1-甲基-1H-吲哚-6-甲腈 | 20996-87-6

• 物质功能分类: 医药中间体 - 吲哚类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-甲基-1H-吲哚-6-甲腈
• 中文别名: 1-甲基吲哚-6-甲腈；1-甲基-6-吲哚甲腈；1-甲基-1H-吲哚-6-碳腈
• 英文名称: 1-methyl-1H-indole-6-carbonitrile
• 英文别名: 6-cyano-1-methylindole；6-Cyan-1-methyl-indol；1-methylindole-6-carbonitrile
• CAS: 20996-87-6
• 化学式: C₁₀H₈N₂
• mdl: MFCD08690254
• 分子量: 156.187
• InChiKey: FOGAAHLMYPQCJG-UHFFFAOYSA-N

物化性质

• 熔点：
  68 °C
• 沸点：
  327.8±15.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险等级：
  6.1
• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  存储条件：2-8℃，请干燥密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Methylindole-6-carbonitrile
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: 1-Methylindole-6-carbonitrile
CAS number: 20996-87-6

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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.
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: C10H8N2
Molecular weight: 156.2

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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

反应信息

• 作为反应物：
  描述：

  1-甲基-1H-吲哚-6-甲腈 在 2,6-二甲基吡啶 、 sodium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 3-[1-(1,3-Benzodioxol-5-yl)-2-[(4-isopropylphenyl)sulfonamido]-2-oxoethyl]-6-cyano-1-methyl-1H-indole
  参考文献：
  名称：

  The design and synthesis of a novel series of indole derived selective ETA antagonists

  摘要：

  Conformational constraint has been used as the key design element in the identification of a series of potent and selective ETA antagonists. The most potent antagonist, 32, (ETA IC50 = 0.55 nM) is 722-fold selective over the ETB receptor, as measured by binding experiments. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00660-6
• 作为产物：
  描述：

  6-溴吲哚 在 1-甲基吡咯烷 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1-甲基-1H-吲哚-6-甲腈
  参考文献：
  名称：

  The design and synthesis of a novel series of indole derived selective ETA antagonists

  摘要：

  Conformational constraint has been used as the key design element in the identification of a series of potent and selective ETA antagonists. The most potent antagonist, 32, (ETA IC50 = 0.55 nM) is 722-fold selective over the ETB receptor, as measured by binding experiments. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00660-6
• 作为试剂：
  描述：

  verticillatine B 、 trifluoroacetaldehyde N-triftosylhydrazone 在 potassium carbonate 、 1-甲基-1H-吲哚-6-甲腈 作用下， 以 二氯甲烷 为溶剂， 以53 %的产率得到3-methyl-1-(3-(2,2,2-trifluoroethyl)-1H-indol-5-yl)butan-1-one
  参考文献：
  名称：

  Catalytic C(sp²)−H Trifluoroethylation of Indoles via Iron‐Carbene Insertion

  摘要：

  摘要通过在生物活性分子的支架上加入氟烷基，可以显著改善其药理特性。然而，通过 C-H 键活化或插入反应将氟烷基直接缝合到芳香化合物上是一项艰巨的任务，因此具有挑战性和高要求。在本文中，我们介绍了一种替代 Friedel-Crafts 烷基化反应的未知策略，即以三氟乙醛 N-triftosylhydrazone为碳烯前体，FeTPPCl 为催化剂，依靠铁（III）催化芳香族化合物的 C-H 活化，并通过铁（III）-碳烯插入吲哚的 C(sp2)-H 键，从而实现吲哚的选择性高效三氟乙基化反应。

  DOI：

  10.1002/ejoc.202301140

文献信息

• NEW AMINOTHIAZOLES AS FBPASE INHIBITORS FOR DIABETES
  申请人：Hebeisen Paul

  公开号：US20090143448A1

  公开（公告）日：2009-06-04

  Compounds of formula (I) as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 to R 3 have the significance given in claim 1 and which can be used in the form of pharmaceutical compositions.

  式(I)的化合物以及其药用可接受的盐和酯，其中R1至R3具有权利要求1中给定的含义，并可用于制成药物组合物。
• Tropylium-promoted Ritter reactions
  作者：Son H. Doan、Mohanad A. Hussein、Thanh Vinh Nguyen

  DOI：10.1039/d1cc02947a

  日期：——

  used to be one of the most powerful synthetic tools to functionalize alcohols and nitriles, providing valuable N-alkyl amide products. However, this reaction has not been frequently used in modern organic synthesis due to its employment of strongly acidic and harsh reaction conditions, which often lead to complicated side reactions. Herein, we report the development of a new method using salts of the

  Ritter 反应曾经是功能化醇和腈的最强大的合成工具之一，可提供有价值的N-烷基酰胺产品。然而，由于该反应采用强酸性和苛刻的反应条件，往往会导致复杂的副反应，因此在现代有机合成中并未经常使用。在此，我们报告了一种使用 tropylium 离子盐促进 Ritter 反应的新方法的开发。这种方法适用于一系列醇和腈底物，使相应的产品具有良好的产率。该反应方案适用于微波和连续流反应器，为有机合成中的进一步应用提供了有吸引力的机会。
• Synthesis of Indoles through Domino Reactions of 2‐Fluorotoluenes and Nitriles
  作者：Jianyou Mao、Zhiting Wang、Xinyu Xu、Guoqing Liu、Runsheng Jiang、Haixing Guan、Zhipeng Zheng、Patrick J. Walsh

  DOI：10.1002/anie.201904658

  日期：2019.8.5

  chemistry, and therefore, novel and efficient approaches to their synthesis are in high demand. Among indoles, 2‐aryl indoles have been described as privileged scaffolds. Advanced herein is a straightforward, practical, and transition‐metal‐free assembly of 2‐aryl indoles. Simply combining readily available 2‐fluorotoluenes, nitriles, LiN(SiMe3)2, and CsF enables the generation of a diverse array of indoles

  吲哚是药物化学中必不可少的杂环，因此，迫切需要新颖有效的合成方法。在吲哚中，2-芳基吲哚被描述为特权支架。本文的高级内容是一种简单，实用且不含过渡金属的2-芳基吲哚化合物组装方法。简单地将容易获得的2-氟甲苯，腈，LiN（SiMe 3）2和CsF结合起来，就可以生成各种各样的吲哚（38例，产率48-92％）。可将一系列取代基引入吲哚骨架的每个位置（C4至C7，以及C2处的芳基），以提供进一步处理的方法。
• Electrochemical C−H Amidation of Heteroarenes with<i>N</i>‐Alkyl Sulfonamides in Aqueous Medium
  作者：Yan Zhang、Zhipeng Lin、Lutz Ackermann

  DOI：10.1002/chem.202004229

  日期：2021.1.4

  The construction of C−N bonds by free radical reactions represents a powerful synthetic approach for direct C−H amidations of arenes or heteroarenes. Developing efficient and more environmentally friendly synthetic methods for C−H amidation reactions remains highly desirable. Herein, metal‐free electrochemical oxidative dehydrogenative C−H amidations of heteroarenes with N‐alkylsulfonamides have been

  通过自由基反应构建C-N键代表了对芳烃或杂芳烃直接C-H酰胺化的强大合成方法。为CH酰胺化反应开发高效且对环境友好的合成方法仍然是非常可取的。在此，杂芳烃与N-烷基磺酰胺的无金属电化学氧化脱氢CHH酰胺化反应已经完成。不含催化剂和化学氧化剂的CHH酰胺化反应范围广，并使用电作为绿色和唯一的氧化剂。各种杂芳烃，包括吲哚，吡咯，苯并呋喃和苯并噻吩，都经过了这种C（sp 2）-H氮化。循环伏安法研究和控制实验为无金属电催化直接生成以氮为中心的自由基提供了证据。
• [EN] HETEROARYL COMPOUNDS FOR KINASE INHIBITION<br/>[FR] COMPOSÉS HÉTÉROARYLE D'INHIBITION DE LA KINASE
  申请人：ARIAD PHARMA INC

  公开号：WO2015195228A1

  公开（公告）日：2015-12-23

  Compounds and pharmaceutical compositions that modulate kinase activity, including mutant EGFR and mutant HER2 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including mutant EGFRand mutant HER2 activity, are described herein.

  调节激酶活性的化合物和药物组合物，包括突变的EGFR和突变的HER2激酶活性，以及与激酶活性相关的疾病和病况的治疗方法、化合物、药物组合物，包括突变的EGFR和突变的HER2活性，均在本文中描述。