6-溴-2-氯喹啉 | 1810-71-5

• 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: 6-溴-2-氯喹啉
• 中文别名: 6-溴喹啉-2(1H)-酮；2-氯-6-溴喹啉；6-溴-2-氯-喹林
• 英文名称: 6-bromo-2-chloroquinoline
• 英文别名: 2-chloro-6-bromoquinoline
• CAS: 1810-71-5
• 化学式: C₉H₅BrClN
• mdl: MFCD04115272
• 分子量: 242.502
• InChiKey: YXRDWUJAJLDABJ-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150℃
• 沸点：
  325.7±22.0 °C(Predicted)
• 密度：
  1.673±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿和甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

安全信息

• 危险品标志：
  T
• 安全说明：
  S45
• 危险类别码：
  R25
• 海关编码：
  2933499090
• 储存条件：
  存储温度：0-10°C；应存放在惰性气体中；避免与空气接触并防止加热。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
6-Bromo-2-chloroquinoline
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
6-Bromo-2-chloroquinoline
Ingredient name:
CAS number: 1810-71-5

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H5BrClN
Molecular weight: 242.5

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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 chloride, 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

制备方法与用途

化学性质

6-溴-2-氯喹啉是一种具有强烈臭味且无色、吸湿性强的杂环芳香性有机化合物。

用途

该物质是冶金、染料、聚合物以及农用化学品工业的重要中间体，同时也能用作消毒剂、防腐剂及溶剂。值得注意的是，6-溴-2-氯喹啉具有毒性。

合成方法 步骤1：制备6-溴喹啉-2（1H）-酮

将33（24.98 g，82.7 mmol）与AlCl3（33.10 g，248.2 mmol）在研钵中研磨成亲密混合物。随后，将反应混合物转移到圆底烧瓶中，并用加热枪迅速加热至熔化状态，在110℃下保持1.5小时。冷却后，将混合物用水淬火、过滤并用冷水洗涤，干燥后的产物呈粉红色粉末状，熔点为272-274℃（19.03 g，100%）。此步骤无需进一步纯化。

步骤2：制备6-溴-2-氯喹啉

将8.52 g（38.0 mmol）的产物与40 mL三氯氧磷混合，在回流加热下反应1小时。冷却后，用减压蒸发除去多余试剂，并用水淬火剩余混合物。过滤固体并用水洗涤，再从己烷中重结晶以获得目标化合物，呈淡粉色粉末状，熔点为157-158℃（5.34 g，58%）。

图展示了6-溴-2-氯喹啉的结构式。

反应信息

• 作为反应物：
  描述：

  6-溴-2-氯喹啉 在 盐酸 、 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 6-甲基喹啉-2(1h)-酮
  参考文献：
  名称：

  可见光照射诱导2(1H)-喹诺酮类的对映选择性分子间[2+2]光环加成反应

  摘要：

  在手性噻吨酮催化剂 (10 mol%) 存在下，标题化合物在 λ = 419 nm 处与缺电子烯烃进行了干净的分子间 [2 + 2] 光环加成反应。该反应不仅具有出色的区域选择性和非对映选择性，而且还提供了对映体显着过量（高达 95% ee）的相应环丁烷产物。反应成功的关键是喹诺酮和催化剂之间的两点氢键，能够实现高效的能量转移和高对映面分化。初步工作表明，该过程可以使用太阳辐射，并且底物范围可以进一步扩展到异喹诺酮类药物。

  DOI：

  10.1021/jacs.6b03221
• 作为产物：
  描述：

  4 -溴- 2 - 碘苯甲胺 在 N-甲基吡咯烷酮 、 palladium diacetate 、 三正丁胺 、 三氯氧磷 作用下， 以 乙二醇 为溶剂， 反应 0.33h， 生成 6-溴-2-氯喹啉
  参考文献：
  名称：

  Development of 6-substituted indolylquinolinones as potent Chek1 kinase inhibitors

  摘要：

  Through a comparison of X-ray co-crystallographic data for 1 and 2 in the Chek1 active site, it was hypothesized that the affinity of the indolylquinolinone series (2) for Chek1 kinase would be improved via C6 substitution into the hydrophobic region I (HI) pocket. An efficient route to 6-bromo-3-indolyl-quinolinone (9) was developed, and this series was rapidly optimized for potency by modification at C6. A general trend was observed among these low nanomolar Chek1 inhibitors that compounds with multiple basic amines, or elevated polar surface area (PSA) exhibited poor cell potency. Minimization of these parameters (basic amines, PSA) resulted in Chek1 inhibitors with improved cell potency, and preliminary pharmacokinetic data are presented for several of these compounds.

  DOI：

  10.1016/j.bmcl.2006.08.053
• 作为试剂：
  描述：

  8-methyl-2-piperazine-1-yl-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinoline 在 6-溴-2-氯喹啉 作用下， 反应 10.0h， 生成 (2S)-2-{[4-(6-bromoquinolin-2-yl)piperazin-1-yl]methyl}-8-methyl-2,3-dihydro[1,4]dioxino[2,3-f]quinoline
  参考文献：
  名称：

  [EN] ANTIDEPRESSANT ARYLPIPERAZINE DERIVATIVES OF HETEROCYCLE-FUSED BENZODIOXANS
  [FR] DERIVES ARYLPIPERAZINES ANTIDEPRESSEURS DE BENZODIOXANES A FUSION HETEROCYCLIQUE

  摘要：

  公式I的化合物对治疗抑郁症（包括但不限于重性抑郁障碍、儿童抑郁症和心境恶劣障碍）、焦虑症、恐慌障碍、创伤后应激障碍、经前期情感障碍（也称为经前综合征）、注意力缺陷障碍（伴有和不伴有多动症）、强迫症、社交焦虑障碍、广泛性焦虑障碍、肥胖、厌食症和暴食症等进食障碍、血管运动性潮红、可卡因和酒精成瘾、性功能障碍及相关疾病方面具有用处。

  公开号：

  WO2004024731A1

文献信息

• [EN] FUSED 1,4-DIHYDRODIOXIN DERIVATIVES AS INHIBITORS OF HEAT SHOCK TRANSCRIPTION FACTOR 1<br/>[FR] DÉRIVÉS DE 1,4-DIHYDRODIOXINE FUSIONNÉS À UTILISER EN TANT QU'INHIBITEURS DE FACTEUR DE TRANSCRIPTION 1 DU CHOC THERMIQUE
  申请人：CANCER REC TECH LTD

  公开号：WO2015049535A1

  公开（公告）日：2015-04-09

  The present invention relates to compounds of formula I wherein A1, A2 R4 and Q are as defined herein. The compounds of the present invention are inhibitors of heat shock factor 1 (HSF1). In particular, the present invention relates to the use of these compounds as therapeutic agents for the treatment and/or prevention of proliferative diseases, such as cancer. The present invention also relates to processes for the preparation of these compounds, and to pharmaceutical compositions comprising them.

  本发明涉及式I的化合物，其中A1、A2、R4和Q如本文所定义。本发明的化合物是热休克因子1（HSF1）的抑制剂。具体来说，本发明涉及将这些化合物用作治疗和/或预防增殖性疾病，如癌症的治疗剂。本发明还涉及制备这些化合物的方法，以及包含它们的药物组合物。
• Synthesis of 3,5-Disubstituted Isoxazoles Containing Privileged Substructures with a Diverse Display of Polar Surface Area
  作者：Mingi Kim、Yoon Soo Hwang、Wansang Cho、Seung Bum Park

  DOI：10.1021/acscombsci.7b00032

  日期：2017.6.12

  substituents which uniquely display polar surface area in a diverse manner. A library of 3,5-disubstituted isoxazoles were systematically prepared via 1,3-dipolar cycloaddition of alkynes with nitrile oxides prepared by two complementary synthetic routes; method A utilized a halogenating agent with a base and method B utilized a hypervalent iodine reagent. Through the biological evaluation of corresponding

  我们设计并合成了3,5-二取代异恶唑的分子框架，其中包含具有各种取代基的特权子结构，这些取代基以多种方式唯一显示极性表面积。通过炔烃的1，3-偶极环加成与通过两种互补合成途径制备的腈氧化物系统地制备了3，5-二取代异恶唑的文库。方法A使用带有碱的卤化剂，方法B使用高价碘试剂。通过三种独立的表型分析方法对相应的异恶唑进行生物学评估，根据特权亚结构和取代基的类型显示了不同的生物活性模式。
• 2-AMINOQUINOLINES
  申请人：Kolczewski Sabine

  公开号：US20090227583A1

  公开（公告）日：2009-09-10

  The present invention relates to compounds of formula (I) wherein A, R 1 , R 2 , R 3 , R 4 , and R 5 are as described herein, pharmaceutical compositions containing them, and methods for their manufacture. These compounds are 5-HT 5A receptor antagonistsand are useful in the prevention and/or treatment of depression, anxiety disorders, schizophrenia, panic disorders, agoraphobia, social phobia, obsessive compulsive disorders, post-traumatic stress disorders, pain, memory disorders, dementia, disorders of eating behaviors, sexual dysfunction, sleep disorders, abuse of drugs, motor disorders such as Parkinson's disease, psychiatric disorders or gastrointestinal disorders.

  本发明涉及式(I)的化合物， 其中A，R1，R2，R3，R4和R5如本文所述，含有它们的药物组合物，以及其制备方法。这些化合物是5-HT5A受体拮抗剂，可用于预防和/或治疗抑郁症、焦虑障碍、精神分裂症、恐慌障碍、广场恐惧症、社交恐惧症、强迫症、创伤后应激障碍、疼痛、记忆障碍、痴呆症、进食行为障碍、性功能障碍、睡眠障碍、药物滥用、帕金森病等运动障碍、精神障碍或胃肠道障碍的治疗。
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2011059850A1

  公开（公告）日：2011-05-19

  The present disclosure relates to methods for making compounds useful in the treatment of Hepatitis C virus (HCV) infection.

  本公开涉及制备用于治疗丙型肝炎病毒（HCV）感染的化合物的方法。
• [EN] BUMPED KINASE INHIBITOR COMPOSITIONS AND METHODS FOR TREATING CANCER<br/>[FR] COMPOSITIONS D'INHIBITEUR DE KINASE À BOSSES ET MÉTHODES DE TRAITEMENT DU CANCER
  申请人：UNIV WASHINGTON

  公开号：WO2016123151A1

  公开（公告）日：2016-08-04

  The present disclosure is generally directed to bumped kinase inhibitor (BKI) compositions and methods for treating cancer.

  本公开涉及通常用于治疗癌症的凸起激酶抑制剂（BKI）组合物和方法。