6-溴吲哚-2-甲醛 | 105191-12-6

• 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: 6-溴吲哚-2-甲醛
• 中文别名: 6-溴-1H-吲哚-2-羧醛
• 英文名称: 6-bromo-1H-indole-2-carbaldehyde
• CAS: 105191-12-6
• 化学式: C₉H₆BrNO
• mdl: MFCD06738308
• 分子量: 224.057
• InChiKey: IGZHNWFLHSANSN-UHFFFAOYSA-N

物化性质

• 熔点：
  181-183°
• 沸点：
  395.6±22.0 °C(Predicted)
• 密度：
  1.727±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C，惰性气体

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-1h-indole-2-carbaldehyde
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H319: Causes serious eye irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 6-Bromo-1h-indole-2-carbaldehyde
CAS number: 105191-12-6

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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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H6BrNO
Molecular weight: 224.1

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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：

  6-溴吲哚-2-甲醛 在 哌啶 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium carbonate 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 23.5h， 生成 3,5-diethyl 4-[6-(5-methoxythiophen-2-yl)-1H-indol-2-yl]-2,6-bis(propan-2-yl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  一种吲哚类衍生物及其在糖尿病中的应用

  摘要：

  本发明公开了一种如式Ⅰ所示的吲哚类衍生物或其药学上可接受的盐其中，R1、R2、R3各自独立的选自H或OCH3。体外DPP‑4酶抑制试验中所列化合物对DPP‑4的IC50值均小于omarigliptin和Sitagliptin。表明本发明化合物具有较好的DPP‑4抑制活性，可以作为治疗和/或预防非胰岛素依赖性糖尿病、高血糖或胰岛素抗性的药物进行更加深层次的研究。

  公开号：

  CN108503632B
• 作为产物：
  描述：

  6-溴吲哚-2-羧酸乙酯 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.17h， 生成 6-溴吲哚-2-甲醛
  参考文献：
  名称：

  杂芳烃向酮的碳催化的对映选择性芳族N-亲核加成反应。

  摘要：

  杂芳基醛的芳族氮原子被卡宾催化剂活化以与酮亲电子试剂反应。以良好至优异的产率和光学纯度提供多功能的环状N，O-乙缩醛产物。我们的反应涉及空前的氮杂富烯型酰基唑鎓中间体的形成。各种各样的N-杂芳族醛和缺电子的酮底物可以有效地实现这种转化。通过该协议提供的几种手性N，O-乙缩醛产品表现出优异的抗青枯菌（Rsstonia solanacearum）的抗菌活性，在开发用于植物保护的新型农业化学品中具有重要的价值。

  DOI：

  10.1002/anie.201912160

文献信息

• [EN] BICYCLIC INHIBITORS OF PAD4<br/>[FR] INHIBITEURS BICYCLIQUES DE PAD4
  申请人：PADLOCK THERAPEUTICS INC

  公开号：WO2017100594A1

  公开（公告）日：2017-06-15

  The present invention provides compounds useful as inhibitors of PAD4, compositions thereof, and methods of treating PAD4-related disorders.

  本发明提供了用作PAD4抑制剂的化合物、其组合物以及治疗与PAD4相关疾病的方法。
• [EN] THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION<br/>[FR] COMPOSÉS THÉRAPEUTIQUES ET MÉTHODES POUR TRAITER UNE INFECTION
  申请人：UNIV RUTGERS

  公开号：WO2019099402A1

  公开（公告）日：2019-05-23

  Disclosed herein are compounds of formula (I), or a salt thereof and compositions comprising compounds of formula I that exhibit antibacterial activities, when tested alone and/or in combination with a bacterial efflux pump inhibitor. Also disclosed are methods of treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I alone or in combination with the administration of a bacterial efflux pump inhibitor.

  本文披露了化合物的结构式（I）或其盐，以及包含表现出抗菌活性的化合物的组合物的组合物，当单独测试和/或与细菌外排泵抑制剂结合时。还披露了治疗或预防动物细菌感染的方法，包括向动物单独或与细菌外排泵抑制剂的给药结合给动物的结构式（I）的化合物。
• [EN] ANTIBIOTIC COMPOUNDS, PHARMACEUTICAL FORMULATIONS THEREOF AND METHODS AND USES THEREFOR<br/>[FR] COMPOSÉS ANTIBIOTIQUES, LEURS FORMULATIONS PHARMACEUTIQUES, AINSI QUE PROCÉDÉS ASSOCIÉS ET UTILISATIONS ASSOCIÉES
  申请人：UNIV FRASER SIMON

  公开号：WO2017075694A1

  公开（公告）日：2017-05-11

  The present invention relates to compounds of formula (I) wherein G1 to G8 are as defined herein. The compounds are PK inhibitors and as such represent a new approach to treating pathogenic infections, including multidrug resistant pathogens. Disclosed herein are the compounds of formula (I), pharmaceutical compositions comprising the compounds of formula (I) and their use in the treatment of antimicrobial infection. (Formula (1))

  本发明涉及式(I)的化合物，其中G1至G8如本文所定义。这些化合物是PK抑制剂，因此代表了治疗病原体感染的新方法，包括多药耐药病原体。本文披露了式(I)的化合物，包括含有式(I)的药物组合物以及它们在抗微生物感染治疗中的应用。
• [EN] MACROCYCLIC INHIBITORS OF PEPTIDYLARGININE DEIMINASES<br/>[FR] INHIBITEURS MACROCYCLIQUES DE PEPTIDYLARGININE DÉIMINASES
  申请人：GILEAD SCIENCES INC

  公开号：WO2021222353A1

  公开（公告）日：2021-11-04

  The present disclosure relates to novel compounds for use in therapeutic treatement of a disease associated with peptidylarginine deiminases (PADs), such as peptidylarginine deiminase type 4 (PAD4). The present disclosure also relates to processes and intermediates for the preparation of such compounds, methods of using such compounds and pharmaceutical compositions comprising the compounds described herein.

  本公开涉及用于治疗与肽精氨酸脱亚氨酶（PADs）相关的疾病的新化合物，例如肽精氨酸脱亚氨酶类型4（PAD4）。本公开还涉及用于制备这些化合物的过程和中间体，使用这些化合物的方法以及包含所述化合物的药物组合物。
• Synthesis of Indole‐ and Pyrrole‐Fused Seven‐Membered Nitrogen Heterocycles via Acid‐Base Switchable Cyclization Involving Cleavage of Amide C−N Bonds
  作者：Yanke Hao、Pan Zhou、Kaikai Niu、Hongjian Song、Yuxiu Liu、Jingjing Zhang、Qingmin Wang

  DOI：10.1002/adsc.202101126

  日期：2022.1.18

  We report the method for synthesis of indole- and pyrrole-fused seven-membered nitrogen heterocycles by means of acid-base switchable cyclization reactions. The reactions involved cleavage of amide C−N bonds, chemoselective N-1 or C-3 acylation, and 1,4-Michael addition. This method could be used to construct two different kinds of seven-membered rings in one step from the same starting material without

  我们报告了通过酸碱可切换环化反应合成吲哚和吡咯稠合的七元氮杂环的方法。该反应涉及酰胺 C-N 键的断裂、化学选择性 N-1 或 C-3 酰化以及 1,4-Michael 加成。该方法可用于从相同的起始材料一步构建两种不同类型的七元环，而无需过渡金属催化剂。