2-苯基-3-氰基吡啶 | 39065-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-苯基-3-氰基吡啶
• 英文名称: 2-phenylnicotinonitrile
• 英文别名: 3-cyano-2-phenylpyridine；2-phenylpyridine-3-carbonitrile
• CAS: 39065-49-1
• 化学式: C₁₂H₈N₂
• 分子量: 180.209
• InChiKey: VLXSSSFLMFXUJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 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：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Phenylpyridine-3-carbonitrile
Synonyms: 3-Cyano-2-phenylpyridine

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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: 2-Phenylpyridine-3-carbonitrile
CAS number: 39065-49-1

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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.
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: C12H8N2
Molecular weight: 180.2

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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

反应信息

• 作为反应物：
  描述：

  2-苯基-3-氰基吡啶 在 盐酸 、 水 作用下， 反应 151.0h， 生成 4-氮杂-9-芴酮
  参考文献：
  名称：

  铱催化配体控制的远程对位选择性 C-H 活化和扭曲芳族酰胺的硼化

  摘要：

  报道了芳族酰胺的高度对位选择性 C-H 硼基化。对位硼化通过扭曲的芳香酰胺和新设计的配体框架（defa）之间前所未有的底物-配体扭曲进行，这与标准的硼化配体不同。使用这种 defa 配体开发了一种新型催化系统，该配体对一系列芳族酰胺表现出优异的对位选择性。

  DOI：

  10.1002/anie.202203539
• 作为产物：
  描述：

  以 硝基苯 为溶剂， 反应 5.0h， 以64%的产率得到2-苯基-3-氰基吡啶
  参考文献：
  名称：

  N-炔丙基烯胺的热环化合成无过渡金属的吡啶衍生物

  摘要：

  通过N-炔丙基烯胺的6-内-挖-环化，开发了无过渡金属合成吡啶衍生物。该方法是环境友好的，并且是高度原子经济的反应，通过在没有添加剂的溶剂中加热N-炔丙基烯胺，可以容易地获得吡啶衍生物以中等至良好的产率。使用该方法，仅需两个步骤，即可以51％的收率完成Onychine的全合成。

  DOI：

  10.1055/s-0039-1691575

文献信息

• Thrombin inhibitors
  申请人：——

  公开号：US20020119992A1

  公开（公告）日：2002-08-29

  Compounds of the invention are useful in inhibiting thrombin and associated thrombotic occlusions having the following structure: 1 or a pharmaceutically acceptable salt thereof, e.g. where R 3 is —CH 2 NH 2 , —CH 2 CH 2 NH 2 , or —CH 2 NHC(O)OC(CH 3 ) 3 .

  该发明的化合物在抑制凝血酶和相关血栓闭塞方面具有以下结构： 1 或其药用可接受的盐，例如其中R 3 为—CH 2 NH 2 ，—CH 2 CH 2 NH 2 ，或—CH 2 NHC(O)OC(CH 3 ) 3 。
• A Novel, Air-Stable Phosphine Ligand for the Palladium-Catalyzed Suzuki−Miyaura Cross-Coupling Reaction of Chloro Arenes
  作者：Raju Ghosh、N. N. Adarsh、Amitabha Sarkar

  DOI：10.1021/jo100643j

  日期：2010.8.6

  A novel, air-stable phosphine ligand, prepared from readily available 2-bromonitrobenzene and vinylmagnesium bromide, combines with Pd(CH3CN)2Cl2 to afford an effective catalyst for Suzuki−Miyaura cross-coupling of aryl, heteroaryl, and allyl chlorides with phenylboronic acid.

  由易于获得的2-溴硝基苯和乙烯基溴化镁制备的新型稳定的膦配体与Pd（CH 3 CN）2 Cl 2结合使用，可为铃木-宫浦将芳基，杂芳基和烯丙基交叉偶联提供有效的催化剂氯化与苯基硼酸。
• Access to pyridines via cascade nucleophilic addition reaction of 1,2,3-triazines with activated ketones or acetonitriles
  作者：Yuan Zhang、Han Luo、Qixing Lu、Qiaoyu An、You Li、Shanshan Li、Zongyuan Tang、Baosheng Li

  DOI：10.1016/j.cclet.2020.03.075

  日期：2021.1

  cascade nucleophilic addition reactions of 1,2,3-triazines with activated acetonitriles or ketones, which were used to construct highly substituted pyridines that are not easily accessed by conventional methods. The strategy addressed some structural diversity issues currently facing medicinal chemistry, and the resulting pyridines could be used as convenient precursors for the synthesis of related pharmaceuticals

  摘要我们研究了1,2,3-三嗪与活化乙腈或酮的级联亲核加成反应，该反应用于构建传统方法不易获得的高度取代的吡啶。该策略解决了药物化学目前面临的一些结构多样性问题，所得吡啶可用作合成相关药物的方便前体。特别是，我们的方法仅需几个步骤即可应用于市售药物依托考昔和几种生物学上重要的分子的合成。
• Synthesis of (Poly)halo-Substituted Diarylsulfones through Palladium-Catalyzed C-H Bond Sulfonylation Using (Poly)Halobenzenesulfonyl Chlorides
  作者：Arpan Sasmal、Jitendra K. Bera、Henri Doucet、Jean-François Soulé

  DOI：10.1002/ejoc.201800819

  日期：2018.12.2

  A one‐step procedure for the synthesis of (poly)halo‐substituted diarylsulfones was developed. The reaction involves ortho C–H bond sulfonylation of 2‐arylpyridines with (poly)halo‐substituted benzenesulfonyl chlorides. These reaction conditions tolerated C–F, C–Cl, C–Br and even C–I bonds.

  开发了一种合成（聚）卤代二芳基砜的一步程序。该反应涉及2-芳基吡啶与（多）卤代苯磺酰氯的邻位C-H键磺酰化反应。这些反应条件可以耐受C–F，C–Cl，C–Br甚至C–I键。
• <i>N</i> -methyliminodiacetic acid as a simple and highly efficient ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling of aryl chlorides
  作者：Liang Qi、Xiuling Zhou、Xiaogang Li、Wei Li、Meiyun Lv、Mengping Guo

  DOI：10.1002/aoc.3279

  日期：2015.4

  A simple, air‐stable, inexpensive and easily prepared molecule, N‐methyliminodiacetic acid (MIDA), is reported as a ligand for palladium‐catalyzed Suzuki–Miyaura cross‐coupling reaction of phenylboronic acid with aryl chlorides. The yield of the corresponding Suzuki coupling reaction is up to around 90% at both high temperature of 80°C and room temperature under ambient atmosphere. Copyright © 2015

  据报道，N-甲基亚氨基二乙酸（MIDA）是一种简单，对空气稳定，廉价且易于制备的分子，是苯硼酸与芳基氯化物在钯催化的Suzuki-Miyaura交叉偶联反应中的配体。在80℃的高温和室温下在环境气氛下，相应的Suzuki偶联反应的产率均高达约90％。版权所有©2015 John Wiley＆Sons，Ltd.