8-溴-5-三氟甲基喹啉 | 917251-92-4

• 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: 8-溴-5-三氟甲基喹啉
• 英文名称: 8-bromo-5-(trifluoromethyl)quinoline
• CAS: 917251-92-4
• 化学式: C₁₀H₅BrF₃N
• 分子量: 276.056
• InChiKey: SLRQZPDPELUOEM-UHFFFAOYSA-N

物化性质

• 沸点：
  309.6±37.0 °C(Predicted)
• 密度：
  1.658±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933499090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P264,P270,P280,P301+P310+P330,P305+P351+P338,P337+P313,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H319
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
8-Bromo-5-trifluoromethylquinoline
Product Name:
Synonyms: 8-Bromo-5-(trifluoromethyl)quinoline

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H319: Causes serious eye irritation
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
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: 8-Bromo-5-trifluoromethylquinoline
CAS number: 917251-92-4

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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: C10H5BrF3N
Molecular weight: 276.1

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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 fluoride, 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
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (8-Bromo-5-trifluoromethylquinoline)

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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：

  8-溴-5-三氟甲基喹啉 在 二苯甲酮亚胺 、 palladium diacetate 、 caesium carbonate 、 盐酸 作用下， 以 甲苯 、 四氢呋喃 、 乙醇 为溶剂， 以90 %的产率得到5-三氟甲基-8-喹啉胺
  参考文献：
  名称：

  用于改进 Ni(II) 介导的 C(sp3)–H 激活的电子导向基团修饰：8-氨基喹啉的 Hammett 研究

  摘要：

  与其他N、N-二齿导向基团相比，8-氨基喹啉 (AQ) 导向基团因在未活化的底物中促进优异的 C-H 键活化而受到相当多的关注。然而，对于镍来说，AQ 在 C-H 活化反应中的作用尚未完全认识到。C(sp 3 )–H 激活中5 取代 AQ 的动力学实验和哈米特分析揭示了富电子和贫电子取代 AQ 之间的不连续趋势，从而在 Ni(II) 介导的 C 中产生非线性哈米特图(sp 3 )–H 叔脲的活化。我们已经鉴定并合成了顺磁性tris -AQ 连接的阴离子 Ni(II) 物种，例如 Na[ fac -(1d – ) 3 Ni]（配合物5）。我们提出顺磁配合物参与与经历 C-H 激活的活性物质的预平衡。我们假设这些配位饱和的顺磁三脲酸盐配合物有利于吸电子导向基团，从而影响 C-H 活化的初始速率。这些观察结果还指出了催化剂形态的重要性和配体电子特性的作用，而不仅仅是导致形态变化和镍催化反应速率随后变化的空间特征。

  DOI：

  10.1021/acs.organomet.3c00199
• 作为产物：
  描述：

  2-溴-5-三氟甲苯苯胺 、 甘油 在 ferrous(II) sulfate heptahydrate 、 甲烷磺酸 、 sodium 3-nitrobenzenesulfonate 作用下， 反应 20.0h， 以27%的产率得到8-溴-5-三氟甲基喹啉
  参考文献：
  名称：

  双功能有机催化剂通过卤代反应诱导8-芳基喹啉中的轴向手性。

  摘要：

  轴向手性杂二芳基的对映选择性合成是通过3-（喹啉-8-基）苯酚的芳香亲电卤化与双功能有机催化剂来控制的，该双功能有机催化剂在连续的卤化过程中控制分子的构象。轴向手性喹啉衍生物很少以对映选择性催化方式合成，通过溴化反应可得到中等至良好的对映选择性，类似的方案也可实现对映选择性碘化。此外，这种催化反应允许通过使用单邻位取代的底物进行对映选择性控制，从而实现了高对映选择性下带有两个不同卤素基团的8-芳基喹啉衍生物的不对称合成。

  DOI：

  10.1002/chem.201701707

文献信息

• Piperazine-piperidine antagonists and agonists of the 5-HT1A receptor
  申请人：Asselin Magda

  公开号：US20070027160A1

  公开（公告）日：2007-02-01

  The present invention relates to novel piperazine-piperidine compounds. The compounds are useful as 5-HT 1A binding agents, particularly as 5-HT 1A receptor antagonists and agonists. These compounds are useful in treating central nervous system disorders, such as cognition disorders, anxiety disorders, depression and sexual dysfunction.

  本发明涉及新型哌嗪-哌啶化合物。这些化合物可用作5-HT1A结合剂，特别是作为5-HT1A受体拮抗剂和激动剂。这些化合物在治疗中枢神经系统疾病方面很有用，如认知障碍、焦虑症、抑郁症和性功能障碍。
• [EN] NITROGENOUS HETEROCYCLIC DERIVATIVES AND THEIR APPLICATION IN DRUGS<br/>[FR] DÉRIVÉS HÉTÉROCYCLIQUES AZOTÉS ET LEUR APPLICATION DANS DES MÉDICAMENTS
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2015090232A1

  公开（公告）日：2015-06-25

  The present invention relates to the field of medicine, provided herein are novel nitrogenous heterocyclic compounds, their preparation methods and their uses as drugs, especially for treatment and prevention of tissue fibrosis. Also provided herein are pharmaceutically acceptable compositions comprising the nitrogenous heterocyclic compounds and the uses of the compositions in the treatment of human or animal tissue fibrosis, especially for human or animal renal interstitial fibrosis, glomerular sclerosis, liver fibrosis, pulmonary fibrosis, IPF, peritoneal fibrosis, myocardial fibrosis, dermatofibrosis, postsurgical adhesion, benign prostatic hyperplasia, skeletal muscle fibrosis, scleroderma, multiple sclerosis, pancreatic fibrosis, cirrhosis, myosarcoma, neurofibroma, pulmonary interstitial fibrosis, diabetic nephropathy, alzheimer disease or vascular fibrosis.

  本发明涉及医学领域，提供了新颖的含氮杂环化合物，其制备方法以及作为药物的用途，特别是用于治疗和预防组织纤维化。本文还提供了包含这些含氮杂环化合物的药用可接受组合物，以及这些组合物在治疗人类或动物组织纤维化方面的用途，特别是用于人类或动物肾间质纤维化、肾小球硬化、肝纤维化、肺纤维化、IPF、腹膜纤维化、心肌纤维化、皮肤纤维化、术后粘连、良性前列腺增生、骨骼肌纤维化、硬皮病、多发性硬化、胰腺纤维化、肝硬化、肌肉肉瘤、神经纤维瘤、肺间质纤维化、糖尿病肾病、阿尔茨海默病或血管纤维化。
• Auxiliary-Directed C(sp³ )−H Arylation by Synergistic Photoredox and Palladium Catalysis
  作者：Milena L. Czyz、David W. Lupton、Anastasios Polyzos

  DOI：10.1002/chem.201704045

  日期：2017.10.17

  Herein we describe the auxiliary‐directed arylation of unactivated C(sp3)−H bonds with aryldiazonium salts, which proceeds under synergistic photoredox and palladium catalysis. The site‐selective arylation of aliphatic amides with α‐quaternary centres is achieved with high selectivity for β‐methyl C(sp3)−H bonds. This operationally simple method is compatible with carbocyclic amides, a range of aryldiazonium

  在这里，我们描述了未活化的C（sp 3）-H键与芳基重氮盐的辅助定向芳基化，该芳基重氮盐在协同的光氧化还原和钯催化下进行。脂族酰胺具有α-季中心的位点选择性芳基化是通过对β-甲基C（sp 3）-H键的高选择性实现的。这种操作简单的方法与碳环酰胺，各种芳基重氮盐兼容，并在环境条件下进行。
• [EN] COMPOUNDS FOR BINDING PROPROTEIN CONVERTASE SUBTILISIN/KEXIN TYPE 9 (PCSK9)<br/>[FR] COMPOSÉS SE LIANT À LA PROPROTÉINE CONVERTASE SUBTILISINE/KEXINE DE TYPE 9 (PCSK9)
  申请人：PORTOLA PHARM INC

  公开号：WO2017147328A1

  公开（公告）日：2017-08-31

  The present disclosure relates to novel compounds, methods, and compositions capable of binding to PCSK9, thereby modulating PCSK9 proprotein convertase enzyme activity. The compounds of the disclosure include compounds Formula (I).

  本公开涉及与PCSK9结合的新化合物、方法和组合物，从而调节PCSK9前蛋白酶酶活性。本公开的化合物包括化合物式（I）。
• The Influence of the Quinoline Moiety on Direct Pd‐Catalyzed Arylation of Five‐Membered Heterocycles
  作者：Bogdan Štefane、Uroš Grošelj、Jurij Svete、Franc Požgan、Drago Kočar、Helena Brodnik Žugelj

  DOI：10.1002/ejoc.201800842

  日期：2019.1.23

  reactivity of C2‐quinoline‐substituted furan, thiophene and pyrrole derivatives in palladium‐catalyzed direct C–H arylation. The regioselectivity of the reaction was strongly influenced by site position of the attached five‐membered heterocycle thus giving rise to C3‐ and/or C5‐arylated products. Furthermore, the Hammett correlation performed on 5‐substituted‐8‐(furan‐2‐yl)quinolines indicates that a marginally

  本文中我们报道了在钯催化的直接CHH芳基化反应中，C2-喹啉取代的呋喃，噻吩和吡咯衍生物的反应性。反应的区域选择性受到连接的五元杂环的位置的强烈影响，因此产生了C3和/或C5芳基化产物。此外，对5-取代-8-（呋喃-2-基）喹啉进行的哈米特相关性表明，在决定速率的过渡态中会形成少量的正电荷，从而指向亲电子的金属化-去质子化反应机理。