4’-氯-4-氰基联苯 | 57774-36-4

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 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: 4’-氯-4-氰基联苯
• 中文别名: 4-(4-氯苯基)苄腈；4'-氯-4-氰基联苯
• 英文名称: 4-(4'-chlorophenyl)benzonitrile
• 英文别名: 4'-chloro-[1,1'-biphenyl]-4-carbonitrile；4-chloro-4'-cyanobiphenyl；4'-chlorobiphenyl-4-carbonitrile；4′-chloro-[1,1′-biphenyl]-4-carbonitrile；4-(4-Chlorophenyl)benzonitrile
• CAS: 57774-36-4
• 化学式: C₁₃H₈ClN
• 分子量: 213.666
• InChiKey: DVLCPRBAOHXYIQ-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  359.8±25.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H312,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(4-Chlorophenyl)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-(4-Chlorophenyl)benzonitrile
CAS number: 57774-36-4

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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.
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: C13H8ClN
Molecular weight: 213.7

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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, hydrogen chloride.

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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：

  4’-氯-4-氰基联苯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到[4-(4-氯苯基)苯基]甲胺
  参考文献：
  名称：

  Lead Optimization of a Novel Series of Imidazo[1,2-a]pyridine Amides Leading to a Clinical Candidate (Q203) as a Multi- and Extensively-Drug-Resistant Anti-tuberculosis Agent

  摘要：

  A critical unmet clinical need to combat the global tuberculosis epidemic is the development of potent agents capable of reducing the time of multi-drug-resistant (MDR) and extensively-drug-resistant (XDR) tuberculosis therapy. In this paper, we report on the optimization of imidazo[1,2-a]pyridine amide (IPA) lead compound 1, which led to the design and synthesis of Q203 (50). We found that the amide linker with IPA core is very important for activity against Mycobacterium tuberculosis H37Rv. Linearity and lipophilicity of the amine part in the IPA series play a critical role in improving in vitro and in vivo efficacy and pharmacokinetic profile. The optimized IPAs 49 and 50 showed not only excellent oral bioavailability (80.2% and 90.7%, respectively) with high exposure of the area under curve (AUC) but also displayed significant colony-forming unit (CFU) reduction (1.52 and 3.13 log10 reduction at 10 mg/kg dosing level, respectively) in mouse lung.

  DOI：

  10.1021/jm5003606
• 作为产物：
  描述：

  4-氰基苯磺酰氯 在 potassium phosphate 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 4’-氯-4-氰基联苯
  参考文献：
  名称：

  N,N-二磺酰甲胺和芳基硼酸的镍催化脱硫 Suzuki-Miyaura 交叉偶联

  摘要：

  已开发出一种用于从 N,N-二磺酰基甲胺和芳基硼酸合成联芳基化合物的镍催化方法。代替芳烃磺酰氯，使用各种 N,N-二磺酰甲胺作为芳基源，通过 SO2 的挤出得到中等至良好产率的交叉偶联产物。

  DOI：

  10.1002/ejoc.201402919

文献信息

• Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis
  作者：Fengze Wang、Chen Wang、Guoping Sun、Gang Zou

  DOI：10.1016/j.tetlet.2019.151491

  日期：2020.2

  A highly efficient cross-coupling of cost-effective diarylborinic acids with both isolatable and latent arenediazoniums, i.e. tetrafluoroborates and aryltriazenes, respectively, has been developed with a practical palladium catalyst system under base-free conditions in open flask at room temperature. A variety of electronically and sterically various biaryls, in particular, those bearing a coordinative

  低成本的二芳基硼酸与可分离的和潜在的芳族重氮鎓（即四氟硼酸酯和芳基三氮烯）的高效交叉偶联已在实用的钯催化剂体系下，在无碱条件下于室温下在敞口烧瓶中开发出来。通过使用0.3mol％的乙酸钯作为催化剂，可以以良好或优异的产率获得多种电子和空间上不同的联芳基，特别是那些带有配位邻位取代基的联芳基。该方案的特征包括二芳基硼酸的成本效益，对杂原子邻位取代底物的功效以及对芳基氯化物的高化学选择性，已在杀菌剂Boscalid的实际合成中得到了明确证明。
• Nickel-Catalyzed Monoarylation of Ammonia
  作者：Andrey Borzenko、Nicolas L. Rotta-Loria、Preston M. MacQueen、Christopher M. Lavoie、Robert McDonald、Mark Stradiotto

  DOI：10.1002/anie.201410875

  日期：2015.3.16

  diverse (hetero)aryl chloride, bromide, and tosylate electrophiles were employed in the Ni‐catalyzed monoarylation of ammonia, including chemoselective transformations. The employed JosiPhos/[Ni(cod)2] catalyst system enables the use of commercially available stock solutions of ammonia, or the use of ammonia gas in these reactions, thereby demonstrating the versatility and potential scalability of the reported

  结构多样的（杂）芳基氯，溴化物和甲苯磺酸盐亲电子体被用于Ni催化的氨单芳基化反应，包括化学选择性转化。所采用的JosiPhos / [Ni（cod）2 ]催化剂体系使得能够使用市售的氨气储备溶液，或在这些反应中使用氨气，从而证明了所报道方案的多功能性和潜在的可扩展性。原理验证实验证明，空气稳定的[（JosiPhos）NiCl 2 ]预催化剂可成功用于此类转化。
• Nitro group reduction and Suzuki reaction catalysed by palladium supported on magnetic nanoparticles modified with carbon quantum dots generated from glycerol and urea
  作者：Mohammad Gholinejad、Fatemeh Zareh、Carmen Nájera

  DOI：10.1002/aoc.3984

  日期：2018.1

  stabilization of palladium species and the prepared catalyst, Pd@CQD@Fe3O4, was characterized using various techniques. This magnetic supported palladium was applied as an efficient catalyst for the reduction of aromatic nitro compounds to primary amines at room temperature using very low palladium loading (0.008 mol%) and also for the Suzuki–Miyaura cross‐coupling reaction of aryl halides as well as challenging

  甘油和尿素用作绿色廉价的碳量子点（CQD）来源，用于修饰Fe 3 O 4纳米颗粒（NPs）。所获得的CQD @ Fe 3 O 4 NP用于稳定钯物质和制备的催化剂Pd @ CQD @ Fe 3 O 4。，使用各种技术进行了表征。这种磁性负载的钯被用作有效的催化剂，用于在室温下使用极低的钯负载量（0.008 mol％）将芳族硝基化合物还原为伯胺，以及用于芳烃卤化物的Suzuki-Miyaura交叉偶联反应以及具有挑战性的杂芳基溴化物和芳基重氮盐与芳基硼酸和苯基三氟硼酸钾。回收了这种可磁循环的催化剂，并将其连续7次重复使用，以将4-硝基甲苯还原为p甲苯胺和4-碘苯甲醚与苯基硼酸的反应连续十次，活性降低很小。使用透射电子显微镜，振动样品磁力分析和X射线光电子能谱对在铃木反应中重复使用的催化剂进行了表征。通过热过滤和中毒试验等实验，已经证明，根据活性钯物质的释放-返回途径，真正的催化剂可以在均相条件下工作。
• 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。
• Ligand-free palladium catalyzed Ullmann biaryl synthesis: ‘household’ reagents and mild reaction conditions
  作者：Xinchi Gong、Jie Wu、Yunge Meng、Yulan Zhang、Long-Wu Ye、Chunyin Zhu

  DOI：10.1039/c8gc03862g

  日期：——

  palladium catalysed Ullmann biaryl synthesis has been developed using hydrazine hydrate as the reducing reagent at room temperature. The combination of Pd(OAc)2 and hydrazine hydrate works smoothly for the coupling of both electron-rich and electron-deficient aryl iodides, as well as hetero-aryl iodides, leading to a wide range of biaryls in good to excellent yields. The reaction requires only 1 mol% Pd(OAc)2

  在室温下，使用水合肼作为还原剂，已经开发了钯催化的乌尔曼联芳基合成。Pd（OAc）2和水合肼的组合对于富电子和缺电子的芳基碘化物以及杂芳基碘化物的偶联均能顺利发挥作用，从而产生了范围广泛的联芳基，收率高至优异。该反应仅需要1mol％的Pd（OAc）2，并且发现原位产生的钯纳米颗粒是活性催化剂。