4-碘-2-甲基-1H-咪唑 | 73746-45-9

• 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: 4-碘-2-甲基-1H-咪唑
• 中文别名: 4-碘-2-甲基-咪唑；2-甲基-4(5)-碘-1(h)-咪唑
• 英文名称: 5-iodo-2-methyl-1H-imidazole
• CAS: 73746-45-9
• 化学式: C₄H₅IN₂
• mdl: MFCD02684335
• 分子量: 208.002
• InChiKey: SEDSLMWYUQACGR-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C
• 沸点：
  358.2±15.0 °C(Predicted)
• 密度：
  2.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  应存于室温、密封、干燥处。

SDS

Name:	4-Iodo-2-methyl-1h-imidazole 97% Material Safety Data Sheet
Synonym:
CAS:	73746-45-9

Section 1 - Chemical Product MSDS Name:4-Iodo-2-methyl-1h-imidazole 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
73746-45-9	4-Iodo-2-methyl-1H-imidazole	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. 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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 73746-45-9: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 139 - 141 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C4H5IN2
Molecular Weight: 208

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen iodide, iodine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 73746-45-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Iodo-2-methyl-1H-imidazole - Not listed by ACGIH, IARC, or NTP.

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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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 73746-45-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 73746-45-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 73746-45-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-碘-2-甲基-1H-咪唑 在 甲醇 、 sodium tetrahydroborate 、 Pd/AlO(OH) 、 水 作用下， 反应 1.5h， 以95%的产率得到2-甲基咪唑
  参考文献：
  名称：

  使用异质Pd / AlO（OH）纳米粒子和硼氢化钠对卤代芳烃进行实用且高效的还原脱卤

  摘要：

  芳基卤化物的还原性脱卤是通过使用市售的氢氧化铝负载的钯（Pd / AlO（OH））纳米粒子与硼氢化钠进行的，纳米粒子的尺寸约为3 nm（Pd的重量百分比为0.5 wt。％）。在室温下超声条件下，在H 2 O / MeOH（v / v = 1/1）的混合物中进行绝对转化，得到脱卤产物。在1.5–4小时内，所有芳基卤化物都成功转化为无卤素化合物，收率超过95％。一锅催化法是一种新的卤代化合物还原脱卤方法。该方法非常简单，高效且环保，回收率极高。

  DOI：

  10.1016/j.tet.2016.08.027
• 作为产物：
  描述：

  2-甲基咪唑 在 potassium iodide 、 sodium hydroxide 、 溶剂黄146 、 sodium sulfite 作用下， 以 水 、 甲醇 、 乙醇 为溶剂， 反应 52.0h， 以91%的产率得到4-碘-2-甲基-1H-咪唑
  参考文献：
  名称：

  含 IDO1 的咪唑异吲哚衍生物的晶体结构揭示了吲哚胺 2,3-双加氧酶 1 (IDO1) 抑制剂设计中的重要氢键网络

  摘要：

  吲哚胺 2,3-双加氧酶 1 (IDO1) 可促进肿瘤的免疫逃逸，是癌症免疫疗法的治疗靶点。已经确定了许多 IDO1 抑制剂，但只有有限的 IDO1 抑制剂结构生物学研究可用于提供对 IDO1 结合机制的见解。在这项研究中，我们展示了 IDO1 与24复合物的结构，24是一种具有有效活性的 NLG919 类似物。复杂的结构揭示了24的咪唑氮原子与血红素铁配位，咪唑异吲哚核位于口袋 A，1-环己基乙醇部分延伸到口袋 B 与周围的残基相互作用。最有趣的是，24与 IDO1 形成广泛的氢键网络，这是 IDO1/ 24复合结构的显着特征，在其他 IDO1 复合结构中未观察到。24的几种类似物的进一步构效关系、紫外光谱和结构生物学研究表明，广泛的疏水相互作用和独特的氢键网络有助于咪唑异吲哚衍生物的强大效力。这些结果有望促进新型 IDO 抑制剂的基于结构的药物设计。

  DOI：

  10.1021/acs.jmedchem.5b01390
• 作为试剂：
  描述：

  6-trimethylstannyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide 、 4-碘-2-甲基-1H-咪唑 、 三(2-呋喃基)膦 在 Pd(dibenzylideneacetone)₂ 4-碘-2-甲基-1H-咪唑 、 Pd(dibenzylideneacetone)₂ 、 三(2-呋喃基)膦 、 甲醇 、 二氯甲烷 、 silica 、 expected product 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以to give 28 mg of 6-(2-methyl-1H-imidazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a beige-coloured solid的产率得到6-(2-methyl-1H-imidazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide
  参考文献：
  名称：

  6-heterocyclic-imidazo[1,2-α]pyridine-2-carboxamide derivatives, preparation and therapeutic use thereof

  摘要：

  公式（I）的化合物： 其中，X，R1，R2，R3和R4如本文所定义，或其酸加成盐；以及它们的治疗用途。

  公开号：

  US08314109B2

文献信息

• Heteroaryl-substituted imidazole derivatives
  申请人：——

  公开号：US20040254179A1

  公开（公告）日：2004-12-16

  The present invention relates to imidazole derivatives of the general formula 1 wherein R 1 , R 2 , R 3 and R 4 are described hereinbelow. These compounds can be used in the treatment or prevention of mGluR5 receptor mediated disorders. These compounds are useful, interalia, in the treatment or prevention of acute and/or chronic neurological disorders such as psychosis, epilepsy, schizophrenia, Alzheimer's disease, cognitive disorders and memory deficits, as well as chronic and acute pain.

  本发明涉及一般式1的咪唑衍生物，其中R1、R2、R3和R4如下所述。这些化合物可用于治疗或预防mGluR5受体介导的疾病。这些化合物在治疗或预防急性和/或慢性神经系统疾病，如精神病、癫痫、精神分裂症、阿尔茨海默病、认知障碍和记忆缺陷，以及慢性和急性疼痛方面是有用的。
• [EN] IMIDAZOL-4-YL-ETHYNYL-PYRIDINE DERIVATIVES<br/>[FR] DERIVES DE L'IMIDAZOL-4-YL-ETHYNYL-PYRIDINE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004080998A1

  公开（公告）日：2004-09-23

  4-[1-Aryl-imidazol-4-ylethynyl]-2-alkyl-pyridine and 1-heteroaryl-imidazol-4-ylethynyl]-2-alkyl-pyridine derivatives and pharmaceutically acceptable salts thereof for the treatment or prevention of disorders mediated full or in part by metabotropic glutamate receptor 5, e.g. acute, traumatic and chronic degenerative processes of the nervous system, such as Alzheimer's disease, senile dementia, Parkinson's disease, Huntington's chorea, amyotrophic lateral sclerosis and multiple sclerosis, psychiatric diseases such as schizophrenia and anxiety, depression, pain and drug dependency.

  4-[1-芳基-咪唑-4-基乙炔基]-2-烷基吡啶和1-杂环芳基-咪唑-4-基乙炔基]-2-烷基吡啶衍生物及其药用可接受盐，用于治疗或预防由代谢型谷氨酸受体5完全或部分介导的疾病，例如神经系统的急性、创伤性和慢性退行性过程，如阿尔茨海默病、老年性痴呆、帕金森病、亨廷顿舞蹈症、肌萎缩侧索硬化和多发性硬化，精神疾病如精神分裂症和焦虑、抑郁、疼痛和药物依赖。
• [EN] C3-CARBON LINKED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN DEGRADATION<br/>[FR] DÉGRONIMÈRES DE TYPE GLUTARIMIDE LIÉS AU CARBONE C3 POUR LA DÉGRADATION DE PROTÉINES CIBLES
  申请人：C4 THERAPEUTICS INC

  公开号：WO2017197046A1

  公开（公告）日：2017-11-16

  This invention provides Degronimers that have carbon-linked E3 Ubiquitin Ligase targeting moieties (Degrons), which can be linked to a targeting ligand for a protein that has been selected for in vivo degradation, and methods of use and compositions thereof as well as methods for their preparation.

  这项发明提供了一种Degronimers，它具有碳连接的E3泛素连接酶靶向基团（Degrons），可以与一个靶向配体相连，该配体针对的是在体内被选为降解的蛋白质，以及它们的使用方法和组成，以及它们的制备方法。
• Rhodium(III)-Catalyzed Selective Direct Olefination of Imidazoles
  作者：Haoqiang Zhao、Jianbin Xu、Changjun Chen、Xin Xu、Yixiao Pan、Zongyao Zhang、Huanrong Li、Lijin Xu

  DOI：10.1002/adsc.201701515

  日期：2018.3.1

  chelation‐assisted highly regio‐ and stereoselective direct olefination of imidazoles with olefins has been developed. A broad range of C2‐substituted N‐(2‐pyrimidyl)imidazoles underwent smooth C5‐olefination with both activated and unactivated olefins to furnish the corresponding products in good to excellent yields with high tolerance of functional groups on both coupling partners in the presence of a

  已经开发了铑（III）催化的螯合辅助的咪唑与烯烃的高度区域和立体选择性直接烯烃化反应。广泛的C2取代的N-（2-嘧啶基）咪唑在活化和未活化的烯烃下均进行了平滑的C5烯烃化反应，从而以较高的收率提供了相应的产品，并且在存在偶合剂的情况下，两个偶合伙伴对官能团的耐受性都很高阳离子铑（III）催化剂。催化量的Cu（OAc）2（醋酸铜（II））和O 2的组合（氧气）作为末端氧化剂。该方案强烈依赖于使用2-取代的咪唑作为底物，并且发现易于安装和移动的嘧啶导向基团的存在对催化至关重要。机理研究表明，五元罗丹环是催化循环的关键中间体。该方法还可以扩展到苯并咪唑与烯烃的偶联反应。
• Substituted inmidazoles as bombesin receptor subtype-3 modulators
  申请人：Chen David

  公开号：US20100022598A1

  公开（公告）日：2010-01-28

  Certain novel substituted imidazoles are ligands of the human bombesin receptor and, in particular, are selective ligands of the human bombesin receptor subtype-3 (BRS-3). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of BRS-3, such as obesity, and diabetes.

  某些新型取代咪唑是人类炸弹素受体的配体，特别是人类炸弹素受体亚型-3（BRS-3）的选择性配体。因此，它们对于治疗、控制或预防对BRS-3调节敏感的疾病和紊乱，如肥胖症和糖尿病，具有用处。