4-乙炔基苯甲腈 | 3032-92-6

• 物质功能分类: 化学试剂 - 有机试剂 - 芳烃
• 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-乙炔基苯甲腈
• 中文别名: 4-乙基苯腈；4-乙炔基苯腈；4-乙炔苯腈；4-氰基苯乙炔
• 英文名称: 4-cyanophenylacetylene
• 英文别名: 4-Ethynylbenzonitrile；1-ethynylbenzonitrile；p-cyanophenylacetylene
• CAS: 3032-92-6
• 化学式: C₉H₅N
• mdl: MFCD04974058
• 分子量: 127.145
• InChiKey: LAGNMUUUMQJXBF-UHFFFAOYSA-N

物化性质

• 熔点：
  156-160 °C(lit.)
• 沸点：
  230.2±23.0 °C(Predicted)
• 密度：
  1.037 g/mL at 25 °C(lit.)
• 闪点：
  >110 °C
• 稳定性/保质期：
  在常温常压下稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温下，请将产品存放在阴凉、通风的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Ethynylbenzonitrile
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 4-Ethynylbenzonitrile
CAS number: 3032-92-6

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels.

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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
No data
Boiling point:
Melting point: No data
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
UN Number: UN3439 Class: 6.1 Packing group: III
Proper shipping name: NITRILES, TOXIC, SOLID, N.O.S. (4-Ethynylbenzonitrile)

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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-乙炔基苯甲腈 在 5,10,15-tris(pentafluorophenyl)corrole cobalt(III) triphenyl phosphine 、 硫酸 、 水 作用下， 以 甲醇 为溶剂， 反应 108.0h， 以92%的产率得到对氰基苯乙酮
  参考文献：
  名称：

  钴配合物催化的末端炔水合反应。

  摘要：

  首先将钴（III）溶液用于末端炔烃的水合。炔烃水合以良好的产率至优异的产率进行，钴负载量为0.03至0.3mol％。可以耐受多种底物。特别地，该反应在克规模的实验中可以得到90％的产率。

  DOI：

  10.1016/j.tetlet.2020.152426
• 作为产物：
  描述：

  4-碘氰基苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 4-乙炔基苯甲腈
  参考文献：
  名称：

  苯乙烯硼酸和氧化还原活性酯的有机光催化自由基-极性交叉偶联

  摘要：

  我们报告了在有机光氧化还原催化下使用苯乙烯基硼酸和氧化还原活性酯进行自由基-极性交叉偶联反应的进展。该反应通过正式的极性不匹配的自由基加成进行。与现有工艺相比，有机光催化剂的使用使得电子穿梭添加剂的用量非常低，并加快了反应时间。探索了反应的范围，并证明了产品的实用性。

  DOI：

  10.1055/a-2179-6570
• 作为试剂：
  描述：

  2,2,6,6-四甲基哌啶氧化物 、 4-乙基联苯 在 噻吩-2-甲酸亚铜(I) 、 4-乙炔基苯甲腈 、 N-(tert-butyl)-N-fluoro-4-(trifluoromethyl)benzenesulfonamide 、 N-(2-((3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazol-2-yl)-3-(trifluoromethyl)phenyl)-2-(diphenylphosphanyl)benzamide 、 caesium carbonate 作用下， 以 氯苯 为溶剂， 以15%的产率得到1-(1-([1,1'-biphenyl]-4-yl)ethoxy)-2,2,6,6-tetramethylpiperidine
  参考文献：
  名称：

  铜催化的分子间对映选择性自由基氧化 C(sp3)-H/C(sp)-H 与合理设计的恶唑啉衍生的 N,N,P(O)-配体的交叉偶联。

  摘要：

  C(sp3 )-H 键与容易获得的末端炔烃的分子间不对称自由基氧化 C(sp3 )-C(sp) 交叉偶联是一种很有前景的方法来形成手性 C(sp3 )-C(sp) 键，因为高原子和阶梯经济，但仍未得到充分探索。在这里，我们报告了铜催化的（杂）苄基和（环）烯丙基 CH 键与末端炔烃的不对称 C(sp3 )-C(sp) 交叉偶联，该键具有高到优异的对映选择性。成功的关键是手性恶唑啉衍生的 N,N,P(O)-配体的合理设计，它不仅能耐受分子间氢原子提取 (HAA) 过程所需的强氧化条件，而且还能诱导具有挑战性的对映控制。直接获得一系列合成有用的手性苄基炔烃和 1,4-烯炔，

  DOI：

  10.1002/anie.202110233

文献信息

• 신규한 셀레늄 고리 화합물 및 이의 제조방법
  申请人：KNU-Industry Cooperation Foundation 강원대학교산학협력단(220040088571) BRN ▼221-82-10213

  公开号：KR102037409B1

  公开（公告）日：2019-10-28

  2개 이상의 질소와 셀레늄이 고리 원소를 이루는 방향족 고리 화합물인 반응물질 1과, 적어도 이중 결합 이상의 결합을 갖는 반응물질 2를 로듐 촉매 반응 하에 반응시키는 단계; 및 상기 반응에 따라 상기 2개 이상의 질소위치에 상기 이중 결합 이상의 결합을 갖는 원소가 고리 원소로 첨가되어 셀레늄 고리 화합물이 합성되는 단계를 포함하며, 상기 반응물질 1 이고, 상기 반응물질 2는 알카인, 알켄, 나이트릴, 다이엔 결합 중 어느 하나를 포함하는 화합물인 것을 특징으로 하는 셀레늄 고리 화합물 합성 방법이 제공된다. (상기 R1, R2는 각각 수소, 할로겐기, 탄소수 1 내지 10의 알킬기, 탄소수 1 내지 10의 알케닐기, 탄소수 1 내지 10의 알키닐기, 탄소수 6 내지 12의 치환되거나 치환되지 않은 아릴기, 치환되거나 치환되지 않은 탄소수 5 내지 12의 헤테로아릴기 및 탄소수 1 내지 10의 알킬옥시로 이루어진 군으로부터 선택된 어느 하나이며, 상기 R1과 R2는 서로 연결되어 융합고리를 형성될 수 있음)

  2个以上的氮和硒形成环元素的芳香环化合物的反应物质1，至少具有双键以上的键合的反应物质2在铑催化反应下反应的步骤；以及根据所述反应，在所述2个以上的氮位置上，具有双键以上的键合的元素被添加为环元素以合成硒环化合物的步骤，其中所述反应物质1，并且所述反应物质2是包含碱金属，烯烃，腈，二烯键中的任何一种的化合物的硒环化合物合成方法，其特征在于提供。 （其中R1，R2分别为氢，卤素，1到10个碳原子的烷基，1到10个碳原子的烯基，1到10个碳原子的烷基，6到12个被取代或未被取代的芳基，5到12个被取代或未被取代的杂环芳基和1到10个烷氧基中的任何一个，其中R1和R2可以相互连接以形成融合环）
• Discovery of Quinazolin-4(3<i>H</i>)-ones as NLRP3 Inflammasome Inhibitors: Computational Design, Metal-Free Synthesis, and in Vitro Biological Evaluation
  作者：Mohd Abdullaha、Shabber Mohammed、Mehboob Ali、Ajay Kumar、Ram A. Vishwakarma、Sandip B. Bharate

  DOI：10.1021/acs.joc.9b00138

  日期：2019.5.3

  NLRP3 inflammasome is an important therapeutic target for a number of human diseases. Herein, computationally designed series of quinazolin-4(3H)-ones were synthesized using iodine-catalyzed coupling of arylalkynes (or styrenes) with O-aminobenzamides. The key event in this transformation involves the oxidative cleavage of the C–C triple/double bond and the release of formaldehyde. The reaction relies

  NLRP3炎性小体是许多人类疾病的重要治疗靶标。本文中，使用碘催化的芳基炔烃（或苯乙烯）与O-氨基苯甲酰胺的偶联反应，合成了一系列计算设计的喹唑啉4（3 H）-1 。此转变的关键事件涉及C–C三键/双键的氧化裂解和甲醛的释放。该反应取决于在无金属条件下C–N键的形成以及C–C键的裂解。硝基取代的喹唑啉-4（3 H）-1 2k通过抑制从ATP刺激的J774A.1细胞中释放的IL-1β抑制NLRP3炎性小体（IC 50 5μM）。
• Copper Promoted Regio- and Stereoselective Aminochlorination of Alkynes and Alkenes with NFSI
  作者：Weilin Wang、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1002/chem.201801262

  日期：2018.6.18

  aminochlorination of unactivated alkynes and alkenes with N‐fluorobenzenesulfonimide (NFSI) was developed. Two series of chloroenamines and chloroamines were obtained in good to high yields. The chlorinated enamines could be obtained in a single E configuration. This reaction involved a radical process and the CuCl2 acted as the Cl source and NFSI as the N source.

  开发了一种简单快速的用N-氟代苯磺酰亚胺（NFSI）对未活化的炔烃和烯烃进行铜促进的氨基氯化的方法。获得了高至高收率的两个系列的氯烯胺和氯胺。氯化烯胺可以以单一的E 构型获得。该反应涉及自由基过程，CuCl 2充当Cl源，NFSI充当N源。
• Catalytic Electrophilic Thiocarbocyclization of Allenes
  作者：Quanbin Jiang、Huimin Li、Xiaodan Zhao

  DOI：10.1021/acs.orglett.1c03270

  日期：2021.11.19

  An efficient approach via catalytic electrophilic thiocarbocyclization of allenes to construct indene-based sulfides with excellent regioselectivities is disclosed. The reactions were carried out at low temperatures by selenide catalysis in the presence of TMSOTf. Not only electrophilic arylthio reagents but also electrophilic alkylthio reagents worked well under these conditions. Furthermore, the

  公开了一种通过丙二烯的催化亲电硫代碳环化来构建具有优异区域选择性的茚基硫化物的有效方法。反应在低温下通过硒化物催化在 TMSOTf 存在下进行。在这些条件下，不仅亲电的芳硫基试剂而且亲电的烷硫基试剂都能很好地工作。此外，该方法可应用于丙二烯的分子间叠氮硫基化反应。
• Metal-free One-pot Synthesis of 1,2,4-Triazolo[4,3-<i>a</i>]pyridines from 2-Hydrazinylpyridines
  作者：L. Madhava Reddy、V. Veerabadra Reddy、P. Sai Prathima、Ch. Krishna Reddy、B. V. Subba Reddy

  DOI：10.1002/adsc.201800512

  日期：2018.8.17

  A metal‐free one‐pot strategy has been developed for the synthesis of 3‐aryl[1,2,4]triazolo[4,3‐a]pyridines through an oxidative cyclization of 2‐(2‐arylidenehydrazinyl)pyridines by utilizing molecular iodine in DMSO. This is the first report on the synthesis of 3‐aroyl[1,2,4]triazolo[4,3‐a]pyridines directly from α‐aryl methyl ketones or ethyl benzoylacetate or styrenes or phenylacetylenes and 2‐hydrazinylpyridines

  已开发出一种无金属的单锅策略，该方法通过利用分子间的2-（2-亚芳基肼基嗪）吡啶的氧化环化反应来合成3-芳基[1,2,4]三唑并[4,3- a ]吡啶DMSO中的碘。这是第一个关于直接由α-芳基甲基酮或苯甲酰乙酸乙酯或苯乙烯或苯乙炔和2-羟基苯并吡啶经碘促进的氧化法合成3-芳基[1,2,4]三唑并[4,3- a ]吡啶的报告。环化。碘的催化使用使该方法相当简单，更加方便和经济。而且，该方案在温和的反应条件下显示了较宽的底物范围，可以取代危险金属试剂的使用。

表征谱图