2-乙炔基苯甲腈 | 40888-26-4

• 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-乙炔基苯甲腈
• 英文名称: 2-ethynylbenzonitrile
• 英文别名: 2-cyanophenylacetylene
• CAS: 40888-26-4
• 化学式: C₉H₅N
• 分子量: 127.145
• InChiKey: LZSDQLUEGYXDCW-UHFFFAOYSA-N

物化性质

• 熔点：
  76 °C
• 沸点：
  246.8±23.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• 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：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Ethynyl-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-Ethynyl-benzonitrile
CAS number: 40888-26-4

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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, refrigerated.
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: C9H5N
Molecular weight: 127.1

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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-乙炔基苯甲腈 在 2-甲基吡啶氧化物 、 亚硝酸特丁酯 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到1,2-二氰基苯
  参考文献：
  名称：

  使用叔丁基亚硝酸盐从炔烃中制得的芳基腈：无金属方法裂解C≡C键

  摘要：

  炔烃复分解之外的炔烃C≡C键断裂仍然是反应发现中一个不发达的领域。最近，据报道氮化可以使炔烃生成腈。报道了用于末端炔烃的无金属C≡C键裂解以产生腈的新方案。这种方法提供了一个机会来合成范围广泛的包含芳基，杂芳基和天然产物衍生物的腈（38个例子）。另外，证明了t BuONO用作末端芳基炔烃的强大氮化剂的潜力。

  DOI：

  10.1021/acs.orglett.6b00147
• 作为产物：
  描述：

  2-溴苯腈 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 反应 17.0h， 生成 2-乙炔基苯甲腈
  参考文献：
  名称：

  可见光下 2-炔基芳基腈的光氧化还原自由基级联环化：直接获得 3-氨基-1-茚酮

  摘要：

  证明了通过自由基级联环化策略光诱导直接合成 3-氨基-1-茚酮。该方法涉及 2-炔基芳基腈和 N-氨基吡啶鎓盐之间的多米诺反应，并捕获可见光下原位生成的氮中心自由基 (NCR) 的反应性。包括 C-N、C-C 和 C-O 在内的多个成键事件在 2-炔基芳基腈上依次发生，从而能够在室温下以 35-76% 的产率构建 3-氨基-1-茚酮核。对合成化合物的初步生物筛选表明它们具有有效的抗癌特性。

  DOI：

  10.1002/adsc.202400026

文献信息

• [EN] DISUBSTITUTED OCTAHY-DROPYRROLO [3,4-C] PYRROLES AS OREXIN RECEPTOR MODULATORS<br/>[FR] OCTAHYDROPYRROLO [3,4-C] PYRROLES DISUBSTITUÉS UTILISÉS COMME MODULATEURS DU RÉCEPTEUR DE L'OREXINE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2012145581A1

  公开（公告）日：2012-10-26

  Disubstituted octahydropyrrolo[3,4-c]pyrrole compounds are described, which are useful as orexin receptor modulators. Such compounds may be useful in pharmaceutical compositions and methods for the treatment of diseased states, disorders, and conditions mediated by orexin activity, such as insomnia.

  描述了二取代的八氢吡咯[3,4-c]吡咯化合物，这些化合物可用作促进睡眠素受体的调节剂。这些化合物可能在药物组合物和治疗由促进睡眠素活性介导的疾病状态、紊乱和病况的方法中有用，比如失眠。
• Gold(<scp>i</scp>)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
  作者：Manjur O. Akram、Popat S. Shinde、Chetan C. Chintawar、Nitin T. Patil

  DOI：10.1039/c8ob00630j

  日期：——

  Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium

  描述了金（I）催化的芳基重氮盐与有机锡烷的交叉偶联反应。这种氧化还原中性策略为各种联芳基，乙烯基芳烃和芳基乙炔提供了一种有效的方法。用NMR和ESI-MS监测反应为原位形成Ph 3 PAu I R（R =芳基，乙烯基和炔基）物种提供了有力证据，这对于激活芳基重氮盐至关重要。
• New Fluorophores with Rod-Shaped Polycyano π-Conjugated Structures:  Synthesis and Photophysical Properties
  作者：Yoshihiro Yamaguchi、Takanori Ochi、Tateaki Wakamiya、Yoshio Matsubara、Zen-ichi Yoshida

  DOI：10.1021/ol0528991

  日期：2006.2.1

  the emission efficiency (Phi(f)) of OPEs. By the end donor modification, we achieved the creation of very intense blue light-emitting fluorophore with the SMe group (Phi(f) = 0.972, log epsilon 4.89, lambda(em) 455 nm) and very intense yellow light-emitting fluorophore with the NMe(2) group (Phi(f) = 0.999, log epsilon 4.75, lambda(em) 555 nm). Contrasting Phi(f) solvent dependency of 6 and 7 and a linear

  [反应：见正文]通过Pd交叉偶联反应合成了新型棒状聚氰基-低聚（亚苯基乙炔基）。发现多氰基基团极大地提高了OPE的发射效率（Phi（f））。通过最终的供体修饰，我们实现了具有SMe基团（Phi（f）= 0.972，对数epsilon 4.89，λ（em）455 nm）的非常强的蓝色发光荧光团的创建，以及NMe（2）组（Phi（f）= 0.999，log epsilon 4.75，lambda（em）555 nm）。还发现6和7的Phi（f）溶剂依赖性相反，并且在整个sigma（p）-X区域中，Phi（f）和sigma（p）-X之间存在线性关系。
• A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine
  作者：Guilong Tian、Liangliang Song、Zhenghua Li、Koen Robeyns、Luc Van Meervelt、Erik V. Van der Eycken

  DOI：10.1021/acs.orglett.0c03062

  日期：2020.11.6

  procedure for the synthesis of highly functionalized N-heterocyclic 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones has been elaborated through a gold-catalyzed tandem hydroamination/cycloisomerization cascade. This novel and highly efficient method allows the rapid construction of these diverse N-heterocyclic scaffolds starting from readily available building blocks, and shows a wide scope

  通过金催化串联加氢胺化/环异构化级联，详细阐述了合成高度官能化的 N-杂环 1,6-环 2-吡啶酮和 2,3-环 4-嘧啶酮的简洁而灵活的程序。这种新颖且高效的方法允许从现成的构建块开始快速构建这些不同的 N-杂环支架，并显示出广泛的范围和良好的官能团耐受性。(±)-seco-antofine 和 (±)-septine 的全合成是采用这种策略实现的。
• Synthesis of Pyrrolo[1,2-<i>b</i>]isoquinolines via Gold(I)-Catalyzed Cyclization/Enyne Cycloisomerization/1,2-Migration Cascade
  作者：Liangliang Song、Guilong Tian、Luc Van Meervelt、Erik V. Van der Eycken

  DOI：10.1021/acs.orglett.0c02310

  日期：2020.8.21

  of the migrating group is comprehensively investigated. The study of the mechanism indicates that the pathway involving a gold carbenoid species is the main pathway and that the 1,2-migration of alkyl and aryl groups to the gold carbenoid occurs in an intramolecular fashion. This cascade reaction is also employed as the key step for the synthesis of a decumbenine B analogue.

  开发了金（I）催化的N-炔基2-乙酰胺的级联转化，用于快速有效地合成吲哚并立定支架。通过顺序的亲核环化/烯炔环异构化/ 1,2-迁移过程，各种吡咯并[1,2- b]异喹啉在温和条件下以区域特异性和会聚的方式获得。在此过程中可以耐受各种烷基和芳基迁移基团。全面研究了迁移组的电子效应。对机理的研究表明，涉及金类胡萝卜素的途径是主要途径，并且烷基和芳基的1，2-迁移以分子内方式发生。该级联反应也被用作合成癸二烯B类似物的关键步骤。