2-甲基[1,1-联苯]-4-甲腈 | 189828-30-6

• 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-甲基[1,1-联苯]-4-甲腈
• 中文别名: 2'-甲基-1,1'-联苯-4-甲腈
• 英文名称: 4-cyano-2'-methyl-1,1'-biphenyl
• 英文别名: 2'-methyl-[1,1'-biphenyl]-4-carbonitrile；2'-methylbiphenyl-4-carbonitrile；4-cyano-2'-methylbiphenyl；4-(2-Methylphenyl)benzonitrile
• CAS: 189828-30-6
• 化学式: C₁₄H₁₁N
• mdl: MFCD05981801
• 分子量: 193.248
• InChiKey: NTJHRYFSZWZHPG-UHFFFAOYSA-N

物化性质

• 熔点：
  54-56℃ (hexane ethyl acetate )
• 沸点：
  327.0±21.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(2-Methylphenyl)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: 4-(2-Methylphenyl)benzonitrile
CAS number: 189828-30-6

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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: C14H11N
Molecular weight: 193.2

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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-甲基[1,1-联苯]-4-甲腈 在 N-溴代丁二酰亚胺(NBS) 、 羟胺 、 乙酸酐 、 caesium carbonate 、 溶剂黄146 、 三氟乙酸 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and structure–Activity relationships of benzoxazinone-Based factor Xa inhibitors

  摘要：

  A series of benzoxazinone derivatives was designed and synthesized as factor Xa inhibitors. We demonstrated that the naphthyl moiety in the aniline-based compounds I and 2 can be replaced with benzene-fused heterobicycles and biaryls to give factor Xa inhibitors with improved trypsin selectivity. The P4 modifications lead to monoamidines which are moderately active. The benzoxazinones 41-45 are potent against factor Xa, retain the improved trypsin selectivity of the corresponding aniline-based compounds, and show strong antithrombotic effect dose responsively. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(02)00927-7
• 作为产物：
  描述：

  2-甲基苯硼酸 在 palladium diacetate potassium hydrogen difluoride 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 2-甲基[1,1-联苯]-4-甲腈
  参考文献：
  名称：

  高效的无配体钯催化的芳基三氟硼酸钾的Suzuki反应。

  摘要：

  [反应：见正文]芳基-和杂芳基三氟硼酸钾与芳基或杂芳基卤化物或三氟甲磺酸酯的无配体钯催化的Suzuki交叉偶联反应非常容易进行。交叉偶合可以在甲醇或水中，在K（2）CO（3）存在下使用Pd（OAc）（2）作为催化剂的情况下进行。可以容忍各种功能基团。

  DOI：

  10.1021/ol025845p

文献信息

• Air Stable, Sterically Hindered Ferrocenyl Dialkylphosphines for Palladium-Catalyzed C−C, C−N, and C−O Bond-Forming Cross-Couplings
  作者：Noriyasu Kataoka、Quinetta Shelby、James P. Stambuli、John F. Hartwig

  DOI：10.1021/jo025732j

  日期：2002.8.1

  aryl halides coupled with acyclic or cyclic secondary alkyl- and arylamines, with primary alkyl- and arylamines, and with aryl- and primary alkylboronic acids. These last couplings provide the first general procedure for reaction of terminal alkylboronic acids with aryl halides without toxic or expensive bases. The ligand not only generates highly active palladium catalysts, but it is air stable in

  已通过两步合成程序以高收率制备了五苯基二茂铁基二叔丁基膦，并且已研究了由带有该配体的配合物催化的各种交叉偶联过程的范围。该配体为芳基卤化物胺化和Suzuki偶联产生了非常普通的钯催化剂。对于未活化的芳基溴化物或氯化物的胺化，观察到的营业额约为1000。另外，该配体的络合物在温和条件下催化形成选定的芳基醚。反应包括富电子和贫电子的芳基溴化物和氯化物。在含有该配体的催化剂的存在下，这些芳基卤化物与无环或环状仲烷基和芳基胺，伯烷基和芳基胺，以及芳基和伯烷基硼酸偶联。这些最后的偶联为末端烷基硼酸与芳基卤化物的反应提供了第一个通用方法，而没有毒性或昂贵的碱。该配体不仅产生高活性的钯催化剂，而且在溶液和固态中都是空气稳定的。该配体的钯（0）配合物也具有空气稳定性，为固体，仅与溶液中的氧气缓慢反应。
• Catalyst for aromatic C—O, C—N, and C—C bond formation
  申请人：Yale University

  公开号：US06562989B2

  公开（公告）日：2003-05-13

  The present invention is directed to a transition metal catalyst, comprising a Group 8 metal and a ligand having the structure wherein R, R′ and R″ are organic groups having 1-15 carbon atoms, n=1-5, and m=0-4. The present invention is also directed to a method of forming a compound having an aromatic or vinylic carbon-oxygen, carbon-nitrogen, or carbon-carbon bond using the above catalyst. The catalyst and the method of using the catalyst are advantageous in preparation of compounds under mild conditions of approximately room temperature and pressure.

  本发明涉及一种过渡金属催化剂，包括一种第8族金属和具有结构的配体 其中R、R'和R"是具有1-15个碳原子的有机基团，n=1-5，m=0-4。本发明还涉及一种利用上述催化剂形成具有芳香性或乙烯基碳-氧、碳-氮或碳-碳键的化合物的方法。该催化剂和使用该催化剂的方法在大约室温和压力下的温和条件下制备化合物具有优势。
• Cross-Coupling Reaction with Lithium Methyltriolborate
  作者：Yasunori Yamamoto、Kazuya Ikizakura、Hajime Ito、Norio Miyaura

  DOI：10.3390/molecules18010430

  日期：——

  We newly developed lithium methyltriolborate as an air-stable white solid that is convenient to handle. The good performance of this triolborate for metal-catalyzed bond-forming reactions was demonstrated in palladium-catalyzed cross-coupling reactions with haloarenes. Cross-coupling reaction of [MeB(OCH2)3CCH3]Li with aryl halides occurred in the presence of Pd(OAc)2/RuPhos complex in refluxing MeOH/H2O and the absence of bases.

  我们新开发了锂甲基三醇硼酸盐，它是一种空气稳定的白色固体，便于操作。在钯催化的卤代芳烃交叉耦合反应中，这种三醇硼酸盐展现出了良好的性能。在回流的甲醇/水混合物中，不加碱的情况下，[MeB(OCH₂)₃CCH₃]Li与芳基卤化物在Pd(OAc)₂/RuPhos络合物存在下发生了交叉耦合反应。
• [Pd(Cl)2{P(NC5H10)(C6H11)2}2]-A Highly Effective and Extremely Versatile Palladium-Based Negishi Catalyst that Efficiently and Reliably Operates at Low Catalyst Loadings
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/chem.201001201

  日期：——

  electronically activated, non‐activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100 °C in the presence of just 0.01 mol % of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetals, lactones, amides, anilines,

  [Pd（Cl）2 P（NC 5 H 10）（C 6 H 11）2 } 2 ]（1）已通过使市售的[Pd（cod）（Cl）2 ]反应定量制备。室温下在几分钟内在N 2中与易于制备的1-（二环己基膦酰基）哌啶在甲苯中的环辛二烯）。综合大楼1已被证明是极佳的Negishi催化剂，能够将各种电子活化，非活化，失活，空间受阻，杂环和官能化的芳基溴化物与各种（也是杂环的）芳基锌试剂定量偶联，通常在几分钟内即可完成。 100°C，仅存在0.01 mol％的催化剂。含有硝基，腈，醚，酯，羟基，羰基和羧基的芳基溴化物，以及缩醛，内酯，酰胺，苯胺，烯烃，羧酸，乙酸，吡啶和嘧啶已被成功用作偶联伙伴。此外，在两个反应伙伴中都可以容忍电子和空间变化。实验观察强烈表明分子机制是有效的。
• Palladium mediated C–H bond activation of thiosemicarbazones: Catalytic application of organopalladium complexes in C–C and C–N coupling reactions
  作者：Piyali Paul、Poulami Sengupta、Samaresh Bhattacharya

  DOI：10.1016/j.jorganchem.2012.11.010

  日期：2013.1

  structures of complexes 1, 2 and 3 have been determined. All the complexes display intense absorptions in the visible region. Catalytic activity of complexes 1, 2 and 3 toward Suzuki type C–C coupling reactions has been examined, and all three are found to efficiently activate all types of C–X bonds (X = I, Br, Cl and even F) and bring about the C–C bond formation with high yield. These complexes are also

  在与Pd（PPh 3）2 Cl 2反应时，苯甲醛硫代半碳酰胺在亚胺键周围发生几何变化，并得到混合配体配合物1，其中掺入了NS配位的硫代半碳酰胺，三苯基膦和氯化物。与二苯甲酮硫半脲和苯乙酮硫半脲进行类似的反应，没有任何几何变化，分别得到配合物2和3，其包含CNS配位的硫代半脲和三苯基膦。复合物的晶体结构1，2和3已经确定。所有的络合物在可见光区域都显示出强烈的吸收。配合物的催化活性1，2和3朝向铃木类型的C-C偶联反应已经检查，并且所有三个被发现有效地激活所有类型的C-X键（X = I，溴，氯和甚至F），并把关于高产CC键的形成。还发现这些络合物可催化芳基卤化物与伯胺或仲胺之间的CN偶联反应。尽管发现所有三种配合物都是进行C–C和C–N偶联反应的有效催化剂，但发现配合物2是比其他两种配合物更好的催化剂。