5,8-二溴喹啉 | 81278-86-6

• 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: 5,8-二溴喹啉
• 英文名称: 5,8-Dibromoquinoline
• 英文别名: 5,8-Dibrom-chinolin
• CAS: 81278-86-6
• 化学式: C₉H₅Br₂N
• mdl: MFCD04966994
• 分子量: 286.953
• InChiKey: LCSHATKNSDVDRY-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  347.9±22.0 °C(Predicted)
• 密度：
  1.923±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  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：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335
• 储存条件：
  室温且干燥环境中保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5,8-Dibromoquinoline
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: 5,8-Dibromoquinoline
CAS number: 81278-86-6

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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: C9H5Br2N
Molecular weight: 287.0

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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

制备方法与用途

应用

5,8-二溴喹啉是一种杂环有机物，可作为医药中间体。

反应信息

• 作为反应物：
  描述：

  5,8-二溴喹啉 在 盐酸 、 乙醇 、 硫酸 、 硝酸 、 tin(ll) chloride 作用下， 生成 5,8-dibromo-[6]quinolylamine
  参考文献：
  名称：

  Claus; Geisler, Journal fur praktische Chemie (Leipzig 1954), 1889, vol. <2> 40, p. 380

  摘要：

  DOI：
• 作为产物：
  描述：

  喹啉 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 反应 8.0h， 以61%的产率得到5,8-二溴喹啉
  参考文献：
  名称：

  Bromination of Isoquinoline, Quinoline, Quinazoline and Quinoxaline in Strong Acid

  摘要：

  苯并吡嗪和苯并二嗪的溴化反应通常得到多种产物混合物。本文中，我们展示了异喹啉（1）可在浓硫酸中使用NBS或在三氟甲磺酸中使用N,N’-二溴异氰尿酸（DBI）进行区域选择性单溴化，得到5-溴异喹啉（2）。研究发现，溴化反应对溴化剂、酸、温度和浓度的选择非常敏感。喹啉、喹唑啉和喹喔啉亦可进行类似溴化，尽管其区域选择性不如异喹啉强烈。

  DOI：

  10.1055/s-2002-19314

文献信息

• [EN] SULFONE DERIVATIVES AND THEIR USE AS PKM2 MODULATORS FOR THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE SULFONE ET LEUR UTILISATION EN TANT QUE MODULATEURS DE PKM2 POUR LE TRAITEMENT DU CANCER
  申请人：LUPIN LTD

  公开号：WO2013005157A1

  公开（公告）日：2013-01-10

  Provided herein is novel compound of the general formula (I), its tautomeric forms, its stereoisomers, its analogs, its prodrugs, its isotopes, its N- oxides, its metabolites, its pharmaceutically acceptable salts, its polymorphs, its solvates, its optical isomers, its clathrates, its co-crystals, its combinations with suitable medicament and pharmaceutical compositions comprising the same. Also provided is method of treating a disease responsive to activation of human PKM2 by administration of said compound and its use as PKM2 modulator in various pathological conditions.

  提供了一种通用公式（I）的新型化合物，其互变异构体，立体异构体，类似物，前药，同位素，N-氧化物，代谢物，药用可接受盐，多态性，溶剂化物，光学异构体，包合物，共晶，与适宜药物的组合以及包含同一的药物组合物。还提供了一种通过施用所述化合物来治疗对人类PKM2激活有反应的疾病的方法，以及将其用作各种病理条件下的PKM2调节剂。
• 作为URAT1抑制剂的化合物
  申请人：江苏艾立康药业股份有限公司

  公开号：CN107814795B

  公开（公告）日：2020-12-18

  本发明提供了具有通式（I）的一系列化合物，其中，n选自1、2或3；X选自O或S；Q选自C或N；R选自H、卤素、‑C1‑6烷基。所述化合物可以作为URAT1抑制剂，用于治疗高尿酸血症和痛风。
• Preparation of Nitrogen-Containing Bis(heteroaryl)iodonium Salts
  作者：Peter J. Stang、Bogdan Olenyuk、Kuanchiang Chen

  DOI：10.1055/s-1995-4023

  日期：1995.8

  Hitherto unknown nitrogen-containing bis(heteroaryl)iodonium chlorides are prepared by the reaction of the appropriate aryllithium with β-chlorovinyliodonium dichloride. The bis(heteroaryl)iodonium chlorides may be readily converted to the corresponding triflate salts via reaction with trimethylsilyl triflate.

  迄今为止未知的含氮双（异芳基）碘鎓氯化物是通过相应的芳基锂与β-氯乙烯碘鎓二氯化物反应制备的。双（异芳基）碘鎓氯化物可以通过与三甲基硅基三氟甲磺酸反应，方便地转换为相应的三氟甲磺酸盐。
• HETEROCYCLIC AMINE DERIVATIVES
  申请人：Galley Guido

  公开号：US20120245172A1

  公开（公告）日：2012-09-27

  The present invention relates to compounds of formula I wherein A, B, X, Y, Ar, R 1 , R 2 , R′, m and n are as defined herein and to pharmaceutical active acid addition salts thereof. Compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds can be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及式I的化合物，其中A、B、X、Y、Ar、R1、R2、R′、m和n的定义如本文所述，并且涉及其药用活性酸盐。式I的化合物对痕量胺相关受体（TAARs）具有良好的亲和力，特别是对TAAR1。这些化合物可用于治疗抑郁症、焦虑障碍、双相情感障碍、注意力缺陷多动障碍（ADHD）、与压力相关的障碍、精神分裂症等精神障碍、帕金森病等神经系统疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用、以及代谢障碍如进食障碍、糖尿病、糖尿病并发症、肥胖症、脂质代谢异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍、以及心血管疾病。
• [EN] HETEROCYCLIC AMINE DERIVATIVES<br/>[FR] DÉRIVÉS D'AMINES HÉTÉROCYCLIQUES
  申请人：HOFFMANN LA ROCHE

  公开号：WO2012126922A1

  公开（公告）日：2012-09-27

  The present invention relates to compounds of formula (I) wherein R1 is hydrogen, lower alkyl, halogen, lower alkyl substituted by halogen, lower alkoxy, lower alkoxy substituted by halogen, cyano, nitro, C3-6-cycloalkyl, -CH2-C3-6-cycloalkyl, -O-CH2-C3-6-cycloalkyl, -O-(CH2)2-O-lower alkyl, S(O)2CH3, SF5, -C(O)NH-lower alkyl, phenyl, -O-pyrimidinyl, optionally substituted by lower alkoxy substituted by halogen, or is benzyl, oxetanyl or furanyl; m Ar is aryl or heteroaryl, selected from the group consisting of phenyl, naphthyl, pyrimidinyl, pyridinyl, benzothiazolyl, quinolinyl, quinazolinyl, benzo[d][1.3]dioxolyl, 5,6,7,8- tetrahydro-quinazolinyl, pyrazolyl, pyrazinyl, pyridazinyl, or 1,3,4-oxadiazolyl; Y is a bond, -CH2-, -CH2CH2-, -CH(CF3)- or -CH(CH3)-; R2 is hydrogen or lower alkyl; A is CR or N; and R is hydrogen, cyano, halogen or lower alkyl; R' is hydrogen or halogen; with the proviso that when R' is halogen, then A is CH; B is CH or N; n is 0, 1 or 2; X is a bond, -CH2- or -O-; pharmaceutical active acid addition salts thereof. It has now been found that the compounds of formula I have a good affinity to the trace amine associated receptors (TAARs), especially for TAAR1. The compounds may be used for the treatment of depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder (ADHD), stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders.

  本发明涉及以下式（I）的化合物，其中R1是氢、低碳基、卤素、被卤素取代的低碳基、低烷氧基、被卤素取代的低烷氧基、氰基、硝基、C3-6环烷基、-CH2-C3-6环烷基、-O-CH2-C3-6环烷基、-O-(CH2)2-O-低碳基、S(O)2CH3、SF5、-C(O)NH-低碳基、苯基、-O-嘧啶基，或是被低烷氧基取代的被卤素取代的苯基、或者是苄基、氧杂环戊二烯基或呋喃基；m Ar是芳基或杂芳基，选自苯基、萘基、嘧啶基、吡啶基、苯并噻唑基、喹啉基、喹唑啉基、苯并[d][1.3]二噁基、5,6,7,8-四氢喹唑啉基、吡唑基、吡嗪基、吡啶啉基或1,3,4-噁二唑基；Y是键、-CH2-、-CH2CH2-、-CH(CF3)-或-CH(CH3)-；R2是氢或低碳基；A是CR或N；R是氢、氰基、卤素或低碳基；R'是氢或卤素；但是如果R'是卤素，则A是CH；B是CH或N；n是0、1或2；X是键、-CH2-或-O-；以及它们的药用活性酸盐。现已发现，式I的化合物对痕量胺相关受体（TAARs）具有良好的亲和力，特别是对TAAR1。这些化合物可用于治疗抑郁症、焦虑障碍、躁郁症、注意力缺陷多动障碍（ADHD）、与压力有关的障碍、精神分裂症等精神障碍、帕金森病等神经系统疾病、阿尔茨海默病等神经退行性疾病、癫痫、偏头痛、高血压、物质滥用以及代谢障碍，如进食障碍、糖尿病、糖尿病并发症、肥胖症、脂质代谢异常、能量消耗和吸收障碍、体温稳态障碍、睡眠和昼夜节律障碍，以及心血管疾病。