5,7-二溴-8-甲氧基喹啉 | 17012-49-6

• 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: 5,7-二溴-8-甲氧基喹啉
• 中文别名: 5.7-二溴-8-甲氧基喹啉
• 英文名称: 5,7-dibromo-8-methoxyquinoline
• 英文别名: 5,7-Dibrom-8-methoxy-chinolin
• CAS: 17012-49-6
• 化学式: C₁₀H₇Br₂NO
• 分子量: 316.98
• InChiKey: IJANXCJVULGZRF-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C
• 沸点：
  380.2±37.0 °C(Predicted)
• 密度：
  1.830±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5,7-Dibromo-8-methoxyquinoline
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: 5,7-Dibromo-8-methoxyquinoline
CAS number: 17012-49-6

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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: C10H7Br2NO
Molecular weight: 317.0

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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

反应信息

• 作为反应物：
  描述：

  5,7-二溴-8-甲氧基喹啉 在 萘 、 四丁基氟化铵 、 lithium 、 potassium carbonate 、 苯基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 丙酮 为溶剂， 反应 7.0h， 生成 3,4-bis(7',8'-dimethoxyquinolin-5'-yl)pyrrole
  参考文献：
  名称：

  Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core

  摘要：

  Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4-dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respectable cytotoxicity and resensitize multidrug resistant (MDR) cancer cell lines at non-toxic concentrations. Cytotoxicity and MDR reversal can be efficiently uncoupled by per-O-methylation of the peripheral hydroxyl groups. For the storniamide core structure 9 it is demonstrated that this chemical modification goes hand in hand with a complete loss of the DNA-cleaving capacity of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00637-3
• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 、 碘甲烷 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 四氢呋喃 为溶剂， 反应 35.0h， 以90%的产率得到5,7-二溴-8-甲氧基喹啉
  参考文献：
  名称：

  Synthesis of Substituted 8-Methoxyquinolines by Regioselective Bromine-Lithium Exchange of 5,7-Dihalo-8-methoxyquinolines and 7-Bromo-8-methoxyquinoline

  摘要：

  苯基锂与7-溴-8-甲氧基喹啉、5,7-二溴-8-甲氧基喹啉及5,7-二碘-8-甲氧基喹啉的反应已被研究。因此，7-溴-8-甲氧基喹啉的溴锂交换生成7-锂代-8-甲氧基喹啉，其与多种亲电试剂反应得到7-取代-8-甲氧基喹啉3a-e。同样的步骤也应用于5,7-二溴-8-甲氧基喹啉，由于反应的高度位选择性，得到了7-取代的5-溴-8-甲氧基喹啉4a-f；其中一种用于制备吡啶并吡喃喹啉。

  DOI：

  10.1055/s-1995-4053

文献信息

• [EN] NEUROPROTECTIVE AND NEURO-RESTORATIVE IRON CHELATORS AND MONOAMINE OXIDASE INHIBITORS AND USES THEREOF<br/>[FR] CHÉLATEURS DE FER NEUROPROTECTEURS ET NEURORESTAURATEURS ET INHIBITEURS DE LA MONOAMINE-OXYDASE ET LEURS UTILISATIONS
  申请人：VARINEL INC

  公开号：WO2012020389A1

  公开（公告）日：2012-02-16

  8-Hydroxy-quinoline derivatives and 8-ethers, 8-esters, 8-carbonates, 8-acyloxymethyl, 8- phosphates, (phosphoryloxy)methyl, and 8-carbamates derivatives thereof are described that exhibit iron chelation, neuroprotective, neurorestorative, apoptotic and/or selective MAO-AB inhibitory activities.

  描述了表现出铁螯合、神经保护、神经恢复、凋亡和/或选择性MAO-AB抑制活性的8-羟基喹啉衍生物和8-醚、8-酯、8-碳酸酯、8-酰氧甲基、8-磷酸酯、(磷酸酯氧)甲基和8-氨基甲酸酯衍生物。
• 8-hydroxy-7-substituted quinolines as anti-viral agents
  申请人：Pharmacia & Upjohn Company

  公开号：US06211376B1

  公开（公告）日：2001-04-03

  The present invention provides for 8-hydroxy-7-substituted quinoline compounds such as formula III These compounds are useful as anti-viral agents. Specifically, these compounds have anti-viral activity against the herpes virus, cytomegalovirus (CMV). Many of these compounds are also active against other herpes viruses, such as the varicella zoster virus, the Epstein-Barr virus, the herpes simplex virus and the human herpes virus type 8 (HHV-8).

  本发明提供了8-羟基-7-取代喹啉类化合物，如公式III所示。这些化合物可用作抗病毒剂。具体而言，这些化合物对疱疹病毒、巨细胞病毒（CMV）具有抗病毒活性。许多这些化合物也对其他疱疹病毒具有活性，如水痘带状疱疹病毒、爱泼斯坦-巴尔病毒、单纯疱疹病毒和人类疱疹病毒8型（HHV-8）。
• Pyridine hydrochloride: a new reagent for the synthesis of o-chloro hydroxy derivatives in pyridine and quinoline series
  作者：Florence Mongin、Olivier Mongin、François Trécourt、Alain Godard、Guy Quéguiner

  DOI：10.1016/s0040-4039(96)01449-9

  日期：1996.9

  Pyridine hydrochloride has been widely used in the cleavage of ethers. It is shown herein that this reagent is also efficient for the synthesis of chloro compounds starting from the corresponding bromo derivatives in π-deficient series such as pyridine and quinoline. Thus, for example, 7-bromo-8-hydroxyquinoline was almost quantitatively converted into 7-chloro-8-hydroxyquinoline. The scope of the

  吡啶盐酸盐已广泛用于醚的裂解中。在此表明，该试剂对于从π-缺乏系列的相应溴衍生物例如吡啶和喹啉开始的氯化合物的合成也是有效的。因此，例如，7-溴-8-羟基喹啉几乎定量地转化为7-氯-8-羟基喹啉。已经研究了反应范围。
• A SAR Study: Evaluation of Bromo Derivatives of 8-Substituted Quinolines as Novel Anticancer Agents
  作者：Salih Okten、Osman Cakmak、Saban Tekin、Tugba Kul Koprulu

  DOI：10.2174/1570180814666170504150050

  日期：2017.10.31

  for their anticancer effects on various cell lines. 5,7-Dibromo- 5, 7-bromo- 6, 7-cyano- 11 and 5,7-dicyano-12 8-hydroxyquinolines were shown to have strong antiproliferative activity against various tumor cell lines, including C6 (rat brain tumor), HeLa (human cervix carcinoma), and HT29 (human colon carcinoma) with IC50 values ranged from 6.7 to 25.6 µg/mL. Methods: A structure activity relationship

  背景：在体外评估了溴化的8-羟基，8-甲氧基，8-氨基喹啉5、6、8、9和新型氰基8-羟基喹啉11、12对各种细胞系的抗癌作用。显示5,7-二溴-5、7-溴-6、7-氰基-11和5,7-二氰基-12 8-羟基喹啉对包括C6（大鼠脑肿瘤）在内的多种肿瘤细胞系具有很强的抗增殖活性。 ，HeLa（人宫颈癌）和HT29（人结肠癌）的IC50值范围为6.7至25.6 µg / mL。 方法：建立结构活性关系（SAR），以喹啉核心的C-8位含羟基的基团产生更多的抗癌潜力。 结果：乳酸脱氢酶（LDH）细胞毒性，DNA阶梯化和抑制分析结果表明5、6、11和12具有高细胞毒性作用和潜在的细胞凋亡潜力。 结论：此外，5和12对Topoisomerase I酶抑制了超螺旋吡co DNA的松弛。结果，5、6、11和12可能具有有前途的抗癌药潜力，而5和12可能是新型拓扑异构酶抑制剂。
• Bromine-Lithium exchange on bromo-8-hydroxyquinolines via formation of their sodium salts
  作者：Florence Mongin、Jean-Marie Fourquez、Stéphanie Rault、Vincent Levacher、Alain Godard、François Trécourt、Guy Quéguiner

  DOI：10.1016/0040-4039(95)01776-e

  日期：1995.11

  A short and versatile method is reported for the preparation of 8-hydroxyquinoline derivatives by reaction of n-butyllithium with 5,7-dibromo-8-hydroxyquinoline 2 and 7-bromo-8-hydroxyqumoline 1 as their sodium salts. Thus, bromine-lithium exchange reaction on compound 2, highly regioselective, gave after addition of various electrophiles, 5-substituted 7-bromo-8-hydroxyquinolines 4a-j in moderate

  据报道，通过使正丁基锂与作为钠盐的5,7-二溴-8-羟基喹啉2和7-溴-8-羟基喹啉1反应，制备8-羟基喹啉衍生物的一种短而通用的方法。因此，在区域2上具有高区域选择性的溴-锂交换反应在添加各种亲电试剂后以中等至良好的产率产生了5-取代的7-溴-8-羟基喹啉4a-j。相同的方法也适用于产生7-取代的8-羟基喹啉3a-b的7-溴-8-羟基喹啉1。