6-溴-4-羟基喹啉 | 145369-94-4

• 物质功能分类: 医药中间体 - 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-4-羟基喹啉
• 中文别名: 4-羟基-6-溴喹啉；6-溴喹啉-4-醇
• 英文名称: 6-bromoquinolin-4-ol
• 英文别名: 6-bromo-4-hydroxyquinoline；4-hydroxy-6-bromoquinoline；6-bromo-1H-quinolin-4-one
• CAS: 145369-94-4
• 化学式: C₉H₆BrNO
• mdl: MFCD00272435
• 分子量: 224.057
• InChiKey: XKLBNOHKHRAXKK-UHFFFAOYSA-N

物化性质

• 熔点：
  283°C(lit.)
• 沸点：
  370.7±22.0 °C(Predicted)
• 密度：
  1.705±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38,R22
• 海关编码：
  29334900
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
6-Bromoquinolin-4-ol
Product Name:
Synonyms: 6-Bromo-4-hydroxyquinoline

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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-Bromoquinolin-4-ol
Ingredient name:
CAS number: 145369-94-4

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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: C9H6BrNO
Molecular weight: 224.1

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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 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

制备将4-溴代苯胺（5.0 g，29.6 mmol）和丙二酸二乙酯-（乙氧基）乙烯（5.8 ml，29.6 mmol）的混合物溶解在苯醚（50 ml）中，回流过夜。冷却后产物，加入石油醚（200 ml），过滤沉淀物并用石油醚洗涤，然后真空干燥，得到灰色固体标题化合物（5.3 g，产率65%）。其结构通过1H NMR（400 MHz，DMSO-d6）确认，谱图显示δ 10.66 (d, J=3.89 Hz, 1 H)，8.36 (d, J=3.64 Hz, 1 H)，7.56 (d, J=0.84 Hz, 1 H)。

应用6-溴-4-羟基喹啉作为冶金、染料、聚合物以及农用化学品工业的重要中间体，广泛应用于制造各种功能性产品。此外，它还可以用作消毒剂、防腐剂及溶剂，在多个领域展现出其独特的价值。

反应信息

• 作为反应物：
  描述：

  6-溴-4-羟基喹啉 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 、 一水合肼 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 丙酮 为溶剂， 反应 26.0h， 生成 2-(3-(thiophen-2-yl)quinolin-4-yloxy)acetohydrazide
  参考文献：
  名称：

  具有不同杂原子的生物活性部分的组合：铃木交叉偶联反应的应用

  摘要：

  已经通过 Suzuki 交叉偶联反应合成了两个系列的噻吩/苯并噻吩连接的喹啉基恶二唑，它们与取代的 N-苯并噻唑基乙酰胺缩合。6-溴取代喹啉的酯衍生物通过 Suzuki 交叉偶联反应与市售（苯并）噻吩-2-基硼酸在优化温度下在 1,2-二甲氧基乙烷和水中在碳酸钾和碳酸钾存在下反应。四氯化钯。然后使用 99% 的水合肼将所得衍生物肼化，然后在乙醇 KOH 中使用二硫化碳环化以提供相应的恶二唑，然后将其与各种取代的 2-氯-N-苯并噻唑基乙酰胺缩合以产生最终的支架，其中涉及四种杂环的独特组合，以检查它们对两种革兰氏阳性菌（金黄色葡萄球菌和蜡状芽孢杆菌）、三种革兰氏阳性菌的抗菌活性-阴性细菌（大肠杆菌、铜绿假单胞菌和肺炎克雷伯菌）和两种真菌（黑曲霉和白色念珠菌）。生物筛选数据的调查显示，与标准品相比，大多数测试的化合物对大多数微生物表现出优异的活性（最低抑制浓度；6.25-50 µg/mL），因此它们值得更多考虑作为未来的抗菌剂

  DOI：

  10.1002/hc.21027
• 作为产物：
  描述：

  5-[(4-溴苯基氨基)亚甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮 在 二苯醚 作用下， 反应 0.25h， 生成 6-溴-4-羟基喹啉
  参考文献：
  名称：

  作为 PI3K/mTOR 双抑制剂的新型苯磺酰脲衍生物的设计、合成和生物学评价

  摘要：

  设计、合成了五个系列的新型苯磺酰脲衍生物，19a-d、20a-d、21a-d、22a-d 和 23a-d，带有 4-苯基氨基喹啉支架，并且它们对四种癌细胞系（HepG-2、 A549、PC-3 和 MCF-7) 进行了评估。大多数化合物对癌细胞系显示出中等的细胞毒性活性。构效关系（SAR）和药理学结果表明，4-氨基喹啉支架和苯磺酰脲支架的引入有利于抗肿瘤活性。此外，4-苯胺基部分的对甲氧基取代和苯磺酰脲的对卤素取代对不同系列的化合物有不同的影响。此外，

  DOI：

  10.3390/molecules23071553

文献信息

• A visible-light-irradiated electron donor-acceptor complex-promoted radical reaction system for the C H perfluoroalkylation of quinolin-4-ols
  作者：Yunze Li、Min Rao、Zhenwei Fan、Baoyi Nian、Yaofeng Yuan、Jiajia Cheng

  DOI：10.1016/j.tetlet.2019.151046

  日期：2019.9

  An efficient method for visible-light-induced perfluoroalkylaion of quinolin-4-ol has been reported. In the presence of t-BuONa and perfluoroalkyl iodide, quinolin-4-ol underwent CH perfluoroalkylation under the irradiation of green light. Mechanistic studies demonstrated that visible-light promoted intermolecular charge transfer within the transient electron donor-acceptor complex in the absence of

  已经报道了可见光诱导的喹啉-4-醇全氟烷基阴离子的有效方法。在t- BuONa和全氟烷基碘的存在下，喹啉-4-醇在绿光照射下经历了C H全氟烷基化。机理研究表明，在没有任何光催化剂的情况下，可见光促进了瞬态电子供体-受体复合物中分子间的电荷转移。
• [EN] COMBINATION OF KINASE INHIBITORS AND USES THEREOF<br/>[FR] COMBINAISON D'INHIBITEURS DE KINASE ET SES UTILISATIONS
  申请人：INTELLIKINE LLC

  公开号：WO2014151147A1

  公开（公告）日：2014-09-25

  The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase a and/or mTOR in a subject. In yet another aspect, a method of inhibiting phosphorylation of both Akt (S473) and Akt (T308) in a cell is set forth. The present invention also provides a pharmaceutical kit effective for treating a disease condition associated with PI3 -kinase α and/or mTOR in a subject.

  本发明提供了一种治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的方法。另一方面，该发明提供了一种治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的方法。在另一个方面，提出了一种抑制细胞内Akt（S473）和Akt（T308）磷酸化的方法。本发明还提供了一种有效治疗与受体内PI3-激酶α和/或mTOR相关的疾病状况的药物套装。
• COMBINATION OF KINASE INHIBITORS AND USES THEREOF
  申请人：INTELLIKINE, LLC

  公开号：US20150030588A1

  公开（公告）日：2015-01-29

  The present invention provides for a method for treating a disease condition associated with PI3-kinase a and/or a receptor tyrosine kinase (RTK) in a subject. In another aspect, the invention provides for a method for treating a disease condition associated with PI3-kinase α and/or an RTK in a subject. In yet another aspect, a method of inhibiting phosphorylation of Akt (S473) in a cell is set forth.

  本发明提供了一种治疗与PI3-激酶a和/或受体酪氨酸激酶（RTK）有关的疾病状况的方法。另一方面，该发明提供了一种治疗与PI3-激酶α和/或受体酪氨酸激酶（RTK）有关的疾病状况的方法。另一方面，提出了一种抑制细胞中Akt（S473）磷酸化的方法。
• Condensed derivatives of imidazole useful as pharmaceuticals
  申请人：LABORATOIRE BIODIM

  公开号：EP2913330A1

  公开（公告）日：2015-09-02

  The invention relates to the compounds (I) and their acids and bases salts: wherein: the dotted line indicates a double bond; X is N or C-R1 and Y is N or C-R2, X and Y not being simultaneously N; A is selected from the group consisting of phenyl, naphthyl and (5-11) membered monocyclic or bicyclic unsaturated cycle or heterocycle possibly substituted as defined in the application, and A can also comprise either a further (4-7) membered heterocycle, said heterocycle being a monocycle, fused, saturated or unsaturated, the polycyclic system then comprising up to 14 members and up to 5 heteroatoms selected from N, O and S; B is Hydrogen or a substituent as defined in the application, or B is a (4-10) membered mono or bicyclic saturated or unsaturated heterocycle containing 1-3 heteroatoms selected from N, O and S, and possibly substituted as defined in the application; B not being Hydrogen when X is N and Y is C-R2; R1 is Hydrogen or a substituent as defined in the application; B and R1 cannot be simultaneously Hydrogen; R2 is Hydrogen or Halogen; their preparation, their use in the antibacterial prevention and therapy, alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity, and pharmaceutical compositions and associations containing them.

  该发明涉及化合物（I）及其酸盐和碱盐： 其中： 虚线表示双键； X为N或C-R1，Y为N或C-R2，X和Y不同时为N； A选自苯基、萘基和（5-11）成员单环或双环不饱和环或杂环，可能按申请中定义进行取代， A还可以包括另一个（4-7）成员杂环，该杂环为单环、融合、饱和或不饱和，多环系统则包括最多14个成员和最多5个N、O和S中选择的杂原子； B为氢或按申请中定义的取代基，或 B为含有1-3个N、O和S中选择的杂原子的（4-10）成员单环或双环饱和或不饱和杂环，并可能按申请中定义进行取代； 当X为N且Y为C-R2时，B不是氢； R1为氢或按申请中定义的取代基； B和R1不能同时为氢； R2为氢或卤素； 它们的制备，它们在抗菌预防和治疗中的用途，单独或与抗菌药物、抗毒力剂或增强宿主先天免疫力的药物联合使用，以及含有它们的药物组合物和联合物。
• [EN] PAPD5 INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS DE PAPD5 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CHILDRENS MEDICAL CENTER

  公开号：WO2020219729A1

  公开（公告）日：2020-10-29

  The present application provides compounds that are PAPD5 inhibitors and are useful in treating a variety of conditions such as cancer, telomere diseases, and aging-related and other degenerative disorders.

  本申请提供了一些PAPD5抑制剂化合物，可用于治疗各种疾病，如癌症、端粒疾病以及与衰老和其他退行性疾病相关的情况。