喹啉-6-甲腈 | 23395-72-4

• 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: 喹啉-6-甲腈
• 英文名称: quinoline-6-carbonitrile
• 英文别名: 6-cyanoquinoline；6-Cyan-chinolin
• CAS: 23395-72-4
• 化学式: C₁₀H₆N₂
• 分子量: 154.171
• InChiKey: NIFLNJLWZZABMI-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134℃ (methanol )
• 沸点：
  323.7±15.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090
• 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：
  室温且干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Quinoline-6-carbonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H318: Causes serious eye damage
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: Quinoline-6-carbonitrile
CAS number: 23395-72-4

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
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
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C10H6N2
Molecular weight: 154.2

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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
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (Quinoline-6-carbonitrile)

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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：

  喹啉-6-甲腈 在 (1,1'-双(二苯基膦)二茂铁)二氯化镍 、 乙醇 、 双(三甲基硅烷基)氨基钾 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以43%的产率得到喹啉
  参考文献：
  名称：

  乙醇作为还原剂的镍催化腈还原氰化反应

  摘要：

  已经开发出镍催化的芳香腈的还原性脱氰，其中易得且丰富的乙醇用作氢化物供体。在该催化方案中，芳环上的各种官能团如烷氧基，氨基，亚氨基和酰胺是相容的。杂芳基，苄基和烯基腈也可耐受。机理研究表明，在该还原性脱氰反应中，乙醇通过消除β-氢化物有效地提供了氢化物。

  DOI：

  10.1039/d0cc07743g
• 作为产物：
  描述：

  6-羟甲基喹啉 在 ammonium hydroxide 作用下， 以 叔丁醇 为溶剂， 120.0 ℃ 、1.0 MPa 条件下， 反应 24.0h， 以94%的产率得到喹啉-6-甲腈
  参考文献：
  名称：

  用于有氧氧化合成（杂）芳香醛、酮、酯、酸、腈和酰胺的“通用”催化剂

  摘要：

  功能化（杂）芳族化合物是基础和应用科学中广泛使用的不可或缺的化学品。其中，尤其是芳香醛、酮、羧酸、酯、腈和酰胺是有价值的精细和大宗化学品，可用于化学、制药、农业化学和材料工业。对于它们的合成，醇的催化有氧氧化构成了一种绿色、可持续且具有成本效益的工艺，理想情况下应该利用活性和选择性的 3D 金属。在这里，我们报告了通过在碳上热解钴-哌嗪-酒石酸络合物作为最通用的氧化催化剂，制备包裹在 Co-纳米颗粒中的石墨层。这种独特的材料可以合成简单、功能化和结构多样的（杂）芳香醛、酮、

  DOI：

  10.1016/j.chempr.2021.12.001

文献信息

• 酰胺连续化制备腈的方法
  申请人：浙江大学衢州研究院

  公开号：CN112028726B

  公开（公告）日：2022-08-12

  本发明公开了一种酰胺连续化制备腈的方法，包括以下步骤：将铅盐与分子筛通过浸渍法制备成分子筛负载的铅催化剂，将分子筛负载的铅催化剂填充至固定床反应器内；将酰胺或酰胺溶液由固定床顶部送入固定床反应器内被催化脱水，所得的反应产物从固定床底部引出；所述反应产物经分离，得到酰胺所对应的腈的粗品。采用固定床连续化生产工艺，反应过程简单，生产效率高，产物后处理简单，易实现工业化生产。
• [EN] 2,3-DISUBSTITUTED 1 -ACYL-4-AMINO-1,2,3,4-TETRAHYDROQUINOLINE DERIVATIVES AND THEIR USE AS BROMODOMAIN INHIBITORS<br/>[FR] DÉRIVÉS 2,3-DISUBSTITUÉS DE 1-ACYL-4-AMINO-1,2,3,4-TÉTRAHYDROQUINOLÉINE ET LEUR UTILISATION COMME INHIBITEURS DE BROMODOMAINES
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2014140076A1

  公开（公告）日：2014-09-18

  The present invention relates to novel compounds of formula (I), wherein R1 is C1-4alkyl; R2 is C1-4alkyl, C3-7cycloalkyl, -CH2CF3, -CH2OCH3 or heterocyclyl; R3 is C1-4alkyl, -CH2F, -CH2OH or -CH2O(O)CH3; R4 when present is as defined in claim 1; R5 when present is H, halo, hydroxy or C1-6alkoxy; A is -NH-, -O-, -S-, -SO-, -SO2-, -N(C1-4alkyl)- or -NC(O)(CH3)-; V is phenyl, heteroaromatic or pyridone any of which may be optionally substituted by 1, 2 or 3 substituents; W is CH or N; X is C or N; Y is C or N; and Z is CH or N; subject to the proviso that no more than 2 of W, X, Y and Z are N, pharmaceutical compositions containing such compounds and to their use as bromodomain inhibitors.

  本发明涉及式(I)的新化合物，其中R1为C1-4烷基；R2为C1-4烷基、C3-7环烷基、-CH2CF3、- 或杂环烷基；R3为C1-4烷基、-CH2F、- H或-CH2O(O)CH3；R4存在时如权利要求1所定义；R5存在时为H、卤素、羟基或C1-6烷氧基；A为-NH-、-O-、-S-、-SO-、-SO2-、-N(C1-4烷基)-或-NC(O)( )-；V为苯基、杂芳基或吡啶酮，其中任何一个可以选择性地被1、2或3个取代基取代；W为CH或N；X为C或N；Y为C或N；Z为CH或N；但W、X、Y和Z中不超过2个为N，含有这种化合物的药物组合物以及它们作为溴结构域抑制剂的用途。
• Efficient cyanation of aryl bromides with K4[Fe(CN)6] catalyzed by a palladium-indolylphosphine complex
  作者：Pui Yee Yeung、Chun Pui Tsang、Fuk Yee Kwong

  DOI：10.1016/j.tetlet.2011.09.088

  日期：2011.12

  temperature reported so far for palladium-catalyzed cyanation of aryl bromides with K4[Fe(CN)6] source in general. Common functional groups, including keto, aldehyde, free amine, and heterocyclic substrates are compatible under this system. Interestingly, the phosphine ligands bearing –PCy2 moiety, which usually show excellent activity in aryl halide couplings, are found less effective than the corresponding

  这项研究描述了使用K 4 [Fe（CN）6 ]作为氰化物替代物的一般钯催化的芳基溴化物的氰化反应。该反应可以在温和的反应条件下（在50°C下）在没有任何表面活性剂添加剂的混合溶剂（水/ MeCN = 1：1）中成功进行，并以令人满意的良好收率得到所需的芳基腈。特别值得一提的是，对于钯催化的一般用K 4 [Fe（CN）6 ]源进行的芳基溴化物的钯催化氰化反应，该系统可实现迄今为止最温和的反应温度。常见的官能团，包括酮基，醛基，游离胺基和杂环底物，在此系统下均兼容。有趣的是，带有–PCy 2的膦配体发现通常在芳基卤化物偶联中表现出出色活性的碳原子部分比具有-PPh 2基团的相应配体的有效性低。
• A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Mesylates in Water or tBuOH/Water
  作者：Pui Yee Yeung、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/anie.201005121

  日期：2010.11.15

  Cool and compatible: Aryl mesylates and tosylates underwent palladium‐catalyzed cyanation under mild, aqueous conditions at 65–80 °C (see scheme). In many cases, water could be used as the reaction medium without a cosolvent, and a variety of substituents R, such as keto, aldehyde, ester, free amine, and nitrile groups, remained intact during the transformation. Cy=cyclohexyl, Ms=methanesulfonyl,

  凉爽且相容：芳基甲磺酸酯和甲苯磺酸酯在65-80°C的温和水溶液条件下经历了钯催化的氰化反应（请参见方案）。在许多情况下，可以将水用作没有助溶剂的反应介质，并且在转化过程中，各种取代基R（例如酮，醛，酯，游离胺和腈基）保持完整。Cy =环己基，Ms =甲磺酰基，Ts =对甲苯磺酰基。
• Nickel-Catalyzed Deoxycyanation of Activated Phenols via Cyanurate Intermediates with Zn(CN)₂: A Route to Aryl Nitriles
  作者：Majid M. Heravi、Farhad Panahi、Nasser Iranpoor

  DOI：10.1021/acs.orglett.8b00974

  日期：2018.5.4

  A novel, and efficient nickel-catalyzed deoxycyanation of phenolic compounds using relatively nontoxic Zn(CN)2 as the cyanide source was developed. The reaction of C–O bond activated phenolic compounds by 2,4,6-trichloro-1,3,5-triazine with Zn(CN)2 in the presence of a nickel precatalyst afforded the aromatic nitriles in good to excellent yields.

  利用相对无毒的Zn（CN）2作为氰化物源，开发了一种新颖，高效的镍催化的酚类化合物镍脱氧氰化方法。2,4,6-三氯-1,3,5-三嗪与C（O）活化的酚类化合物在镍预催化剂存在下与Zn（CN）2的反应获得了芳香腈，收率很好。

表征谱图