法，磁化率测量以及紫外线可见光，衰减全反射傅立叶变换红外光谱和拉曼光谱。这样的实验证实了这些新材料的结构以及它们的吸引力。IL结构内的手性部分与卤代草酸根阴离子的结合允许形成具有前景的手性，磁性，光学和酸性性质的非常稳定和多功能的化合物。所得的基于手性铁的ILs具有广泛的应用潜力，例如对映选择性催化或手性识别等。

表征谱图