6-溴-5-硝基喹啉 | 98203-04-4

• 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: 6-溴-5-硝基喹啉
• 英文名称: 6-bromo-5-nitroquinoline
• 英文别名: 6-bromo-5-nitro-quinoline；6-Brom-5-nitro-chinolin
• CAS: 98203-04-4
• 化学式: C₉H₅BrN₂O₂
• 分子量: 253.055
• InChiKey: ISBMTVQQECNRQY-UHFFFAOYSA-N

物化性质

• 熔点：
  130°C
• 密度：
  1.7693 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 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：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 6-Bromo-5-nitroquinoline
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-Bromo-5-nitroquinoline
CAS number: 98203-04-4

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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: C9H5BrN2O2
Molecular weight: 253.1

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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-5-硝基喹啉 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以31%的产率得到6-bromo-5-nitroquinoline-N-oxide
  参考文献：
  名称：

  Bashir, Mohammad; Kingston, David G. I.; Carman, Robert J., Heterocycles, 1987, vol. 26, # 11, p. 2877 - 2886

  摘要：

  DOI：
• 作为产物：
  描述：

  6-溴喹啉 在 硫酸 、 potassium nitrate 作用下， 以94%的产率得到6-溴-5-硝基喹啉
  参考文献：
  名称：

  一种用于设计强效、高选择性和脑渗透性 N-肉豆蔻酰基转移酶抑制剂的分子杂交方法。

  摘要：

  晶体学已经指导了两个系列的布氏锥虫 N-肉豆蔻酰转移酶 (NMT) 抑制剂的杂交，从而产生了一个新的高选择性系列。结合来自两种药效团的选择性增强元素的效果被证明是相加的，并导致化合物对 TbNMT 与 HsNMT 的选择性超过 1000 倍。混合系列的进一步优化已经确定了具有显着杀锥虫活性的化合物，能够穿过血脑屏障。通过使用 CF-1 mdr1a 缺陷小鼠，我们能够在 2 期非洲昏睡病小鼠模型中证明体内完全治愈。这项工作和以前的工作为 NMT 作为人类非洲锥虫病在外周和中枢神经系统疾病阶段的药物靶点提供了非常有力的验证。

  DOI：

  10.1021/acs.jmedchem.8b00884

文献信息

• A Mild and General Larock Indolization Protocol for the Preparation of Unnatural Tryptophans
  作者：Kangway V. Chuang、Madeleine E. Kieffer、Sarah E. Reisman

  DOI：10.1021/acs.orglett.6b02477

  日期：2016.9.16

  A mild and general protocol for the Pd(0)-catalyzed heteroannulation of o-bromoanilines and alkynes is described. Application of a Pd(0)/P(tBu)3 catalyst system enables the efficient coupling of o-bromoanilines at 60 °C, mitigating deleterious side reactions and enabling access to a broad range of useful unnatural tryptophans. The utility of this new protocol is demonstrated in the highly convergent

  描述了一种温和而通用的协议，用于Pd（0）催化邻溴代苯胺和炔烃的杂环化反应。Pd（0）/ P（t Bu）3催化剂体系的应用使邻溴代苯胺在60°C时能有效偶联，从而减轻了有害的副反应并能接触到各种有用的非天然色氨酸。该新方案的效用在双吲哚天然产物（-）-aspergilazine A的高度收敛的全合成中得到了证明。
• Activation of 6-bromoquinoline by nitration: synthesis of morpholinyl and piperazinyl quinolines
  作者：Osman Çakmak、Salih Ökten、Dilek Alımlı、Aisha Saddiqa、Cem Cüneyt Ersanlı

  DOI：10.24820/ark.5550190.p010.374

  日期：——

  quinoline, very few general synthetic routes are described in the literature starting from quinoline or tetrahydroquinoline. A simple and convenient method for the polyfunctionalization of quinolines via nitration of bromoquinolines has been developed. This method represents a new synthetic approach to convert brominated nitroquinoline derivatives into useful cyclic amines via nucleophilic-substitution

  喹啉是许多重要天然产物和药理活性化合物的关键骨骼成分。尽管对喹啉的衍生化进行了大量研究，但文献中很少描述从喹啉或四氢喹啉开始的一般合成路线。已经开发了一种通过溴喹啉硝化使喹啉多官能化的简单方便的方法。该方法代表了一种新的合成方法，通过亲核取代 (SNAr) 反应将溴化硝基喹啉衍生物转化为有用的环胺。
• BICYCLIC TRIAZOLES AS PROTEIN KINASE MODULATORS
  申请人：Bounaud Pierre-Yves

  公开号：US20090258855A1

  公开（公告）日：2009-10-15

  The present disclosure provides bicyclic triazole protein kinase modulators and methods of using these compounds to treat diseases mediated by kinase activity.

  本公开提供了双环三唑蛋白激酶调节剂以及使用这些化合物治疗由激酶活性介导的疾病的方法。
• Bicyclic triazoles as protein kinase modulators
  申请人：Bounaud Pierre-Yves

  公开号：US08507489B2

  公开（公告）日：2013-08-13

  The present disclosure provides bicyclic triazole protein kinase modulators and methods of using these compounds to treat diseases mediated by kinase activity.

  本公开提供了双环三唑蛋白激酶调节剂，并提供使用这些化合物治疗由激酶活性介导的疾病的方法。
• [EN] DEGRADER COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE DÉGRADATION ET LEURS UTILISATIONS
  申请人：CALICO LIFE SCIENCES LLC

  公开号：WO2022271727A1

  公开（公告）日：2022-12-29

  Provided herein are compounds, compositions, and methods useful for degrading protein tyrosine phosphatase, e.g., protein tyrosine phosphatase non-receptor type 2 (PTPN2) and/or protein tyrosine phosphatase non-receptor type 1 (PTPN1), and for treating related diseases favorably responsive to PTPN1 or PTPN2 inhibitor treatment, e.g., a cancer or a metabolic disease.

  本文提供了用于降解蛋白酪氨酸磷酸酶（如蛋白酪氨酸磷酸酶非受体2型（PTPN2）和/或蛋白酪氨酸磷酸酶非受体1型（PTPN1））的化合物、组合物和方法，以及用于治疗对PTPN1或PTPN2抑制剂治疗有良好反应的相关疾病（如癌症或代谢性疾病）的化合物、组合物和方法。