4-氯异喹啉 | 1532-91-8

• 物质功能分类: 医药中间体 - 异喹啉类化合物
• 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: 4-氯异喹啉
• 中文别名: 4-氯异喹林
• 英文名称: 4-chloroisoquinoline
• 英文别名: 4-Chlor-isochinolin
• CAS: 1532-91-8
• 化学式: C₉H₆ClN
• mdl: MFCD00234490
• 分子量: 163.606
• InChiKey: LBEQEEIDWHKVAR-UHFFFAOYSA-N

物化性质

• 熔点：
  27.5-29.5 °C
• 沸点：
  130-132 °C(Press: 9 Torr)
• 密度：
  1.225 g/cm3(Temp: 21 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  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：
  P305+P351+P338
• 危险性描述：
  H302,H319
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Chloroisoquinoline
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: 4-Chloroisoquinoline
CAS number: 1532-91-8

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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: C9H6ClN
Molecular weight: 163.6

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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.

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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：

  4-氯异喹啉 在 potassium tert-butylate 、 N,N-二甲基甲酰胺 作用下， 反应 24.0h， 以91%的产率得到异喹啉
  参考文献：
  名称：

  可见光诱导的碱促进的芳基氟化物，氯化物，溴化物和碘化物的无过渡金属脱卤化作用

  摘要：

  我们报告了简单有效的芳基卤化物的可见光诱导的无过渡金属氢化。可见光和碱的组合系统用于引发所需的自由基介导的氢化反应。在温和条件下，可以将多种芳基氟化物，氯化物，溴化物和碘化物还原成相应的（杂）芳烃。可以容忍各种官能团和其他杂环化合物。

  DOI：

  10.1021/acs.orglett.0c00827
• 作为产物：
  描述：

  异喹啉 在 碘苯二乙酸 、 氯甲酸乙酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以92%的产率得到4-氯异喹啉
  参考文献：
  名称：

  （杂）芳烃通过瞬态，非对称碘代烷的位点选择性CH功能化。

  摘要：

  已经开发了一种将芳烃和杂芳烃进行C-H官能化的策略，以允许位点选择性结合各种阴离子，包括Cl，Br，OMs，OTs和OTf。通过结合阴离子和稳定的PhI（OAc）2原位生成反应性，不对称碘化物，可以实现此方法。该机制的实用性通过与药用相关的芳烃的对位选择性氯化以及杂芳烃的位点选择性C–H氯化反应得以证明。光谱，计算和竞争实验描述了这些瞬态，不对称碘的独特性质，反应性和选择性。

  DOI：

  10.1016/j.chempr.2018.11.007

文献信息

• Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions
  作者：Shanghua Xia、Lu Gan、Kailiang Wang、Zheng Li、Dawei Ma

  DOI：10.1021/jacs.6b08114

  日期：2016.10.19

  powerful catalytic system for hydroxylation of (hetero)aryl halides. A wide range of (hetero)aryl chlorides bearing either electron-donating or -withdrawing groups proceeded well at 130 °C, delivering the corresponding phenols and hydroxylated heteroarenes in good to excellent yields. When more reactive (hetero)aryl bromides and iodides were employed, the hydroxylation reactions completed at relatively

  Cu(acac)2 和 N,N'-双(4-羟基-2,6-二甲基苯基)草酰胺 (BHMPO) 的组合为（杂）芳基卤化物的羟基化提供了强大的催化系统。各种带有给电子或吸电子基团的（杂）芳基氯化物在 130 °C 下均能很好地进行，以良好到极好的产率提供相应的酚类和羟基化杂芳烃。当使用反应性更强的（杂）芳基溴化物和碘化物时，羟基化反应在相对较低的温度（分别为 80 和 60 °C）下在低催化负载（0.5 mol% Cu）下完成。
• 5-Substituted isoquinoline derivatives
  申请人：Yamada Rintaro

  公开号：US20050020623A1

  公开（公告）日：2005-01-27

  A compound represented by the following formula (1) or a salt thereof: wherein R 1 represents hydrogen atom, a halogen atom and the like; R 2 represents hydrogen atom, a halogen atom, a C 1-6 alkyl group and the like; and R 3 represents —O—X—C(A 1 )(A 11 )—C(A 2 )(A 2l )—N(A 3l )(A 3 )(X represents propylene group etc., A 11 and A 21 represent hydrogen atom, or a C 1-6 alkyl group, A 31 represents a C 1-6 alkyl group substituted with hydroxyl group, or hydrogen atom, and A 1 , A 2 , and A 3 represent hydrogen atom, a C 1-6 alkyl group and the like) and the like, which has an inhibitory activity on the phosphorylation of myosin regulatory light chain, and is useful for treatment of diseases relating to contraction of various cells and the like.

  由以下公式（1）表示的化合物或其盐： 其中R1代表氢原子、卤素原子等；R2代表氢原子、卤素原子、C1-6烷基团等；R3代表—O—X—C(A1)(A11)—C(A2)(A21)—N(A31)(A3)（X代表丙烯基等，A11和A21代表氢原子或C1-6烷基团，A31代表被羟基取代的C1-6烷基团或氢原子，A1、A2和A3代表氢原子、C1-6烷基团等）等，该化合物对肌球蛋白调节轻链的磷酸化具有抑制作用，并且对涉及各种细胞收缩等的疾病的治疗有益。
• Direct C–H aminocarbonylation of <i>N</i>-heteroarenes with isocyanides under transition metal-free conditions
  作者：Zhong Zhou、Huihui Ji、Qing Li、Qian Zhang、Dong Li

  DOI：10.1039/d1ob00245g

  日期：——

  mediated by an inorganic persulfate salt under transition metal-free conditions. Mechanistic studies suggested a radical pathway for this reaction without the participation of H2O and O2. This method also showed merits of substrate availability, easy operation and atom economy. It provided an efficient route for straightforward synthesis of N-heteroaryl amides.

  开发了通过N-杂芳烃与异氰化物的直接 C-H 氨基羰基化合成 AC-C 键形成酰胺。该反应在无过渡金属条件下由无机过硫酸盐介导。机理研究提出了该反应的根本途径，无需 H 2 O 和 O 2的参与。该方法还显示出底物可用性、操作简便和原子经济性等优点。它为直接合成N-杂芳基酰胺提供了一条有效的途径。
• 一种异喹啉-1-甲酰胺类化合物的制备方法
  申请人：湖北工业大学

  公开号：CN113072496A

  公开（公告）日：2021-07-06

  本发明涉及一种异喹啉‑1‑甲酰胺类化合物的制备方法，将氧化剂、反应物一、反应物二和溶剂在反应器中混合，进行酰胺化反应，反应完成后分离纯化，得到异喹啉‑1‑甲酰胺类化合物；其中氧化剂为过硫酸盐；反应物一为异喹啉类化合物；反应物二任选自叔丁基异氰、苯基异氰、环己基异氰。本发明反应条件温和、选择性高、产率较高及对环境友好。经检测合成的异喹啉‑1‑甲酰胺类化合物具有一定的生物活性，可以应用到药物合成、农药合成以及涂料染料合成等领域。
• Ethynylation of Isoquinoline and Quinoline Derivatives with Calcium Carbide
  作者：Alireza Samzadeh-Kermani

  DOI：10.1055/s-0036-1590815

  日期：2017.10

  An operatically simple method for the ethynylation of isoquinolines and quinolines is described. The ionic adduct derived from an alkynoic ester and the N-heterocycle was attacked by calcium carbide to give the ethynylation product. The procedure uses tetrabutylammonium fluoride trihydrate as a catalyst in aqueous N , N -dimethylacetamide. Steric and electronic effects of various substituents on the

  描述了一种操作简单的异喹啉和喹啉乙炔化方法。衍生自炔酸酯和 N-杂环的离子加合物受到碳化钙的攻击，得到乙炔化产物。该程序使用四丁基氟化铵三水合物作为催化剂在 N, N-二甲基乙酰胺水溶液中。检查了各种取代基对反应结果的空间和电子效应。

表征谱图