8-氯异喹啉 | 34784-07-1

• 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-氯异喹啉
• 英文名称: 8-chloroisoquinoline
• 英文别名: 8-Chlor-isochinolin
• CAS: 34784-07-1
• 化学式: C₉H₆ClN
• mdl: MFCD07644622
• 分子量: 163.606
• InChiKey: OXAMVYYZTULFIB-UHFFFAOYSA-N

物化性质

• 熔点：
  55.5-56.5 °C
• 沸点：
  289.5±13.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

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

• 危险品标志：
  Xi
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 8-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: 8-Chloroisoquinoline
CAS number: 34784-07-1

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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: 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

制备方法与用途

应用

8-氯异喹啉可用作有机合成中间体和医药中间体，主要应用于实验室研发和化工生产过程。作为一种取代异喹啉化合物，它在这些领域发挥着重要作用。

反应信息

• 作为反应物：
  描述：

  8-氯异喹啉 在 potassium tert-butylate 、 N,N-二甲基甲酰胺 作用下， 反应 24.0h， 以75%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：

  N-[(2-chlorophenyl)methylene]-2,2-dimethoxyethanamine 在 硫酸 作用下， 反应 0.5h， 生成 8-氯异喹啉
  参考文献：
  名称：

  Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.

  DOI：

  10.1021/jm00179a007

文献信息

• Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine
  作者：Tibor Soós、Dániel Horváth、Frigyes Domonyi、Roberta Palkó、Andrea Lomoschitz

  DOI：10.1055/s-0037-1609153

  日期：2018.6

  functionalization of the carbocyclic core of the isoquinoline. This regioexhaustive approach employs electrophilic halogenation as a toolbox methodology and delivers highly decorated intermediates that can be further elaborated toward medicinally relevant building blocks or natural products. A general and versatile strategy has been developed for the functionalization of the carbocyclic core of the isoquinoline. This

  摘要 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。
• Copper-Mediated Oxidative Functionalization of C(sp³)–H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones
  作者：Dingyi Wang、Rongxing Zhang、Ruihong Deng、Sen Lin、Shengmei Guo、Zhaohua Yan

  DOI：10.1021/acs.joc.6b02145

  日期：2016.11.18

  functionalization of C(sp3)–H bonds with isoquinolines via a radical process without ligands was achieved. The present system exhibits a novel pathway for the preparation of N-alkyl (benzyl) isoquinolin-1(2H)-ones in moderate to high yields. In addition, this procedure provides a simple method to afford 5-oxaprotoberberinones and their derivatives in two steps.

  通过没有配体的自由基过程实现了铜介导的C（sp 3）–H键与异喹啉的氧化功能化。本系统展示了以中等至高收率制备N-烷基（苄基）异喹啉-1（2H）-的新颖途径。此外，该程序提供了一种简单的方法，可分两步获得5-氧杂小ber碱和它们的衍生物。
• Photoredox-Catalyzed Decarboxylative C–H Acylation of Heteroarenes
  作者：Chao Yang、Wujiong Xia、Wei Jia、Yong Jian、Binbin Huang

  DOI：10.1055/s-0037-1609911

  日期：2018.9

  A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly realize the acylation of various heterocyclic compounds.

  据报道，通过光氧化还原催化，杂环与廉价羧酸的温和、环境友好和区域选择性酰化。该策略具有良好的官能团耐受性和底物范围，可以快速实现各种杂环化合物的酰化。
• [EN] THIAZOLES AS MODULATORS OF RORyt<br/>[FR] THIAZOLES UTILISÉS COMME MODULATEURS DE RORYT
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2016069976A1

  公开（公告）日：2016-05-06

  The present invention comprises compounds of Formula I. Formula I wherein: R1, R2, R3, R4, R5, R7, R8, and (A) are defined in the specification. The invention also comprises a compound of Formula I for use in a method of treating or ameliorating a syndrome, disorder or disease, wherein said syndrome, disorder or disease is rheumatoid arthritis or psoriasis. The invention also comprises a compound for use in a method of modulating RORγt activity in a mammal by administration of a therapeutically effective amount of at least one compound of claim 1.

  本发明包括公式I的化合物。公式I中：R1、R2、R3、R4、R5、R7、R8和(A)在说明书中定义。该发明还包括用于治疗或改善综合症、紊乱或疾病的公式I化合物，其中所述综合症、紊乱或疾病为类风湿性关节炎或银屑病。该发明还包括用于通过管理治疗有效量的至少一个权利要求1的化合物来调节哺乳动物中RORγt活性的化合物。
• Iodination/Amidation of the <i>N</i>-Alkyl (Iso)quinolinium Salts
  作者：Juan Tang、Xue Chen、Chao-qun Zhao、Wen-jing Li、Shun Li、Xue-li Zheng、Mao-lin Yuan、Hai-yan Fu、Rui-xiang Li、Hua Chen

  DOI：10.1021/acs.joc.0c02321

  日期：2021.1.1

  NaIO4-mediated sequential iodination/amidation reaction of N-alkyl quinolinium iodide salts has been first developed. This cascade process provides an efficient way to rapidly synthesize 3-iodo-N-alkyl quinolinones with high regioselectivity and good functional group tolerance. This protocol was also amenable to the isoquinolinium salts, thus providing a complementary method for preparing the 4-iodo-N-alkyl

  所述的NaIO 4介导的顺序碘化/酰胺化的反应ñ -烷基喹啉鎓碘化物盐已被首先开发。该级联过程提供了快速合成具有高区域选择性和良好的官能团耐受性的3-碘-N-烷基喹啉酮的有效方法。该方案也适用于异喹啉鎓盐，因此提供了制备4-碘-N-烷基异喹啉酮的补充方法。

表征谱图