5-氯吲哚-2-羧酸甲酯 | 87802-11-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 5-氯吲哚-2-羧酸甲酯
• 英文名称: methyl 5-chloroindole-2-carboxylate
• 英文别名: methyl 5-chloro-1H-indole-2-carboxylate
• CAS: 87802-11-7
• 化学式: C₁₀H₈ClNO₂
• mdl: MFCD04972050
• 分子量: 209.632
• InChiKey: WGAOEHZSJWVLBY-UHFFFAOYSA-N

物化性质

• 保留指数：
  1875

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Chloroindole-2-carboxylic acid methyl ester
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: 5-Chloroindole-2-carboxylic acid methyl ester
CAS number: 87802-11-7

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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: C10H8ClNO2
Molecular weight: 209.6

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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, hydrogen chloride.

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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：

  5-氯吲哚-2-羧酸甲酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以95%的产率得到5-氯-1H-吲哚-2-碳酰肼
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel trifluoromethyl indoles as potent HIV-1 NNRTIs with an improved drug resistance profile

  摘要：

  一系列三氟甲基吲哚类化合物已被设计、合成并进行了抗HIV-1活性评价。

  DOI：

  10.1039/c3ob42186d
• 作为产物：
  描述：

  (Z)-methyl 2-[(4-chlorophenyl)amino]-3-(dimethylamino)acrylate 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以61%的产率得到5-氯吲哚-2-羧酸甲酯
  参考文献：
  名称：

  通过烯胺酮的分子内 Friedel-Crafts 杂环化反应区域选择性和多功能合成吲哚

  摘要：

  描述了一种合成取代的吲哚 5 的新方法，通过路易斯酸催化的烯胺酮 6a-h 的分子内和区域选择性 Friedel-Crafts 环化。通过在热或微波 (MW) 辐射条件下用 DMFDMA 处理，由 2-苯胺基羰基化合物 7 制备化合物 6。从化合物 7 开始并通过 MW 辐射促进了吲哚 5 的替代和较短的一锅两步合成，包括难以捉摸的 2-乙酰吲哚 5i-m。

  DOI：

  10.1055/s-2006-933135

文献信息

• [EN] ARYLAMINOMETHYL PROPENYL BENZHYDROXYAMID DERIVATIVES WITH INHIBITORY ACTIVITY AGAINST HISTONE DEACETYLASE AND METHOD FOR THE PREPARATION THEREOF<br/>[FR] DERIVES D'ARYLAMINOMETHYL-PROPENYL-BENZHYDROXYAMIDE PRESENTANT UNE ACTIVITE INHIBITRICE CONTRE L'HISTONE DEACETYLASE, ET METHODE DE PREPARATION DESDITS DERIVES
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2006025683A1

  公开（公告）日：2006-03-09

  This invention discloses a novel arylaminomethyl propenyl benzhydroxyamide derivative of formula (I) useful for preventing or treating various diseases induced by histone deacetylase, a method for preparing same and a pharmaceutical composition comprising same.

  这项发明揭示了一种新颖的芳基氨甲基丙烯基苯基羟基酰胺衍生物，其化学式为(I)，用于预防或治疗由组蛋白去乙酰化酶诱导的各种疾病，以及制备该衍生物的方法和包含该衍生物的药物组合物。
• NaNO ₂ /K ₂ S ₂ O ₈ ‐mediated Selective Radical Nitration/Nitrosation of Indoles: Efficient Approach to 3‐Nitro‐ and 3‐Nitrosoindoles
  作者：Adedamola Shoberu、Cheng‐Kun Li、Ze‐Kun Tao、Guo‐Yu Zhang、Jian‐Ping Zou

  DOI：10.1002/adsc.201900070

  日期：2019.5.14

  JPZ acknowledges financial support from the National Natural Science Foundation of China (No. 21172163, 21472133), the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and Key Laboratory of Organic Synthesis of Jiangsu Province (KJS1749).

  JPZ感谢国家自然科学基金（No. 21172163，21472133），江苏省高等学校优先学术计划（PAPD）和江苏省有机合成重点实验室（KJS1749）的资助。
• A Chlorinating Reagent: N-chloro-N-methoxybenzene Sulfonamide
  作者：Xiaoqiu Pu、Qingwei Li、Zehai Lu、Xianjin Yang

  DOI：10.1002/ejoc.201601226

  日期：2016.11

  Abstract: A structurally simple and reactive chlorinating reagent,N-chloro-N-methoxybenzenesulfonamide, was conveniently and economically prepared in high yield. 1,3-Diketones, β-keto esters, benzoyl trifluoroacetones, phenols, anisoles, heteroarenes andaromatic amines were chlorinated with it, obtaining chlorinated products in good to high yields.

  摘要: 一种结构简单、反应灵敏的氯化试剂N-氯-N-甲氧基苯磺酰胺可以方便、经济、收率高的制备。用它氯化1,3-二酮、β-酮酯、苯甲酰三氟丙酮、苯酚、苯甲醚、杂芳烃和芳香胺，得到氯化产物，收率高。
• [EN] AZA-OXO-INDOLES FOR THE TREATMENT AND PROPHYLAXIS OF RESPIRATORY SYNCYTIAL VIRUS INFECTION<br/>[FR] AZA-OXO-INDOLES POUR LE TRAITEMENT ET LA PROPHYLAXIE DE L'INFECTION À VIRUS RESPIRATOIRE SYNCYTIAL
  申请人：HOFFMANN LA ROCHE

  公开号：WO2014184163A1

  公开（公告）日：2014-11-20

  The invention provides compounds having the general formula: wherein R1, R2, R3, R4, R5, R6, W1, W2, W3, A and X are as described herein, compositions including the compounds and methods of using the compounds.

  这项发明提供了具有以下一般式的化合物：其中R1、R2、R3、R4、R5、R6、W1、W2、W3、A和X如本文所述，包括这些化合物的组合物以及使用这些化合物的方法。
• Iodine-mediated one-pot synthesis of indoles and 3-dimethylaminoindoles via annulation of enaminones
  作者：Alberto V. Jerezano、Ehecatl M. Labarrios、Fabiola E. Jiménez、María del Carmen Cruz、Diana C. Pazos、Rsuini U. Gutiérrez、Francisco Delgado、Joaquín Tamariz

  DOI：10.3998/ark.5550190.p008.138

  日期：——

  The synthesis of 2-carbonylindoles was achieved via a iodine-mediated cyclization of the corresponding enaminone precursors, which were form ed by reaction of the α-arylaminomethylene carbonyl derivatives with N,N′-dimethylformamide dimethyl acetal (DMFDMA). An alternative and more efficient procedure consisted of a similar cyclization of the enaminones, but under solvent-free and grinding reaction

  2-羰基吲哚的合成是通过相应烯胺酮前体的碘介导环化来实现的，该前体是通过α-芳基氨基亚甲基羰基衍生物与N,N'-二甲基甲酰胺二甲基乙缩醛（DMFDMA）反应形成的。另一种更有效的方法包括烯胺酮的类似环化，但在无溶剂和研磨反应条件下。在另一个碘促进的过程中，通过 α-芳基氨基亚甲基羰基衍生物和 DMFDMA 之间的一锅级联反应合成了 2-羰基-3-二甲基氨基吲哚。