8-溴-2-甲基喹啉 | 61047-43-6

• 物质功能分类: 医药中间体
• 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-2-甲基喹啉
• 中文别名: 2-甲基-8-溴喹啉；8-溴喹哪啶
• 英文名称: 8-bromo-2-methylquinoline
• 英文别名: 8-Brom-chinaldin
• CAS: 61047-43-6
• 化学式: C₁₀H₈BrN
• mdl: MFCD04966997
• 分子量: 222.084
• InChiKey: GQPRZSFQSOEDNV-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65℃
• 沸点：
  132°C/0.1mmHg(lit.)
• 密度：
  1.488

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H315,H319
• 储存条件：
  室温

SDS

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Section I.Chemical Product and Company Identification
Chemical Name 8-Bromo-2-methylquinoline
Portland OR
Synonym Quinoline, 8-bromo-2-methyl- (CA INDEX NAME);
8-Bromoquinaldine
Chemical Formula C10H8BrN
CAS Number 61047-43-6

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Section II. Composition and Information on Ingredients
Toxicology Data
Chemical Name CAS Number Percent (%) TLV/PEL
Min. 98.0 (GC, Not available. Not available.
8-Bromo-2-methylquinoline 61047-43-6
T)

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Section III. Hazards Identification
Acute Health Effects Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the
eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.
Chronic Health Effects CARCINOGENIC EFFECTS : Not available.
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.

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Section IV. First Aid Measures
Eye Contact Check for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15
minutes. Get medical attention.
Skin Contact In case of contact, immediately flush skin with plenty of water. Remove contaminated clothing and shoes. Wash clothing
before reuse. Thoroughly clean shoes before reuse. Get medical attention.
If the victim is not breathing, perform mouth-to-mouth resuscitation. Loosen tight clothing such as a collar, tie, belt or
Inhalation
waistband. If breathing is difficult, oxygen can be administered. Seek medical attention if respiration problems do not
improve.
INDUCE VOMITING by sticking finger in throat. Lower the head so that the vomit will not reenter the mouth and throat.
Ingestion
Loosen tight clothing such as a collar, tie, belt or waistband. If the victim is not breathing, perform mouth-to-mouth
resuscitation. Examine the lips and mouth to ascertain whether the tissues are damaged, a possible indication that the toxic
material was ingested; the absence of such signs, however, is not conclusive.

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Section V. Fire and Explosion Data
Not available.
May be combustible at high temperature. Auto-Ignition
Flammability
Flash Points Flammable Limits Not available.
Not available.
These products are toxic carbon oxides (CO, CO2), nitrogen oxides (NOx), halogenated compounds.
Combustion Products
Fire Hazards Not available.
Risks of explosion of the product in presence of mechanical impact: Not available.
Explosion Hazards
Risks of explosion of the product in presence of static discharge: Not available.
Fire Fighting Media
SMALL FIRE: Use DRY chemical powder.
LARGE FIRE: Use water spray, fog or foam. DO NOT use water jet.
and Instructions
Consult with local fire authorities before attempting large scale fire-fighting operations.
Continued on Next Page
8-Bromo-2-methylquinoline

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Section VI. Accidental Release Measures
Spill Cleanup Irritating material.
Use a shovel to put the material into a convenient waste disposal container. Consult federal, state, and/or local authorities for
Instructions
assistance on disposal.

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Section VII. Handling and Storage
Handling and Storage IRRITANT. Keep away from heat. Mechanical exhaust required. When not in use, tightly seal the container and store in a
dry, cool place. Avoid excessive heat and light. Do not breathe dust.
Information

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Section VIII. Exposure Controls/Personal Protection
Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended
Engineering Controls
exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants
below the exposure limit.
Splash goggles. Lab coat. Dust respirator. Boots. Gloves. Suggested protective clothing might not be sufficient; consult a
Personal Protection
specialist BEFORE handling this product. Be sure to use a MSHA/NIOSH approved respirator or equivalent.
Exposure Limits Not available.

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Section IX. Physical and Chemical Properties
Physical state @ 20°C Solid. (Crystal, powder. White, slightly Solubility
Not available.
pale yellow.)
Not available.
Specific Gravity
Molecular Weight 222.08 Partition Coefficient Not available.
Boiling Point 132°C (269.6°F) @ 0.1 mmHg Vapor Pressure Not applicable.
Melting Point 68°C (154.4°F) Vapor Density Not available.
Not available. Not available.
Refractive Index Volatility
Critical Temperature Not available. Odor Not available.
Not available. Not available.
Viscosity Taste

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Section X. Stability and Reactivity Data
Stability

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This material is stable if stored under proper conditions. (See Section VII for instructions)
Conditions of Instability Avoid excessive heat and light.
Incompatibilities Not available.

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Section XI. Toxicological Information
RTECS Number Not available.
Eye Contact. Ingestion. Inhalation.
Routes of Exposure
Not available.
Toxicity Data
CARCINOGENIC EFFECTS : Not available.
Chronic Toxic Effects
MUTAGENIC EFFECTS : Not available.
TERATOGENIC EFFECTS : Not available.
DEVELOPMENTAL TOXICITY: Not available.
Repeated or prolonged exposure to this compound is not known to aggravate existing medical conditions.
Irritating to eyes and skin on contact. Inhalation causes irritation of the lungs and respiratory system. Inflammation of the eye
Acute Toxic Effects
is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or,
occasionally, blistering.
Follow safe industrial hygiene practices and always wear proper protective equipment when handling this compound.

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Section XII. Ecological Information
Ecotoxicity Not available.
Not available.
Environmental Fate
Continued on Next Page
8-Bromo-2-methylquinoline

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Section XIII. Disposal Considerations
Waste Disposal Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system. Observe all
federal, state and local regulations when disposing of the substance.

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Section XIV. Transport Information
Not a DOT controlled material (United States).
DOT Classification
PIN Number Not applicable.
Proper Shipping Name Not applicable.
Packing Group (PG) Not applicable.
DOT Pictograms

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Section XV. Other Regulatory Information and Pictograms
TSCA Chemical Inventory This product is NOT on the EPA Toxic Substances Control Act (TSCA) inventory. The following notices are required by 40
CFR 720.36 (C) for those products not on the inventory list:
(EPA)
(i) These products are supplied solely for use in research and development by or under the supervision of a technically
qualified individual as defined in 40 CFR 720.0 et sec.
(ii) The health risks of these products have not been fully determined. Any information that is or becomes available will be
supplied on an MSDS sheet.
WHMIS Classification Not available.
(Canada)
EINECS Number (EEC) Not available.
EEC Risk Statements R36/37/38- Irritating to eyes, respiratory system and skin.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

8-溴-2-甲基喹啉是喹啉类衍生物，可用于制备医药中间体。

反应信息

• 作为反应物：
  描述：

  8-溴-2-甲基喹啉 在 copper acetylacetonate 、 N1,N2-bis(4-hydroxy-2,6-dimethylphenyl)oxalamide 、 水 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 以95%的产率得到8-羟基喹哪啶
  参考文献：
  名称：

  (杂)芳基卤化物在温和条件下的铜催化羟基化

  摘要：

  Cu(acac)2 和 N,N'-双(4-羟基-2,6-二甲基苯基)草酰胺 (BHMPO) 的组合为（杂）芳基卤化物的羟基化提供了强大的催化系统。各种带有给电子或吸电子基团的（杂）芳基氯化物在 130 °C 下均能很好地进行，以良好到极好的产率提供相应的酚类和羟基化杂芳烃。当使用反应性更强的（杂）芳基溴化物和碘化物时，羟基化反应在相对较低的温度（分别为 80 和 60 °C）下在低催化负载（0.5 mol% Cu）下完成。

  DOI：

  10.1021/jacs.6b08114
• 作为产物：
  描述：

  8-bromo-2-methylquinoline*ZnCl2 complex 在 氨 作用下， 以 水 为溶剂， 以39%的产率得到8-溴-2-甲基喹啉
  参考文献：
  名称：

  甲硅烷基吡啶和喹啉阳离子的手性记忆

  摘要：

  已经制备了吡啶和喹啉稳定的甲硅烷基阳离子，并使用 1H、13C、15N、29Si 和 1H DOSY NMR 以及 X 射线衍射研究明确指定了它们在凝聚相中的结构。因此，固态结构在两种情况下都显示出通过 N-Si 相互作用和形成高度应变的 4 元环系统使阳离子硅中心稳定。还建立了这些杂环稳定的甲硅烷基阳离子中硅原子的手性记忆，根据杂环的性质导致不同水平的选择性。通过 DFT 计算获得的起始硅烷的最低能量构象，

  DOI：

  10.1021/jacs.9b11704

文献信息

• Ligand-Free, Quinoline N-Assisted Copper-Catalyzed Nitrene Transfer Reaction To Synthesize 8-Quinolylsulfimides
  作者：Xinsheng Xiao、Sanping Huang、Shanshan Tang、Guokai Jia、Guangchuan Ou、Yangyan Li

  DOI：10.1021/acs.joc.9b00281

  日期：2019.6.21

  An efficient copper-catalyzed, quinolyl N-directed nitrene transfer reaction to 8-quinolylsulfides was described. A variety of 8-quinolylsulfimides with different functional groups were synthesized in moderate to high yields. The obtained 8-quinolylsulfimides were proved to be promising novel type of bidentate ligands in Pd(II)-catalyzed allylic alkylation.

  描述了一种有效的铜催化的，喹啉基N定向的腈转移反应生成8-喹啉基硫化物的方法。以中等至高收率合成了具有不同官能团的多种8-喹啉基亚磺酰亚胺。事实证明，在Pd（II）催化的烯丙基烷基化反应中，所获得的8-喹啉硫磺酰亚胺是有前途的新型二齿配体。
• Highly Enantioselective Iron-Catalyzed <i>cis</i> -Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an Fe^III -OOH Reactive Intermediate
  作者：Chao Zang、Yungen Liu、Zhen-Jiang Xu、Chun-Wai Tse、Xiangguo Guan、Jinhu Wei、Jie-Sheng Huang、Chi-Ming Che

  DOI：10.1002/anie.201603410

  日期：2016.8.22

  catalysts for highly enantioselective asymmetric cis‐dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′‐dimethyl‐N,N′‐bis(2‐methyl‐8‐quinolyl)‐cyclohexane‐1,2‐diamine) as a catalyst, cis‐diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2 as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2”

  开发具有良好底物范围的烯烃的高对映选择性不对称顺二羟基化（AD）的环境友好型催化剂仍然是一个挑战。通过使用[Fe II（L）（OTf）2 ]（L = N，N'-二甲基-N，N'-双（2-甲基-8-喹啉基）-环己烷-1,2-二胺）作为催化剂，在以H 2 O 2为氧化剂的烯烃和数量有限的烯烃的AD中，已实现了高达99.8％ee的顺式二醇和85％的分离产率。该“ [Fe II（L）（OTf）2 ] + H 2 O 2”方法适用于（E）-烯烃和末端烯烃（24个实例，ee大于80％，最大1 g）。机理研究包括18种O-标记，UV / Vis，EPR，ESI-MS分析和DFT计算，为手性Fe III- OOH活性物种参与两个C-O键的对映选择性形成提供了证据。
• <scp>Rh‐Catalyzed</scp> Formal [3+2] Cyclization for the Synthesis of <scp>5‐Aryl</scp> ‐2‐(quinolin‐2‐yl)oxazoles and Its Applications in Metal Ions Probes
  作者：Tongtong Zhou、Xinwei He、Youpeng Zuo、Yuhao Wu、Wangcheng Hu、Shiwen Zhang、Jiahui Duan、Yongjia Shang

  DOI：10.1002/cjoc.202000454

  日期：2021.3

  efficient strategy for the synthesis of 5‐aryl‐2‐(quinolin‐2‐yl)oxazoles via rhodium‐catalyzed formal [3+2] cyclization of 4‐aryl‐1‐tosyl‐1H‐1,2,3‐triazoles with quinoline‐2‐carbaldehydes has been described. The protocol employs mild conditions and offers good yields of diverse 2,5‐aryloxazole derivatives with a broad reaction scope. It is amenable to gram‐scale synthesis and easily transformation.

  通过铑催化4-芳基-1-甲苯磺酰基-1 H 1,2的正式[3 + 2]环化反应，合成5-芳基-2-（喹啉-2-基）恶唑的简便有效方法，已经描述了3-三唑与喹啉-2-甲醛。该方案采用温和的条件，并具有良好的反应范围，可提供各种2,5-芳基恶唑衍生物的良好收率。它适用于克级合成和轻松转换。此外，这种5-芳基-2-（喹啉-2-基）恶唑骨架确实是一种新的荧光团，并且还研究了其在金属离子探针中的应用，并显示了对汞离子的荧光响应。
• Oxalohydrazide Ligands for Copper‐Catalyzed C−O Coupling Reactions with High Turnover Numbers
  作者：Ritwika Ray、John F. Hartwig

  DOI：10.1002/anie.202015654

  日期：2021.4.6

  long‐lived copper catalysts for couplings that form the C−O bonds in biaryl ethers. These Cu‐catalyzed coupling of phenols with aryl bromides occurred with turnovers up to 8000, a value which is nearly two orders of magnitude higher than those of prior couplings to form biaryl ethers and nearly an order of magnitude higher than those of any prior copper‐catalyzed coupling of aryl bromides and chlorides

  在这里，我们报道了一类基于草酰肼核心和N-氨基吡咯和N-氨基吲哚单元的配体，它们生成长寿命的铜催化剂，用于在联芳醚中形成CO键的偶联。这些铜催化的酚类与芳基溴化物的偶联反应的转化率高达 8000，该值比之前形成联芳基醚的偶联反应高出近两个数量级，并且比任何现有的铜催化偶联反应高出近一个数量级。芳基溴和氯化物的催化偶联。该配体还产生了催化芳基氯与苯酚的偶联以及芳基溴和芳基碘与伯苄醇和脂肪醇的偶联的铜体系。可耐受多种官能团，包括腈、卤化物、醚、酮、胺、酯、酰胺、乙烯基芳烃、醇和硼酸酯，并且与药物相关结构中的芳基溴发生反应。
• Structure-activity relationships, biological evaluation and structural studies of novel pyrrolonaphthoxazepines as antitumor agents
  作者：Margherita Brindisi、Cristina Ulivieri、Gloria Alfano、Sandra Gemma、Francisco de Asís Balaguer、Tuhina Khan、Alessandro Grillo、Giulia Chemi、Grégory Menchon、Andrea E. Prota、Natacha Olieric、Daniel Lucena-Agell、Isabel Barasoain、J. Fernando Diaz、Angela Nebbioso、Mariarosaria Conte、Ludovica Lopresti、Stefania Magnano、Rebecca Amet、Paula Kinsella、Daniela M. Zisterer、Ola Ibrahim、Jeff O'Sullivan、Lucia Morbidelli、Roberta Spaccapelo、Cosima Baldari、Stefania Butini、Ettore Novellino、Giuseppe Campiani、Lucia Altucci、Michel O. Steinmetz、Simone Brogi

  DOI：10.1016/j.ejmech.2018.11.004

  日期：2019.1

  efforts we developed improved pyrrolonaphthoxazepines antitumor agents and their mode of action at the molecular level was elucidated. Compound 6j, one of the most potent analogues, was confirmed by X-ray as a colchicine-site MTA. A comprehensive structural investigation was performed for a complete elucidation of the structure-activity relationships. Selected pyrrolonaphthoxazepines were evaluated for

  微管靶向剂（MTA）是一类临床上成功的抗癌药物。对MTA的多药耐药性的出现要求开发具有多种机械性能的新型MTA。苯并a庚因最近被确定为一类新型的MTA。这些抗癌剂的抗肿瘤活性得到了彻底的表征，尽管它们的确切作用机理仍然难以捉摸。结合化学，生化，细胞，生物信息学和结构方面的努力，我们开发了改进的吡咯并萘并氧杂氮杂卓类抗肿瘤药，并阐明了它们在分子水平上的作用方式。化合物6jX射线证实它是最有效的类似物之一，是秋水仙碱的MTA。为了全面阐明结构-活性关系，进行了全面的结构研究。评价了选定的吡咯并萘并氧杂氮杂卓类化合物对多种癌细胞（包括耐多药细胞系）的细胞周期，凋亡和分化的影响。我们的结果将化合物6j定义为开发用于治疗耐药性肿瘤的有效化合物的潜在有用的最佳选择。