4-溴-(9ci)-1H-吲哚-3-乙酸 | 89245-41-0

• 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: 4-溴-(9ci)-1H-吲哚-3-乙酸
• 中文别名: 4-溴吲哚-3-乙酸；4-溴-1H-吲哚-3-乙酸；4-溴-3-吲哚乙酸
• 英文名称: 4-bromo-3-indoleacetic acid
• 英文别名: 4-bromoindole-3-acetic acid；2-(4-Bromo-1H-indol-3-yl)acetic acid
• CAS: 89245-41-0
• 化学式: C₁₀H₈BrNO₂
• mdl: MFCD09751717
• 分子量: 254.083
• InChiKey: AQIDQZFQDRENOY-UHFFFAOYSA-N

物化性质

• 熔点：
  185-187℃ (DEC.)
• 沸点：
  466.0±30.0 °C(Predicted)
• 密度：
  1.746

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  53.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(4-Bromo-1H-indol-3-yl)acetic acid
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-(4-Bromo-1H-indol-3-yl)acetic acid
CAS number: 89245-41-0

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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: C10H8BrNO2
Molecular weight: 254.1

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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, hydrogen bromide.

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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：

  4-溴-(9ci)-1H-吲哚-3-乙酸 在 lithium aluminium tetrahydride 、 2-碘酰基苯甲酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 4-bromoindole-3-acetaldehyde
  参考文献：
  名称：

  通过Bi（OTf）3-催化的串联Friedel-Crafts烷基化/ Thia-Michael加成反应快速地一锅获得独特的3,4-二氢硫代吡喃并[3,4-b]吲哚-1（9H）-亚胺

  摘要：

  已经开发了一种有趣的新途径，可通过串联的Friedel-Crafts烷基化反应和Thia-Michael加成反应获得3,4-二氢硫代吡喃并[3,4- b ]吲哚-1（9 H）-亚胺。此外，所描述的方法学也适用于研究较少的四氢-1 H - thiepino [3,4- b ]吲哚支架。该策略以原子经济，各种官能团耐受性和广泛的底物范围为关键特征。

  DOI：

  10.1002/ejoc.201801012
• 作为产物：
  描述：

  4-硝基芦竹碱 在 sodium hydroxide 、 titanium(III) chloride 、 氢溴酸 、 sodium hydride 、 copper(I) bromide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 14.5h， 生成 4-溴-(9ci)-1H-吲哚-3-乙酸
  参考文献：
  名称：

  The chemistry of indoles. XXIV. Syntheses of 3-indoleacetic acid and 3-indoleacetonitrile having a halogeno group and a carbon functional group at the 4-position.

  摘要：

  首次合成了多种4-卤代-3-吲哚乙酸和-3-吲哚乙腈，采用了桑德梅耶反应或施密特反应，展示了4-吲哚二氮盐在4-取代吲哚化学中的多样性。通过区域选择性的铊化-卤化开发了一种实用的4-卤代吲哚合成方法，所生成的产品也可转化为4-卤代-3-吲哚乙酸。此外，还报道了4-甲酰基-3-吲哚乙腈的首次合成。

  DOI：

  10.1248/cpb.33.3696

文献信息

• 一种取代吲哚-3-乙酸的合成方法
  申请人：东南大学

  公开号：CN104311469B

  公开（公告）日：2016-10-26

  本发明提供的一种取代吲哚‑3‑乙酸的合成方法，包括以下步骤：(1)以取代吲哚为起始原料，与酰基化试剂在催化剂作用下经过傅‑克酰基化得到1,3‑二乙酰基取代吲哚；(2)中间体1,3‑二乙酰基取代吲哚无需精制，直接与吗啉和硫磺经Willgerodt‑Kindler重排反应，在无机碱催化下水解，酸化后得到取代吲哚‑3‑乙酸。
• Copper-Mediated Decarboxylative Coupling between Arylacetic Acids and 1,3-Dicarbonyl Compounds
  作者：Yinrong Wu、Kangmei Wen、Jiewen Chen、Jie Shi、Xingang Yao、Xiaodong Tang

  DOI：10.1021/acs.orglett.1c02897

  日期：2021.10.15

  A copper-mediated decarboxylative coupling reaction between arylacetic acids and 1,3-dicarbonyl compounds was described. Significantly, methanocycloocta[b]indoles were also obtained by sequential intramolecular dehydrocyclization process in some cases. This protocol featured a broad substrate scope, simple operations, and good yields. Moreover, the products exhibited potent antiproliferative activity

  描述了芳基乙酸和 1,3-二羰基化合物之间铜介导的脱羧偶联反应。值得注意的是，在某些情况下，还可以通过顺序分子内脱氢环化过程获得甲氧基环八[ b ]吲哚。该协议具有广泛的基板范围、简单的操作和良好的产量。此外，通过 MTT 测定，这些产品对人类癌细胞系表现出有效的抗增殖活性。
• Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst
  作者：Hiromichi Egami、Ryo Hotta、Minami Otsubo、Taiki Rouno、Tomoki Niwa、Kenji Yamashita、Yoshitaka Hamashima

  DOI：10.1021/acs.orglett.0c02026

  日期：2020.7.17

  Asymmetric dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeds under mild reaction conditions to provide fluoropyrroloindoline derivatives in a highly enantioselective manner. Various substitution patterns on the indole ring are well tolerated. To facilitate the reaction and ensure reproducibility, the addition

  使用二羧酸酯相转移催化剂研究了吲哚衍生物的不对称脱芳烃氟环化反应。该反应在温和的反应条件下进行，以高度对映选择性的方式提供氟吡咯并吲哚啉衍生物。吲哚环上的各种取代方式都具有良好的耐受性。为了促进反应并确保可重复性，必须添加水，并讨论其可能的作用。
• Copper-Catalyzed C-3 Functionalization of Imidazo[1,2-<i>a</i>]pyridines with 3-Indoleacetic Acids
  作者：Yinrong Wu、Lu Li、Kangmei Wen、Jie Deng、Jiewen Chen、Jie Shi、Ting Wu、Jianxin Pang、Xiaodong Tang

  DOI：10.1021/acs.joc.1c01371

  日期：2021.9.3

  A copper-catalyzed C-3 functionalization of imidazo[1,2-a]pyridines with 3-indoleacetic acids through an aerobic oxidative decarboxylative process has been developed. The protocol provided a series of 3-(1H-indol-3-ylmethyl)-imidazo[1,2-a]pyridines in moderate to good yields under simple reaction conditions. Importantly, some products exhibited potent antiproliferative activity in cancer cell lines

  通过有氧氧化脱羧过程，铜催化的咪唑并 [1,2- a ] 吡啶与 3-吲哚乙酸的C-3 官能化已被开发。该方案提供了一系列 3-(1 H -indol-3-ylmethyl)-imidazo[1,2- a ] 吡啶，在简单的反应条件下，产率中等至良好。重要的是，一些产品在癌细胞系中表现出有效的抗增殖活性。
• Parameterization of Acyclic Diaminocarbene Ligands Applied to a Gold(I)-Catalyzed Enantioselective Tandem Rearrangement/Cyclization
  作者：Zachary L. Niemeyer、Suresh Pindi、Dimitri A. Khrakovsky、Christian N. Kuzniewski、Cynthia M. Hong、Leo A. Joyce、Matthew S. Sigman、F. Dean Toste

  DOI：10.1021/jacs.7b08791

  日期：2017.9.20

  are developed in the context of a gold catalyzed enantioselective tandem [3,3]-sigmatropic rearrangement-[2+2]-cyclization. Surrogate structures enable the rapid identification of parameters that reveal mechanistic characteristics. The observed selectivity trends are validated in a robust multivariate analysis facilitating the development of a highly enantioselective process.

  在金催化的对映选择性串联 [3,3]-sigmatropic 重排-[2+2]-环化的背景下开发了无环二氨基卡宾配体的计算描述符。替代结构能够快速识别揭示机械特性的参数。观察到的选择性趋势在稳健的多变量分析中得到验证，促进了高度对映选择性过程的发展。