6-氯-1-甲基-1H-吲哚 | 155868-51-2

• 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: 6-氯-1-甲基-1H-吲哚
• 英文名称: 6-chloro-1-methyl-1H-indole
• 英文别名: 6-chloro-1-methylindole；N-methyl-6-chloroindole；1-methyl-6-chloroindole；6-chloro-N-methylindole
• CAS: 155868-51-2
• 化学式: C₉H₈ClN
• 分子量: 165.622
• InChiKey: YDLOPHRVGMIZDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

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
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Chloro-1-methyl-1H-indole
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: 6-Chloro-1-methyl-1H-indole
CAS number: 155868-51-2

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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: C9H8ClN
Molecular weight: 165.6

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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：

  6-氯-1-甲基-1H-吲哚 在 potassium tert-butylate 、 N,N-二甲基甲酰胺 作用下， 反应 24.0h， 以63%的产率得到1-甲基吲哚
  参考文献：
  名称：

  可见光诱导的碱促进的芳基氟化物，氯化物，溴化物和碘化物的无过渡金属脱卤化作用

  摘要：

  我们报告了简单有效的芳基卤化物的可见光诱导的无过渡金属氢化。可见光和碱的组合系统用于引发所需的自由基介导的氢化反应。在温和条件下，可以将多种芳基氟化物，氯化物，溴化物和碘化物还原成相应的（杂）芳烃。可以容忍各种官能团和其他杂环化合物。

  DOI：

  10.1021/acs.orglett.0c00827
• 作为产物：
  描述：

  6-chloro-1-methylindoline 在 4-二甲氨基吡啶 、 ethyl 2-(4-nitrophenyl)hydrazinecarboxylate 、 氧气 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 以72 %的产率得到6-氯-1-甲基-1H-吲哚
  参考文献：
  名称：

  偶氮/酰肼氧化还原铜催化叔吲哚有氧氧化脱氢生成吲哚

  摘要：

  偶氮化合物用途广泛，用途广泛。它们是光延反应和脱氢反应中的关键试剂。然而，偶氮化合物或其相应的酰肼从未在叔胺催化脱氢中进行过研究。在此，我们报道了一种使用 CuCl、4-(二甲基氨基)吡啶 (DMAP) 和 2-(4-硝基苯基)肼-1-羧酸酯的共催化系统，用于将叔吲哚啉有氧氧化脱氢为其相应的吲哚。

  DOI：

  10.1039/d3nj05172b

文献信息

• Rh(II)-catalyzed Denitrogenative Cascade of 1,2,3-Triazolyl Propiolates and Indoles: Access to Butenolide Tethered Homotryptamines
  作者：Kuntal Pal、Chandra M. R. Volla

  DOI：10.1021/acs.orglett.1c01215

  日期：2021.6.4

  This methodology provides facile access to butenolide tethered homotryptamines in good to excellent yields under operationally simple conditions and features a broad substrate scope. Overall, the reaction sequence involves the formation of three new bonds (two C–C and one C–O) in a nucleophilic cascade manner. Additionally, an intramolecular rearrangement of these derivatives to thermodynamically more

  已开发出一种高效的 Rh(II) 催化吲哚与 1,2,3-三唑基丙炔酸酯的脱氮反应。这种方法可以在操作简单的条件下轻松获得丁烯内酯系留的同色胺，并具有广泛的底物范围。总的来说，反应序列涉及以亲核级联方式形成三个新键（两个 C-C 和一个 C-O）。此外，还证明了这些衍生物的分子内重排为热力学更稳定的丁烯内酯。
• Sequential 1,3-<i>N</i>- to <i>C</i>- and 1,3-<i>C</i>- to <i>C</i>-Migration of Sulfonyl Groups through the Synthesis of 1,4-Diazepines from the Aza-[5 + 2] Cycloaddition of Indoloazomethine Ylides
  作者：Namrim Heo、Ilyong Jung、Dae Kyum Kim、Sang Hoon Han、Kooyeon Lee、Phil Ho Lee

  DOI：10.1021/acs.orglett.0c02333

  日期：2020.8.21

  sequential 1,3-N- to C- and 1,3-C- to C-migration of sulfonyl groups through the synthesis of 1,4-diazepines from an operationally simple thermal aza-[5 + 2] cycloaddition reaction of indoloazomethine ylides with dialkyl acetylenedicarboxylates under mild conditions, leading to the formation of C-sulfonylated 1,4-diazepines.

  本文描述了通过从操作简单的热氮杂-[5 + 2]环加成反应合成1,4-二氮杂s，磺酰基依次从1,3- N-到C-和1,3- C-到C-迁移。吲哚并甲亚胺基化物在温和条件下与乙炔二羧酸二烷基酯反应，导致形成C-磺酰化的1，4-二氮杂pine。
• Rh(II)‐Catalyzed Denitrogenative Reaction of 1,2,3‐Triazolyl Esters with Indoles or Arenes: Efficient Synthesis of Homotryptamines or Allylamines
  作者：Kuntal Pal、Geetanjali S. Sontakke、Chandra M. R. Volla

  DOI：10.1002/adsc.202000632

  日期：2020.9.8

  efficient strategy for the synthesis of structurally diverse homotryptamines and allyl amines via a Rh(II)‐catalyzed tandem reaction of 1,2,3‐triazolyl esters with either indoles or 1,3,5‐trimethoxybenzene has been developed. The reaction proceeds via Rh(II)‐catalyzed intramolecular rearrangement of triazoles into 1‐azadienes followed by regioselective nucleophilic addition. The efficiency of the current

  通过1,2,3-三唑基酯与吲哚或1,3,5-三甲氧基苯的Rh（II）催化串联反应，已开发出一种有效的策略来合成结构多样的高色胺和烯丙基胺。该反应通过Rh（II）催化的三唑分子内重排反应成1-氮杂二烯，然后进行区域选择性亲核加成反应。当前方案的效率通过广泛的底物范围，克规模的合成以及高色胺到其他生物学相关杂环的进一步官能化得到说明。
• Visible-Light-Promoted Redox Neutral C–H Amidation of Heteroarenes with Hydroxylamine Derivatives
  作者：Qixue Qin、Shouyun Yu

  DOI：10.1021/ol501457s

  日期：2014.7.3

  redox neutral direct C–H amidation of heteroarenes has been achieved. Hydroxylamine derivatives, which are easily accessed, have been employed as tunable nitrogen sources. These reactions were enabled by a visible-light-promoted single-electron transfer pathway without a directing group. A variety of heteroarenes, such as indoles, pyrroles, and furans, could go through this amidation with high yields (up

  在室温下实现了杂芳烃的氧化还原中性直接C–H酰胺化。容易获得的羟胺衍生物已被用作可调氮源。这些反应是通过可见光促进的单电子转移途径实现的，而没有指导基团。各种杂芳烃，例如吲哚，吡咯和呋喃，都可以高产率（高达98％）通过酰胺化反应。这些反应具有高度的区域选择性，所有产物均作为单一的区域异构体被分离出来。
• Metal‐Free Three‐Component Selenopheno[2,3‐ <i>b</i> ]indole Formation through Double C−H Selenylation with Selenium Powder
  作者：Penghui Ni、Jing Tan、Wenqi Zhao、Huawen Huang、Guo‐Jun Deng

  DOI：10.1002/adsc.201901023

  日期：2019.12.3

  A facile metal‐free entry to novel selenopheno[2,3‐b]indole motif is described. The three‐component assembly of indoles, aromatic ketones, and selenium powder is enabled by the IBr‐promoted highly selective double C–H selenylation/annulation. This protocol provides a novel access to a diverse variety of selenopheno[2,3‐b]indoles with good efficacy and broad functional group compatibility.

  描述了一种新颖的硒代苯并[2,3- b ]吲哚基序的无金属入口。吲哚，芳族酮和硒粉的三组分组装是由IBr促进的高选择性双C–H硒化/环化反应实现的。该协议提供了一种新颖的途径来获得具有良好疗效和广泛的官能团相容性的硒硒酚[2,3- b ]吲哚。