2-氰基联苯 | 24973-49-7

• 物质功能分类: 有机原料 - 腈类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氰基联苯
• 中文别名: [1,1'-联苯]-2-甲腈
• 英文名称: biphenyl-2-carbonitrile
• 英文别名: 2-Cyanobiphenyl；[1,1'-biphenyl]-2-carbonitrile；2-phenylbenzonitrile
• CAS: 24973-49-7
• 化学式: C₁₃H₉N
• mdl: MFCD00060669
• 分子量: 179.221
• InChiKey: WLPATYNQCGVFFH-UHFFFAOYSA-N

物化性质

• 熔点：
  35-37°C
• 沸点：
  301.75°C (rough estimate)
• 密度：
  1.1255 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2926909090
• 危险品运输编号：
  UN 3439
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P261,P273,P280,P305+P351+P338
• 危险性描述：
  H315,H318,H335,H410
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Phenylbenzonitrile
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: 2-Phenylbenzonitrile
CAS number: 24973-49-7

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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: C13H9N
Molecular weight: 179.2

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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-氰基联苯 在 sodium hydroxide 、 盐酸 作用下， 以 乙二醇 、 正庚烷 、 水 、 甲苯 为溶剂， 反应 16.0h， 以94.2%的产率得到二氢-3-(异十二碳烯基)呋喃-2,5-二酮
  参考文献：
  名称：

  Process for producing tert-butyl 4′-methyl-2-biphenylcarboxlate

  摘要：

  一种制备叔丁基4'-甲基-2-联苯羧酸酯的方法，其特征在于在酸催化剂存在下，将4'-甲基-2-联苯羧酸与异丁烯反应。根据本发明，在温和的反应条件下，如常温，无需复杂的程序或任何危险的溶剂，就可以方便、高效地制备高质量的叔丁基4'-甲基-2-联苯羧酸酯。

  公开号：

  US06369266B1
• 作为产物：
  描述：

  二氢-3-(异十二碳烯基)呋喃-2,5-二酮 在 氯化亚砜 、 氨 作用下， 以 水 为溶剂， 生成 2-氰基联苯
  参考文献：
  名称：

  液氨中对苯二甲腈二阴离子与联苯腈相互作用形成二氰基三联苯

  摘要：

  对苯二甲腈二价阴离子与联苯腈偶联，提供双氰基取代的对三联苯。讨论了联苯腈中氰基位置对三联苯支架结构的影响。

  DOI：

  10.3998/ark.5550190.0012.808
• 作为试剂：
  描述：

  三苯基膦 、 diisobutylaluminum hydride 、 2-溴苯腈 在 bis(acetylacetonate)nickel(II) 、 zinc chloride phenyl lithium 乙醚 、 盐酸 、 水 、 Sodium sulfate-III 、 2-氰基联苯 、 silica gel 、 正己烷 作用下， 以 四氢呋喃 为溶剂， 生成 2-氰基联苯
  参考文献：
  名称：

  Angiotensin II antagonists

  摘要：

  这项发明提供了新型杂环衍生物、它们的制药配方以及它们在哺乳动物中拮抗血管紧张素II受体的用途。

  公开号：

  US05569768A1

文献信息

• Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
  作者：Tristan Delcaillau、Philip Boehm、Bill Morandi

  DOI：10.1021/jacs.1c00529

  日期：2021.3.17

  We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications

  我们描述了芳基腈和芳基硫醚之间的新官能团复分解。催化系统镍/dcype 对于实现这种完全可逆的转化，以良好的收率至关重要。此外，不含氰化物和硫醇的反应显示出高官能团耐受性和商业分子后期衍生化的高效率。最后，合成应用证明了它在多步合成中的多功能性和实用性。
• Polyaniline-anchored palladium catalyst-mediated Mizoroki-Heck and Suzuki-Miyaura reactions and one-pot Wittig-Heck and Wittig-Suzuki reactions
  作者：Heta A. Patel、Arun L. Patel、Ashutosh V. Bedekar

  DOI：10.1002/aoc.3234

  日期：2015.1

  A polyaniline‐anchored palladium catalyst was prepared and screened for coupling reactions of aryl halides. The robust and recyclable catalyst was effective in Mizoroki–Heck and Suzuki–Miyaura reactions of aryl bromides and aryl iodides. The catalyst system was further employed for one‐pot Wittig–Heck and Wittig–Suzuki combinations to build conjugated compounds in good conversions. Copyright © 2014

  制备了聚苯胺锚定的钯催化剂，并筛选了芳基卤化物的偶联反应。坚固且可回收的催化剂在芳基溴化物和芳基碘化物的Mizoroki-Heck和Suzuki-Miyaura反应中有效。该催化剂体系还用于单罐Wittig-Heck和Wittig-Suzuki组合，以良好的转化率构建共轭化合物。版权所有©2014 John Wiley＆Sons，Ltd.
• Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile, and iodine under metal cyanide-free conditions
  作者：Ko Uchida、Hideo Togo

  DOI：10.1016/j.tet.2019.130550

  日期：2019.9

  by the treatment of aryl bromides with n-butyllithium and then pivalonitrile, followed by the treatment with molecular iodine at 70 °C, without metal cyanides under transition-metal-free conditions. The present reaction proceeds through the radical β-elimination of imino-nitrogen-centered radicals formed from the reactions of imines and N-iodoimines under warming conditions. © 2019 Elsevier Science

  通过先用正丁基锂然后再用新戊腈处理芳基溴化物，然后在无过渡金属的条件下用分子碘在70°C的温度下处理（不使用金属氰化物），可以以高收率获得各种芳族腈。本反应通过在加热条件下由亚胺和N-碘亚胺的反应形成的以亚氨基氮为中心的自由基的β-消除进行。分级为4 +©2019 Elsevier Science。版权所有。
• Highly Active Monoligated Arylpalladacyles for Cross-Coupling Reactions
  作者：Chunming Zhang、Kelli Ogawa、Siyu Tu、Chengli Zu、Jim Ringer、Chris Derstine、Hien Do、Philip P. Fontaine、Jerzy Klosin

  DOI：10.1021/acs.oprd.9b00234

  日期：2019.10.18

  for a range of aryl halide and boronate coupling partners. Notably, aryl chlorides are viable coupling partners even under relatively mild conditions at short reaction times (e.g., 1 h at 60 °C). One of the best catalysts described here exhibits improved turnover frequency for a particularly difficult coupling reaction involving an aryl chloride and a sterically congested boronic ester.

  已经开发了一系列具有酰胺，尿素和氨基甲酸酯骨架的新型单连接芳基四环复合物，发现它们对Suzuki-Miyaura交叉偶联具有很高的活性。这些Palladacycle预催化剂衍生自简单，廉价的原料，并且对空气和湿气稳定。在测试的那些中最活跃的同类物是基于尿素的palladacycles，它与t Bu 3一起使用。P配体可诱导一系列芳基卤和硼酸酯偶联伙伴的高转化率。值得注意的是，即使在相对温和的条件下，较短的反应时间（例如，在60°C下1 h），芳基氯化物也是可行的偶合伴侣。这里描述的最好的催化剂之一对于特别困难的偶合反应表现出改善的周转频率，所述偶合反应涉及芳基氯和空间拥挤的硼酸酯。
• Synthesis of Amido-N-imidazolium Salts and their Applications as Ligands in Suzuki-Miyaura Reactions: Coupling of Hetero- aromatic Halides and the Synthesis of Milrinone and Irbesartan
  作者：Manian Rajesh Kumar、Kyungho Park、Sunwoo Lee

  DOI：10.1002/adsc.201000592

  日期：2010.12.17

  catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki–Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki–Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to

  描述了基于钯-酰胺基-N-杂环卡宾的Suzuki-Miyaura杂芳基溴化物偶联反应的新催化体系。从相应的苯胺以高收率合成了各种空间庞大的酰胺基-N-咪唑鎓盐。该催化体系有效地促进了杂芳基溴化物和氯化物与一系列硼酸的Suzuki-Miyaura偶联，从而以高收率得到了相应的芳基化合物。随着取代基空间位阻的增加，产率增加。特别是，1-（2,6-二异丙基）-3- ñ - （2,4,6-三-叔-butylphenylacetamido）咪唑鎓溴化物（4BC）在2-溴吡啶和苯基硼酸的偶联反应中显示出850,000 TON。此外，药物化合物如米力农和厄贝沙坦是通过Suzuki-Miyaura偶联，使用体积庞大的酰胺基-N-咪唑鎓盐（4bc）作为配体合成的。

表征谱图