3-溴喹啉-1-氧化物 | 22615-00-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 3-溴喹啉-1-氧化物
• 英文名称: 3-bromoquinoline N-oxide
• 英文别名: 3-bromoquinoline 1-oxide；3-bromo-1-oxidoquinolin-1-ium
• CAS: 22615-00-5
• 化学式: C₉H₆BrNO
• 分子量: 224.057
• InChiKey: LANTXZGXVINCPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromoquinoline-1-oxide
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: 3-Bromoquinoline-1-oxide
CAS number: 22615-00-5

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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: 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  3-溴喹啉	3-bromoquinoline	5332-24-1	C9H6BrN	208.057

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3-溴喹啉	3-bromoquinoline	5332-24-1	C9H6BrN	208.057
  2,3-二溴喹啉	2,3-dibromoquinoline	13721-00-1	C9H5Br2N	286.953
  3-溴-2-碘喹啉	3-bromo-2-iodoquinoline	898559-23-4	C9H5BrIN	333.954
  ——	3-bromo-2(1H)-quinolinethione	629617-25-0	C9H6BrNS	240.123
  3-溴喹啉-2(1氢)-酮	3-bromoquinolin-2-one	939-16-2	C9H6BrNO	224.057
  3-溴-2-氯喹啉	3-bromo-2-chloroquinoline	101870-60-4	C9H5BrClN	242.502
  3-溴-5-硝基喹啉-1-氧化物	3-bromo-5-nitro-quinoline-1-oxide	860195-55-7	C9H5BrN2O3	269.054
  ——	3-hydroxyquinoline-1-oxide	59953-98-9	C9H7NO2	161.16
  2-氰基-3-溴喹啉	3-bromoquinoline-2-carbonitrile	61830-11-3	C10H5BrN2	233.067

反应信息

• 作为反应物：
  描述：

  3-溴喹啉-1-氧化物 在 硫酸 、 potassium nitrate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以46%的产率得到3-溴-4-硝基喹啉-1-氧化物
  参考文献：
  名称：

  CGRP ANTAGONISTS

  摘要：

  本发明涉及一般式I的新的CGRP拮抗剂，其中U、V、X、Y、R1、R2和R3如下所述定义，其互变异构体、同分异构体、对映异构体、水合物、混合物及其盐和盐的水合物，特别是其与无机或有机酸或碱的生理上可接受的盐，含有这些化合物的药物组合物，其用途以及制备它们的过程。

  公开号：

  US20110059954A1
• 作为产物：
  描述：

  3-bromo-1-hydroxyquinolin-4-imine 在 硫酸 、 sodium nitrite 作用下， 生成 3-溴喹啉-1-氧化物
  参考文献：
  名称：

  Naito, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1947, vol. 67, p. 246

  摘要：

  DOI：

文献信息

• [EN] CRBN LIGANDS AND USES THEREOF<br/>[FR] LIGANDS CRBN ET LEURS UTILISATIONS
  申请人：KYMERA THERAPEUTICS INC

  公开号：WO2019140387A1

  公开（公告）日：2019-07-18

  The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物抑制CRBN并治疗CRBN介导的疾病的方法。
• Co(III)-Catalyzed C–H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions
  作者：Ankit Kumar Dhiman、Ankita Thakur、Inder Kumar、Rakesh Kumar、Upendra Sharma

  DOI：10.1021/acs.joc.0c01237

  日期：2020.7.17

  A cobalt(III)-catalyzed C-8 selective C–H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines

  公开了在温和条件下使用重氮唑啉作为酰胺化试剂的钴（III）催化的喹啉N-氧化物的C-8选择性C–H酰胺化。该反应以优异的官能团相容性有效地进行。通过克规模合成C-8酰胺喹啉N-氧化物并将该酰胺化产物转化为官能化喹啉，证明了本方法的实用性。此外，开发的催化方法也适用于N-嘧啶二氢吲哚的C-7酰胺化和苯甲酰胺的正酰胺化。
• From Pyridine-<i>N</i>-oxides to 2-Functionalized Pyridines through Pyridyl Phosphonium Salts: An Umpolung Strategy
  作者：Dmitry I. Bugaenko、Marina A. Yurovskaya、Alexander V. Karchava

  DOI：10.1021/acs.orglett.1c02165

  日期：2021.8.6

  The reactions of pyridine-N-oxides with Ph3P under the developed conditions provide an unprecedented route to (pyridine-2-yl)phosphonium salts. Upon activation with DABCO, these salts readily serve as functionalized 2-pyridyl nucleophile equivalents. This umpolung strategy allows for the selective C2 functionalization of the pyridine ring with electrophiles, avoiding the generation and use of unstable

  吡啶-N-氧化物与Ph 3 P 在已开发条件下的反应为（吡啶-2-基）鏻盐提供了前所未有的途径。用 DABCO 活化后，这些盐很容易用作功能化的 2-吡啶基亲核试剂等价物。这种 umpolung 策略允许使用亲电试剂对吡啶环进行选择性 C2 官能化，避免产生和使用不稳定的有机金属试剂。该协议在环境温度下运行并耐受敏感的官能团，从而能够合成其他具有挑战性的化合物。
• Cu-Catalyzed carbamoylation<i>versus</i>amination of quinoline<i>N</i>-oxide with formamides
  作者：Yan Zhang、Shiwei Zhang、Guangxing Xu、Min Li、Chunlei Tang、Weizheng Fan

  DOI：10.1039/c8ob02844c

  日期：——

  An efficient, direct carbamoylation and amination of quinoline N-oxides with formamides to access 2-carbamoyl and 2-amino quinolines has been developed through copper-catalyzed C–C and C–N bond formations via cross-dehydrogenative coupling reactions. The reaction proceeds smoothly over a broad range of substrates with excellent functional group tolerance under mild conditions. Mechanistic studies suggest

  通过铜催化的C-C和C-N键的形成，通过交叉脱氢偶联反应，已开发出一种高效，直接的氨基甲酰基化和喹啉N-氧化物与甲酰胺的胺化反应，以生成2-氨基甲酰基和2-氨基喹啉。在温和条件下，该反应可在广泛的具有良好官能团耐受性的底物上顺利进行。机理研究表明，根据甲酰胺N原子上不同的取代基，在TBHP存在下，该反应是由甲酰胺基或脱羰基氨酰基自由基的形成引发的。
• Visible-Light Photocatalyzed Deoxygenation of N-Heterocyclic <i>N</i>-Oxides
  作者：Kyu Dong Kim、Jun Hee Lee

  DOI：10.1021/acs.orglett.8b03446

  日期：2018.12.7

  operationally simple method is described that allows for the chemoselective deoxygenation of a wide range of N-heterocyclic N-oxides (a total of 36 examples). This visible-light-induced protocol features the use of only commercially available reagents, room-temperature conditions, and unprecedented chemoselective removal of the oxygen atom in a quinoline N-oxide in the presence of a pyridine N-oxide in the

  描述了一种可扩展且操作简单的方法，该方法允许对各种N-杂环N-氧化物进行化学选择脱氧（总共36个实例）。该可见光诱导方案的特点是仅使用市售试剂，室温条件下以及在相同分子中存在吡啶N-氧化物存在的情况下，通过喹啉N-氧化物空前的化学选择性除去喹啉N-氧化物中的氧原子。明智地选择光催化剂。

表征谱图