2-甲基吡咯 | 636-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-甲基吡咯
• 中文别名: 2-甲基-1H-吡咯
• 英文名称: 2-methyl-1H-pyrrole
• 英文别名: 2-methylpyrrole；2-Methylpyrrol；methylpyrrole
• CAS: 636-41-9
• 化学式: C₅H₇N
• mdl: MFCD02822910
• 分子量: 81.1173
• InChiKey: TVCXVUHHCUYLGX-UHFFFAOYSA-N

物化性质

• 熔点：
  -35.6°C
• 沸点：
  147℃
• 密度：
  0.965
• 闪点：
  47℃
• 溶解度：
  可溶于氯仿、甲醇
• 物理描述：
  Liquid
• 保留指数：
  813;837;812;812

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090
• 包装等级：
  III
• 危险类别：
  3,6.1
• 危险性防范说明：
  P261,P301+P310,P305+P351+P338
• 危险品运输编号：
  1992
• 危险性描述：
  H225,H301,H315,H319,H332,H335
• 储存条件：
  室温和干燥环境

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methyl-1H-pyrrole
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Methyl-1H-pyrrole
CAS number: 636-41-9

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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.
Store in closed vessels, refrigerated.
Storage:

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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
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C5H7N
Molecular weight: 81.1

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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.

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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

产品描述

2-甲基吡咯是一种有机化合物，可用于合成三氟甲基化的苯氮卓并吲哚衍生物。苯氮卓并吲哚衍生物是一类重要的含氮杂环化合物，也是许多药物活性分子的关键骨架，具有作为酶抑制剂、抗癌/抗肿瘤等药理活性。因此，研究和合成这类化合物受到了广泛的关注。

产品用途

2-甲基吡咯属于吡咯类衍生物，可用于有机合成。

反应信息

• 作为反应物：
  描述：

  2-甲基吡咯 在 氢气 作用下， 以 乙醇 为溶剂， 120.0 ℃ 、5.0 MPa 条件下， 以74 %的产率得到2-甲基吡咯烷
  参考文献：
  名称：

  一种高活性钴催化剂，用于芳香杂环化合物的普加氢和选择性加氢

  摘要：

  鉴定了一种用于芳族 N-、O- 和 S- 杂环选择性加氢的高活性钴催化剂。关键是简单的三组分催化剂合成，允许优化用于嵌入的 N 掺杂碳与要嵌入的金属物种之间的比例。

  DOI：

  10.1002/chem.202300561
• 作为产物：
  描述：

  5-羟基-2-戊酮 在 三氯化铝 、 氨 作用下， 生成 2-甲基吡咯
  参考文献：
  名称：

  Terent'ew et al., Doklady Akademii Nauk SSSR, 1957, vol. 114, p. 1036,1037

  摘要：

  DOI：
• 作为试剂：
  描述：

  7-fluoro-1-methyl-1H-indole 在 吡啶 、 2-甲基吡咯 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 碘苯二乙酸 、 碘 、 二甲基亚砜 作用下， 以 乙基苯 、 氯苯 为溶剂， 155.0 ℃ 、101.33 kPa 条件下， 生成
  参考文献：
  名称：

  CN116969967

  摘要：

  公开号：

文献信息

• Activation Relay on Rhodium-Catalyzed C–H Aminomethylation in Cooperation with Photoredox Catalysis
  作者：Ruixing Liu、Jiaxin Liu、Yin Wei、Min Shi

  DOI：10.1021/acs.orglett.9b01261

  日期：2019.6.7

  A site selective C–H aminomethylation at indole’s C3 position has been achieved by merging rhodium(III)-catalyzed C–H activation and photoredox catalysis in a one-pot manner. An investigation of the mechanistic insights rationalized the essence of the activation relay and the combination mode.

  通过以一锅方式合并铑（III）催化的C–H活化和光氧化还原催化，已实现了吲哚C3位置的位点选择性C–H氨基甲基化。对机械洞察力的研究使激活继电器和组合模式的本质合理化。
• The copper(<scp>ii</scp>)-catalyzed and oxidant-promoted regioselective C-2 difluoromethylation of indoles and pyrroles
  作者：Dong Zhang、Zheng Fang、Jinlin Cai、Chengkou Liu、Wei He、Jindian Duan、Ning Qin、Zhao Yang、Kai Guo

  DOI：10.1039/d0cc03345f

  日期：——

  highly selective C-2 difluoromethylation of indole derivatives was developed by using sodium difluoromethylsulfinate (HCF2SO2Na) as the source of difluoromethyl groups and a Cu(II) complex as the catalyst. Various substrates were well tolerated in this transformation and the desired products were obtained in moderate to good yields. Moreover, the late-stage C-2 difluoromethylation of bioactive molecules

  通过使用二氟甲基亚磺酸钠（HCF 2 SO 2 Na）作为二氟甲基的来源和Cu（II）络合物作为催化剂，开发了一种新颖且高效的吲哚衍生物高选择性C-2二氟甲基化方法。在这种转化中，各种底物都具有良好的耐受性，并且以中等至良好的产率获得了所需的产物。此外，以高收率实现了含有吲哚环的生物活性分子的后期C-2二氟甲基化。通常，该反应具有出色的官能团相容性，广泛的底物范围和出色的C-2选择性。
• Rhodium‐Catalyzed Additive‐Free C−H Ethoxycarbonylation of (Hetero)Arenes with Diethyl Dicarbonate as a CO Surrogate
  作者：Hirotsugu Suzuki、Yumeng Liao、Yuya Kawai、Takanori Matsuda

  DOI：10.1002/ejoc.202100956

  日期：2021.9.21

  as a CO-free and operationally simple protocol. In this reaction, stable and commercially available diethyl dicarbonate serves as a practical alkoxycarbonyl source, and only ethanol and CO2 were produced as byproducts. The utility of this protocol was demonstrated by a gram-scale reaction and the transformation of the ethyl ester moiety.

  吲哚和芳基吡啶与二碳酸二乙酯的无添加剂乙氧基羰基化已被开发为无 CO 且操作简单的协议。在该反应中，稳定且可商购的二碳酸二乙酯作为实用的烷氧基羰基来源，并且仅产生乙醇和CO 2作为副产物。该协议的效用通过克级反应和乙酯部分的转化得到了证明。
• PYRROLE mTORC INHIBITORS AND USES THEREOF
  申请人：Navitor Pharmaceuticals, Inc.

  公开号：US20190389843A1

  公开（公告）日：2019-12-26

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用这些化合物的方法。
• An Acid-Catalyzed Addition and Dehydration Sequence for the Synthesis of Heteroarylated Steroidal Dienes
  作者：Tanner L. Metz、Grace A. Lutovsky、Levi M. Stanley

  DOI：10.1021/acs.joc.7b03045

  日期：2018.2.2

  Additions of heteroarenes to hormone steroids containing an α,β-unsaturated ketone are reported. Additions of a range of electron-rich heteroarene nucleophiles, including indoles, a pyrrole, and a thiophene, to a variety of commercially available steroids and subsequent dehydration formed 3-heteroarylated steroidal dienes in up to 93% yield. This atom-economical reaction sequence occurs under mild

  据报道，杂芳烃添加到含有α，β-不饱和酮的激素类固醇上。将多种电子富集的杂芳烃亲核试剂（包括吲哚，吡咯和噻吩）添加到各种市售类固醇中，随后脱水以高达93％的收率形成了3-杂芳基化的类固醇二烯。这种原子经济的反应顺序是在三氟甲磺酸铋催化下，在温和的反应条件下发生的。

表征谱图