2-(2-氰基苯基)苯甲腈 | 4341-02-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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-(2-氰基苯基)苯甲腈
• 英文名称: biphenyl-2,2'-dicarbonitrile
• 英文别名: 2,2'-dicyanobiphenyl；[1,1'-biphenyl]-2,2'-dicarbonitrile；2-(2-cyanophenyl)benzonitrile
• CAS: 4341-02-0
• 化学式: C₁₄H₈N₂
• 分子量: 204.231
• InChiKey: XDQREGRMKWTMOO-UHFFFAOYSA-N

物化性质

• 熔点：
  174 - 175°C
• 溶解度：
  氯仿（微溶）、DMSO（微溶、加热）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 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：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P501,P261,P270,P271,P264,P280,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330,P302+P352+P312,P304+P340+P312
• 危险性描述：
  H302+H312+H332,H315,H319
• 储存条件：
  室温避光保存

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(2-Cyanophenyl)benzonitrile
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-(2-Cyanophenyl)benzonitrile
CAS number: 4341-02-0

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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: C14H8N2
Molecular weight: 204.2

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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-(2-氰基苯基)苯甲腈 在 bis(trimethylsilyl)acetylenetitanocene 、 盐酸 作用下， 以 甲苯 、 乙醚 为溶剂， 反应 0.37h， 以61%的产率得到菲醌
  参考文献：
  名称：

  茂钛介导的二腈偶联：含氮多环芳烃的不同途径

  摘要：

  报道了一种用于构建大型含氮多环芳烃 (PAH) 的通用合成策略。该策略涉及两个关键步骤：（1）二茂钛介导的低聚（二腈）前体的还原环化，形成附加有二（氮杂）钛环戊二烯官能团的 PAH；(2) 发散的二茂钛转移反应，它允许将一个或多个邻醌、二唑或吡嗪单元安装到 PAH 框架中的最后一步。正如紫外/可见光和荧光光谱、循环伏安法和 DFT 计算所揭示的那样，新方法可以对 HOMO 和 LUMO 能级进行合理的后期控制，从而实现光物理和电化学特性。更一般地说，这一贡献展示了二（氮杂）金属环戊二烯中间体在有机合成中的首次生产性用途，

  DOI：

  10.1021/jacs.7b13823
• 作为产物：
  描述：

  2-溴苯腈 在 正丁基锂 、 copper dichloride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以57%的产率得到2-(2-氰基苯基)苯甲腈
  参考文献：
  名称：

  茂钛介导的二腈偶联：含氮多环芳烃的不同途径

  摘要：

  报道了一种用于构建大型含氮多环芳烃 (PAH) 的通用合成策略。该策略涉及两个关键步骤：（1）二茂钛介导的低聚（二腈）前体的还原环化，形成附加有二（氮杂）钛环戊二烯官能团的 PAH；(2) 发散的二茂钛转移反应，它允许将一个或多个邻醌、二唑或吡嗪单元安装到 PAH 框架中的最后一步。正如紫外/可见光和荧光光谱、循环伏安法和 DFT 计算所揭示的那样，新方法可以对 HOMO 和 LUMO 能级进行合理的后期控制，从而实现光物理和电化学特性。更一般地说，这一贡献展示了二（氮杂）金属环戊二烯中间体在有机合成中的首次生产性用途，

  DOI：

  10.1021/jacs.7b13823

文献信息

• 1,3,5-Triazapentadienes by Nucleophilic Addition to 1,3- and 1,4-Dinitriles—Sterically Constrained Examples by Incorporation into Cyclic Peripheries: Synthesis, Aggregation, and Photophysical Properties
  作者：Agnes Johanna Wrobel、Ralph Lucchesi、Birgit Wibbeling、Constantin-Gabriel Daniliuc、Roland Fröhlich、Ernst-Ulrich Würthwein

  DOI：10.1021/acs.joc.6b00126

  日期：2016.4.1

  with the two cyano groups in 1,3 or 1,4 distance. These novel compounds show very strong tendency for aggregation due to hydrogen bonding, especially to form homodimers as seen from X-ray data in the solid state. Additional hydrogen bonding generates also linear chains in the crystal. Several of the new compounds show fluorescence in solution. Quantum chemical DFT calculations were used for evaluation

  由于主要的n /π*相互作用，1,3,5-三氮杂戊二烯通常在N–C–N–C–N骨架上呈U形或扭曲的S形构象。但是，如果1,3,5-三氮杂戊二烯单元是环的一部分，则其W构象可能仅限于平面。在这里，我们描述了13个新的1,3,5- triazapentadienes合成10 - 12，它们在空间上通过掺入抑制成六元或七元环系统，通过加入锂化的伯胺或肼的5到二腈7，8或9两个氰基的距离为1,3或1,4。这些新型化合物由于氢键而显示出非常强的聚集趋势，尤其是从固态X射线数据可以看出，它们形成同二聚体。额外的氢键还在晶体中产生线性链。几种新化合物在溶液中显示荧光。量子化学DFT计算用于评估二聚能和光物理性质的解释。
• Nickel-Catalyzed Cyanation of Aryl Chlorides and Triflates Using Butyronitrile: Merging Retro-hydrocyanation with Cross-Coupling
  作者：Peng Yu、Bill Morandi

  DOI：10.1002/anie.201707517

  日期：2017.12.4

  We describe a nickel‐catalyzed cyanation reaction of aryl (pseudo)halides that employs butyronitrile as a cyanating reagent instead of highly toxic cyanide salts. A dual catalytic cycle merging retro‐hydrocyanation and cross‐coupling enables the conversion of a broad array of aryl chlorides and aryl/vinyl triflates into their corresponding nitriles. This new reaction provides a strategically distinct

  我们描述了芳基（假）卤化物的镍催化氰化反应，该反应采用丁腈作为氰化试剂代替剧毒的氰化物盐。将逆向氢氰化和交叉偶联相结合的双催化循环可将多种芳基氯和芳基/乙烯基三氟甲磺酸转化为相应的腈。该新反应为安全制备芳基氰化物提供了战略上独特的方法，芳基氰化物是农业化学和药物化学中必不可少的化合物。
• Carbopalladation of Nitriles:  Synthesis of Benzocyclic Ketones and Cyclopentenones via Pd-Catalyzed Cyclization of ω-(2-Iodoaryl)alkanenitriles and Related Compounds
  作者：Alexandre A. Pletnev、Richard C. Larock

  DOI：10.1021/jo0262006

  日期：2002.12.1

  An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This methodology has been extended to the synthesis of tetralones and cyclopentenones.

  已经开发出一种通过腈的分子内碳弹头化合成2，2-二取代的苯并环酮的有效方法。取代的3-（2-碘芳基）丙烷腈的环化以高收率提供茚满酮。该反应与多种官能团相容。该方法已经扩展到四氢萘酮和环戊烯酮的合成。
• Convenient synthesis of organic-electronics-oriented building blocks via on-water and under-air homocoupling of (hetero)aryl iodides
  作者：Yi-An Chen、Ching-Yuan Liu

  DOI：10.1039/c5ra13517f

  日期：——

  operationally simple homocoupling reaction that targets the convenient synthesis of organic-electronically important building blocks. A variety of synthetically useful bithiophene derivatives and functionalized biphenyls are efficiently prepared by an on-water and under-air protocol using Pd/C as catalyst. We find that Pd/C gives generally higher and cleaner homocoupling conversions than using Pd(OAc)2 in the

  我们在此报告了一种操作简单的均偶联反应，其目标是方便合成有机电子重要的结构单元。各种合成上有用的联噻吩衍生物和官能化联苯可通过水上和空气中协议使用Pd / C作为催化剂有效地制备。我们发现，在（杂）芳基碘化物的情况下，由于Pd（OAc）2的存在，与使用Pd（OAc）2相比，Pd / C的同质耦合转化率更高且更清洁。引发更多的副反应，包括脱卤和低聚。在最佳条件下，对酯，酮，醛，腈，硝基，氯和溴等官能团的耐受性良好。我们希望本方法学将为绿色化学与基于噻吩的有机材料的桥接做出宝贵的合成贡献。
• [EN] BIARYLMETHYL HETEROCYCLES<br/>[FR] HÉTÉROCYCLES BIARYLMÉTHYLES
  申请人：UNIV MONTREAL

  公开号：WO2018005591A1

  公开（公告）日：2018-01-04

  The present invention provides compounds of Formula (I): wherein all variables are as defined in the specification, and compositions comprising any of such novel compounds. These compounds are biased agonists, or β-Arrestin agonists of the angiotensin II receptor, which may be used as medicaments.

  本发明提供了式(I)的化合物：其中所有变量如规范中所定义，并包括任何此类新化合物的组合物。这些化合物是肾素II受体的偏倚激动剂，或β-阻滞素激动剂，可用作药物。

表征谱图