4-(烯丙氧基)苯甲腈 | 33148-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-(烯丙氧基)苯甲腈
• 英文名称: 4-allyloxy-benzonitrile
• 英文别名: allyl 4-cyanophenyl ether；4-cyanophenyl allyl ether；1-(allyloxy)-4-cyanobenzene；4-(Allyloxy)benzonitrile；4-prop-2-enoxybenzonitrile
• CAS: 33148-47-9
• 化学式: C₁₀H₉NO
• mdl: MFCD09940590
• 分子量: 159.188
• InChiKey: NEFWHNGRRGVCEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

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-(Allyloxy)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-(Allyloxy)benzonitrile
CAS number: 33148-47-9

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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: C10H9NO
Molecular weight: 159.2

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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：

  4-(烯丙氧基)苯甲腈 在 cerium(III) chloride 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以98%的产率得到4-羟基苯甲腈
  参考文献：
  名称：

  通过加入CeCl烯丙基醚的有效和选择性脱保护3 ·7H 2 O的NaI系统

  摘要：

  描述了一种温和，新颖和化学选择性的方法，用于通过CeCl 3 .7H 2 O 3 NaI系统对烯丙基醚进行脱保护。

  DOI：

  10.1016/s0040-4039(99)01575-0
• 作为产物：
  描述：

  p-allyloxybenzaldehyde oxime 在 苯酐 作用下， 反应 0.08h， 以88%的产率得到4-(烯丙氧基)苯甲腈
  参考文献：
  名称：

  邻苯二甲酸酐脱水醛肟制备腈的有效方法

  摘要：

  建立了一种新的高效醛肟转化为腈的方法。通过与邻苯二甲酸酐的融合，醛肟以高产率（超过 85%）和在短时间内（5 分钟内）高效且顺利地转化为腈类。邻苯二甲酸酐、环状酸酐和融合态醛肟的混合物为酰化醛肟选择性[3.3]-σ迁移重排为腈建立了理想的过渡态。

  DOI：

  10.1002/jccs.200400093

文献信息

• Phase-Transfer Catalyzed Nucleophilic Addition of Arylalkanenitrile Carbanions to Substituted Propenylarenes
  作者：Wojciech Lasek、Mieczysław Makosza

  DOI：10.1055/s-1993-35865

  日期：——

  Phenylacetonitrile and 2-phenylalkanenitriles react under phase transfer catalysis conditions with 2-propenylanisoles containing electron-withdrawing substituents (or their corresponding precursors, 2-allylanisoles) via the Michael addition pathway to give substituted 4-aryl-2-phenylbutyronitriles.

  苯乙腈和2-苯基链烯腈在相转移催化条件下与含有吸电子取代基的2-丙烯基茴香醚（或其对应的预体，2-烯丙基茴香醚）通过迈克尔加成途径反应，生成取代的4-芳基-2-苯基丁腈。
• Practical one-pot conversion of aryl bromides and β-bromostyrenes into aromatic nitriles and cinnamonitriles
  作者：Genki Ishii、Ryo Harigae、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2012.12.022

  日期：2013.2

  reactions are practical and environmentally benign one-pot methods for the preparation of aromatic nitriles, cinnamonitriles, and aliphatic nitriles from aryl bromides, β-bromostyrenes, and alkyl bromides, respectively, through the formation of Grignard reagents and their DMF or N-formylpiperidine adducts.

  通过用Mg车削和随后的DMF处理，然后用分子碘和NH 3水溶液处理，各种芳基溴化物以良好的产率有效地转化为相应的芳族腈。相同的处理芳基溴化物，其是弱反应到Mg屑，与我PrMgCl·LiCl并随后DMF，接着用分子碘治疗和水溶液NH 3也得到相应的芳香腈以良好的收率。另一方面，当使用N-甲酰基哌啶代替DMF时，对位取代的β-溴苯乙烯被转化为相应的对位取代的肉桂腈，即α，β-不饱和腈，通过相同的方法具有良好至中等的收率。该反应通过简单的实验程序进行，不需要任何有毒的金属氰化物或昂贵的稀有金属。因此，本反应是实用的，对环境有益的一锅法，可通过形成格氏试剂及其DMF或DMF分别由芳基溴化物，β-溴苯乙烯和烷基溴化物制备芳族腈，肉桂腈和脂族​​腈。N-甲酰基哌啶加合物。
• Chemoselective Schmidt Reaction Mediated by Triflic Acid: Selective Synthesis of Nitriles from Aldehydes
  作者：Balaji V. Rokade、Kandikere Ramaiah Prabhu

  DOI：10.1021/jo3008258

  日期：2012.6.15

  An excellent utility of Schmidt reaction of aldehydes to access corresponding nitriles in an instantaneous reaction is demonstrated. The reaction of aldehydes with NaN3 and TfOH furnishes the corresponding nitriles in near quantitative yields and tolerates a variety of electron-withdrawing and electron-donating substituents on the substrates. Formanilides, a common side product in Schmidt reaction

  已证明醛的Schmidt反应在瞬时反应中能很好地利用相应的腈。醛与NaN 3和TfOH的反应以接近定量的产率提供了相应的腈，并且可以承受底物上的各种吸电子和供电子取代基。在施密特反应中常见的副产物甲虫胺未在该反应中观察到。除了这些优点之外，该反应的显着特征是它显示出显着的化学选择性，因为在反应条件下对酸和酮的官能度具有很好的耐受性。该反应易于扩展，高收率并且几乎是瞬时的。
• Palladium-Catalyzed Norbornene-Mediated Tandem <i>ortho</i>-C–H-Amination/<i>ipso</i>-C–I-Cyanation of Iodoarenes: Regiospecific Synthesis of 2-Aminobenzonitrile
  作者：Biju Majhi、Brindaban C. Ranu

  DOI：10.1021/acs.orglett.6b02113

  日期：2016.9.2

  Efficient tandem ortho-C–H-amination/ipso-cyanation of iodoarenes was accomplished under a norbornene-mediated Pd-catalyzed process. A series of functionalized 2-aminobenzonitriles with much potential in the pharmaceutical industry were obtained by this protocol. This strategy was successfully employed for substitution with two cyano and four amino functionalities in an arene unit in one step under

  高效串联邻-C-H-胺化/本位iodoarenes的-cyanation被降冰片烯-介导的Pd催化的过程下完成的。通过该方案获得了一系列在制药工业中具有巨大潜力的官能化的2-氨基苯甲腈。在指定条件下，这一策略已成功用于一步一步在芳烃单元中被两个氰基和四个氨基官能团取代。
• Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride
  作者：Shunsuke Chiba、Derek Yiren Ong

  DOI：10.1055/s-0039-1690838

  日期：2020.5

  new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder

  使用氢化钠和氯化锌的组合，开发了一种控制腈还原为醛的新方案。衍生自芳族腈的亚胺基锌中间体可以用烯丙基金属亲核试剂进一步官能化以提供高烯丙基胺。由于该方法可以在较温和的反应条件下以简明的方法还原各种脂族和芳族腈，并且具有广泛的官能团相容性，因此非常适合用于化学合成中的各种机会。