2-(4-氯苯基)苯甲腈 | 89346-58-7

• 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-(4-氯苯基)苯甲腈
• 英文名称: 4'-chloro-[1,1'-biphenyl]-2-carbonitrile
• 英文别名: 4'-chloro-2-cyanobiphenyl；4'-chlorobiphenyl-2-carbonitrile；2-(4-Chlorophenyl)benzonitrile
• CAS: 89346-58-7
• 化学式: C₁₃H₈ClN
• 分子量: 213.666
• InChiKey: ZNYVLXVPKPEZLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-(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: 2-(4-Chlorophenyl)benzonitrile
CAS number: 89346-58-7

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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: 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：

  2-(4-氯苯基)苯甲腈 在 双氧水 、 sodium hydroxide 、 sodium hypochlorite 作用下， 以 乙醇 、 水 为溶剂， 以82%的产率得到4-氯联苯-2-胺盐酸盐
  参考文献：
  名称：

  高度实用和可靠的镍催化剂，用于芳基卤化物的Suzuki-Miyaura偶联

  摘要：

  我们公开了[1,3-双（二苯基膦基）甲烷]氯化镍（II）[NiCl 2（dppp）]是一种活性高，通用，便宜且稳定的催化剂，可用于芳烃卤化物的铃木-宫浦交叉偶联反应，催化剂负载量低于1 mol％，尤其是在没有额外的支持配体的情况下。在优化的反应条件下，广泛的芳基溴化物以及众所周知的未反应的芳基氯化物，包括活化的，未活化的，失活的，杂芳族的和空间位阻的底物，都可以与各种硼酸顺利偶联（47例，第48页98％的收率）。另外，该转化耐受各种官能团，例如醚，酯，酮，醛，氰基以及未保护的氨基和羟基。最后，克规模的商业化降压药和杀菌剂几个核心结构的合成进一步证明了该方法的潜在用途。因此，NiCl具有高活性，广泛适用性，廉价和高稳定性的组合这项工作中提出的2（dppp）构成了为数不多的突出催化剂之一，这些催化剂使实用，可靠的联芳基和杂联二芳基结构具有易于获得的芳基卤化物和硼酸的结构多样性。

  DOI：

  10.1002/adsc.201100101
• 作为产物：
  描述：

  2-氰基苯硼酸 在 tripotassium phosphate "n" hydrate 、 Pd(PPh₃)₂Cl₂ 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 2-(4-氯苯基)苯甲腈
  参考文献：
  名称：

  Novel Syntheses of Fluorenones via Nitrile-Directed Palladium-Catalyzed C–H and Dual C–H Bond Activation

  摘要：

  Novel procedures for the [Pd]/[Ag]/TFA system catalyzed cascade reactions of nitrile directed remote C-H and dual C-H bond activation with insertion of nitrile were developed, which afforded variously polysubstituted fluorenones in moderate to good yields with tolerance of a wide variety of substrates.

  DOI：

  10.1021/ol401063w

文献信息

• Preparation of 6-substituted phenanthridines from o-biaryl ketoximes via the Beckmann rearrangement
  作者：Kohei Nakamura、Eiji Kobayashi、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2021.132244

  日期：2021.7

  Treatment of anti alkyl o-biaryl ketoximes and anti aryl o-biaryl ketoximes with Tf2O at 120 °C, followed by quenching with Et3N gave 6-alkylphenanthridines and 6-arylphenanthridines in good yields, respectively. These reactions proceeded through the O-triflation of the ketoximes, the Beckmann rearrangement, and the electrophilic cyclization of the formed nitrilium group onto the aromatic ring. © 2021

  在120°C下用Tf 2 O处理抗烷基邻联芳基酮肟和抗芳基邻联芳基酮肟，然后用Et 3 N猝灭，分别以良好的产率得到6-烷基菲啶和6-芳基菲啶。这些反应通过酮肟的O-三氟甲磺酸化、贝克曼重排和形成的腈基在芳环上的亲电环化进行。© 2021 爱思唯尔科学。版权所有。
• Preparation of phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides with 1,3-diiodo-5,5-dimethylhydantoin
  作者：Kei Yanai、Hideo Togo

  DOI：10.1016/j.tet.2020.131503

  日期：2020.10

  6-arylphenanthridines and 6-unsubstituted phenanthridines in good to moderate yields, respectively. The reaction proceeds through an oxidative cyclization onto the aromatic ring by sulfonamidyl radicals formed from the N-iodosulfonamides. The present reaction is a one-pot method for the preparation of both 6-arylphenanthridines and 6-unsubstituted phenanthridines from N-(o-arylbenzyl)trifluoromethanesulfonamides

  在钨灯的照射下，在1,2-二氯乙烷中用1,3-二碘-5,5-二甲基乙内酰脲处理N-（邻芳基苄基）三氟甲磺酰胺，然后与t BuOK反应，得到相应的6-芳基菲啶和6 -未取代的菲啶分别以良好至中等的产率。该反应通过由N-碘磺酰胺形成的磺酰胺基，通过氧化环化反应进行到芳环上。本反应是一锅法，可从N-（o）制备6-芳基菲啶和6-未取代的菲啶-芳基苄基）三氟甲磺酰胺在无过渡金属的条件下。©2020爱思唯尔科学。版权所有。
• Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone
  作者：Ilya A P Jourjine、Lukas Zeisel、Jürgen Krauß、Franz Bracher

  DOI：10.3762/bjoc.17.181

  日期：——

  Highly substituted fluorenones are readily prepared in mostly fair to good yields via metal- and additive-free TBHP-promoted cross-dehydrogenative coupling (CDC) of readily accessible N-methyl-2-(aminomethyl)biphenyls and 2-(aminomethyl)biphenyls. This methodology is compatible with numerous functional groups (methoxy, cyano, nitro, chloro, and SEM and TBS-protective groups for phenols) and was further

  通过不含金属和添加剂的 TBHP 促进的易于获得的N-甲基-2-(氨甲基)联苯和 2-(氨甲基)联苯的交叉脱氢偶联 (CDC)，可以轻松制备高度取代的芴酮，收率基本上相当到良好。该方法与多种官能团（甲氧基、氰基、硝基、氯以及苯酚的 SEM 和 TBS 保护基团）兼容，并进一步用于天然产物诺比隆的首次全合成。
• Rational Development of Remote C−H Functionalization of Biphenyl: Experimental and Computational Studies
  作者：Zhoulong Fan、Katherine L. Bay、Xiangyang Chen、Zhe Zhuang、Han Seul Park、Kap‐Sun Yeung、K. N. Houk、Jin‐Quan Yu

  DOI：10.1002/anie.201915624

  日期：2020.3.16

  compounds is reported. Compared to the previous approach of installing a complex U-shaped template to achieve a molecular U-turn and assemble the large-sized cyclophane transition state for the remote C-H activation, a synthetically useful phenyl nitrile functional group could also direct remote meta-C-H activation. This reaction provides a useful method for the modification of biaryl compounds because

  报道了一种简单而有效的腈引导的间-CH烯化、乙酰氧基化和联芳基化合物的碘化。与之前安装复杂的U型模板以实现分子掉头并组装大尺寸环芳过渡态以进行远程CH活化的方法相比，合成有用的苯基腈官能团也可以直接远程间位CH活化。该反应为联芳基化合物的改性提供了一种有用的方法，因为腈基可以很容易地转化为胺、酸、酰胺或其他杂环。值得注意的是，从之前使用大环芳腈模板的结果中无法预期联苯腈的远程间位选择性。DFT 计算研究表明，含有配体的 Pd-Ag 异二聚过渡态 (TS) 有利于所需的远程元选择性。对照实验证明了腈基团的定向作用并排除了非定向元-CH激活的可能性。研究发现，取代的 2-吡啶酮配体在协同金属化-去质子化 (CMD) 过程中协助间位 CH 键断裂的关键。
• Pd-Catalysed Suzuki–Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides
  作者：Patrizio Orecchia、Desislava Slavcheva Petkova、Roland Goetz、Frank Rominger、A. Stephen K. Hashmi、Thomas Schaub

  DOI：10.1039/d1gc02602j

  日期：——

  The Suzuki–Miyaura coupling reaction of electron-poor aryl chlorides in the synthesis of crop protection-relevant active ingredients in water is disclosed. Optimisation of the reaction conditions allowed running the reaction with 50 ppm of Pd-catalyst loading without an additional organic solvent in the cross-coupling reaction step in short reaction times. The system was optimised for the initial cross-coupling

  公开了缺电子芳基氯化物在水中合成作物保护相关活性成分中的 Suzuki-Miyaura 偶联反应。反应条件的优化允许在较短的反应时间内在交叉偶联反应步骤中以 50 ppm 的 Pd 催化剂负载量进行反应，而无需额外的有机溶剂。该系统针对大规模生产的杀菌剂啶酰菌胺、氟吡菌胺和联苯吡菌胺的初始交叉偶联步骤进行了优化，产率高达 97%。还表明，在后处理中使用对环境无害的溶剂进行简单的产物分离和纯化，可以轻松地将 Suzuki-Miyaura 反应放大到 50 g。为了展示这种方法的可用性，它被额外应用于所需活性成分的三步合成。