8-羟基异喹啉 | 3482-14-2

• 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 - 异喹啉及其衍生物
• 中文名称: 8-羟基异喹啉
• 英文名称: isoquinolin-8-ol
• 英文别名: 8-hydroxyisoquinoline；8-Hydroxy-isochinolin；isoquinoline-8-ol；MFCD 00661583；Isoquinolin-8-ol
• CAS: 3482-14-2
• 化学式: C₉H₇NO
• 分子量: 145.161
• InChiKey: ZIXWTPREILQLAC-UHFFFAOYSA-N

物化性质

• 熔点：
  213 °C
• 沸点：
  332.1±15.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 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：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn,Xi
• 危险类别码：
  R22
• 海关编码：
  2933499090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，密封于干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 8-Hydroxyisoquinoline
Synonyms: Isoquinolin-8-ol

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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: 8-Hydroxyisoquinoline
CAS number: 3482-14-2

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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, refrigerated.
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: C9H7NO
Molecular weight: 145.2

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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.

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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

合成方法如下：

2-甲氧基苯甲醛和2,2-二甲氧基乙胺在苯中发生醛胺缩合反应，再与氯甲酸乙酯和亚磷酸三甲酯反应生成8-甲氧基异喹啉-4(3H)-酮中间体。此中间体在二氯甲烷中回流条件下与四氯化钛作用脱水生成8-甲氧基异喹啉。最后，该中间体在低温下于二氯甲烷中与三溴化硼反应进行脱甲基生成8-羟基异喹啉。

反应信息

• 作为反应物：
  描述：

  8-羟基异喹啉 在 ammonium hydroxide 、 二氧化硫 作用下， 生成 8-氨基异喹啉
  参考文献：
  名称：

  7-(γ-Diethylaminopropylamino)-isoquinoline¹

  摘要：

  DOI：

  10.1021/ja01200a030
• 作为产物：
  描述：

  8-氯异喹啉 在 copper acetylacetonate 、 lithium hydroxide monohydrate 、 1,3-bis(4-hydroxy-2,6-dimethylphenyl)urea 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 24.0h， 以72%的产率得到8-羟基异喹啉
  参考文献：
  名称：

  8-羟基异喹啉的合成方法

  摘要：

  8‑羟基异喹啉的合成方法，属于异喹啉类化合物的合成方法领域。包括以下步骤：在二甲基亚砜和水的混合溶液中加入8‑氯异喹啉、乙酰丙酮铜、一水合氢氧化锂和配体1,3‑双(4‑羟基‑2,6‑二甲基苯基)脲；在氮气保护下，将所配反应液边加热边搅拌直至反应完成；待搅拌后的反应液冷却后，用HCl酸化至pH＝5；将混合液用乙酸乙酯萃取，萃取后的有机相用饱和食盐水洗涤，经过无水硫酸钠干燥后旋干，粗产品经柱层析分离后制得8‑羟基异喹啉。本发明提供了一种以8‑氯异喹啉为原料，合成路线简洁，工艺选择合理，原料简单易得，操作和后处理方便，总收率高达72％，易于放大，可进行大规模生产的8‑羟基异喹啉的合成方法。

  公开号：

  CN106966977A
• 作为试剂：
  描述：

  间硝基三氟甲苯 在 iron(III) chloride 、 8-羟基异喹啉 、 copper(l) iodide 、 hydrazine hydrate 、 硫酸 、 溴 、 potassium carbonate 、 甲烷 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 3-(4-甲基-1H-咪唑-1-基)-5-(三氟甲基)苯胺
  参考文献：
  名称：

  Method for preparing nilotinib intermediate

  摘要：

  本发明公开了一种制备尼洛替尼中间体3-(4-甲基-1H-咪唑-1-基)-5-三氟甲基苯胺(I)的方法。该方法包括以下步骤：以三氟甲基甲苯为原料，通过硝化、溴化、缩合和还原依次制备尼洛替尼中间体(I)。与现有技术相比，该制备方法具有以下优点：产率相对较高，原材料易获得，工艺简洁，副反应少，适合工业生产，促进了大宗药物的经济技术发展。

  公开号：

  US20160311777A1

文献信息

• Tyrosine Kinase Inhibitor And Uses Thereof
  申请人：Xuanzhu Pharma Co., Ltd.

  公开号：US20170112833A1

  公开（公告）日：2017-04-27

  Disclosed is a compound of Formula (I) or a pharmaceutically acceptable salt, ester, or solvate thereof, or their stereoisomers, which can be used as tyrosine kinase inhibitor. Also disclosed is a method for preparing the compound, a pharmaceutical composition and a kit comprising the compound, and uses of the compound. The compound can be used as tyrosine kinase inhibitor, or can be used to reduce or inhibit activity of EGFR or mutant thereof, such as EGFR mutant comprising T790M mutation, in a cell, or to treat and/or prevent a disease associated with overactivity of EGFR, such as cancer.

  公开了一种公式(I)的化合物或其药物可接受的盐、酯或溶剂，或它们的立体异构体，可用作酪氨酸激酶抑制剂。还公开了制备该化合物的方法、包含该化合物的药物组合物和套件，以及该化合物的用途。该化合物可用作酪氨酸激酶抑制剂，或可用于减少或抑制细胞中EGFR或其突变体的活性，例如包含T790M突变的EGFR突变体，或用于治疗和/或预防与EGFR过度活动相关的疾病，如癌症。
• [EN] PYRIDAZINONE DERIVATIVES AND USE THEREOF AS P2X7 RECEPTOR INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDAZINONE ET LEUR UTILISATION COMME INHIBITEURS DU RÉCEPTEUR P2X7
  申请人：NISSAN CHEMICAL IND LTD

  公开号：WO2009057827A1

  公开（公告）日：2009-05-07

  Novel pyridazinone compounds of formula (I), which inhibit the purinergic P2X7 receptor and are useful for prevention, therapy and improvement of inflammatory and immunological diseases.

  翻译结果为：新型的哒嗪酮化合物，其化学公式为(I)，能够抑制嘌呤能P2X7受体，并对预防、治疗和改善炎症性和免疫性疾病有益。
• 정공 주입 특성을 구비한 유기 화합물 및 그를 이용한 유기 발광 소자와 디스플레이 장치
  申请人：LG Display Co.,Ltd. 엘지디스플레이 주식회사(119981018655) Corp. No ▼ 110111-0393134

  公开号：KR20160083249A

  公开（公告）日：2016-07-12

  본 발명은, 하기 화학식 1: 화학식 1 로 표시되는 정공 주입 특성을 구비한 유기 화합물 및 그를 이용한 유기 발광 소자와 디스플레이 장치에 관한 것으로서, 본 발명에 따르면 유기 발광 소자의 구동 전압을 낮출 수 있다.

  本发明涉及如下化学式1所示的具有正空注入特性的有机化合物及其用于的有机发光器件和显示装置，根据本发明，可以降低有机发光器件的驱动电压。
• 作为神经保护剂的药用化合物
  申请人：江苏先声药业有限公司

  公开号：CN104045552B

  公开（公告）日：2019-06-11

  本发明公开了一类作为神经保护剂的药用化合物，其为神经元型一氧化氮合酶‑突触后密度蛋白‑95（nNOS‑PSD95）的解耦联剂，其为具有通式（Ⅰ）苯环衍生物或其药学上可接受的盐。本申请进一步公开了该类化合物的制备方法以及其用于预防和治疗受神经元损伤影响引起的疾病的用途。
• [EN] 7- OR 8-HYDROXY-ISOQUINOLINE AND 7- OR 8-HYDROXY-QUINOLINE DERIVATIVES AS ALPHA-1 -ANTITRYPSIN MODULATORS FOR TREATING ALPHA-1 -ANTITRYPSIN DEFICIENCY (AATD)<br/>[FR] DÉRIVÉS DE 7-OU 8-HYDROXY-ISOQUINOLÉINE ET DE 7-OU 8-HYDROXY-QUINOLÉINE EN TANT QUE MODULATEURS D'ALPHA-1-ANTITRYPSINE POUR TRAITER UNE DÉFICIENCE EN ALPHA-1-ANTITRYPSINE (AATD)
  申请人：VERTEX PHARMA

  公开号：WO2021203028A1

  公开（公告）日：2021-10-07

  7- or 8-hydroxy-isoquinoline and 7- or 8-hydroxy-quinoline derivatives as alpha-l-antitrypsin modulators for treating alpha-l-antitrypsin deficiency (AATD).

  7-或8-羟基异喹啉和7-或8-羟基喹啉衍生物作为治疗α-1-抗胰蛋白酶缺乏症（AATD）的α-1-抗胰蛋白酶调节剂。

表征谱图