(4-氯苯基)-氧代乙腈 | 13014-48-7

• 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: (4-氯苯基)-氧代乙腈
• 英文名称: 4-chlorobenzoyl cyanide
• 英文别名: p-chlorobenzoyl cyanide
• CAS: 13014-48-7
• 化学式: C₈H₄ClNO
• mdl: MFCD06658396
• 分子量: 165.579
• InChiKey: UDBBCXDMJVNFLI-UHFFFAOYSA-N

物化性质

• 熔点：
  41-42.5 °C
• 沸点：
  120-122 °C(Press: 24 Torr)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 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：
  40.9
• 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-Chloro-phenyl)-oxo-acetonitrile
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-Chloro-phenyl)-oxo-acetonitrile
CAS number: 13014-48-7

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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: C8H4ClNO
Molecular weight: 165.6

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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-氯苯基)-氧代乙腈 在 四(三苯基膦)钯 作用下， 以 苯 为溶剂， 反应 12.0h， 以98%的产率得到对氯苯甲腈
  参考文献：
  名称：

  Palladium-catalyzed decarbonylation of acyl cyanides

  摘要：

  DOI：

  10.1021/jo00356a029
• 作为产物：
  描述：

  (+/-)-2-(4-chlorophenyl)-2-(trimethylsiloxy)-acetonitrile 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以93%的产率得到(4-氯苯基)-氧代乙腈
  参考文献：
  名称：

  Haerle, Helmut; Jochims, Johannes C., Chemische Berichte, 1986, vol. 119, # 4, p. 1400 - 1412

  摘要：

  DOI：

文献信息

• Synthesis of benzoyl cyanide through aerobic photooxidation of benzyl cyanide using carbon tetrabromide as a catalyst
  作者：Y. Sugiura、Y. Tachikawa、Y. Nagasawa、N. Tada、A. Itoh

  DOI：10.1039/c5ra13269j

  日期：——

  We developed a synthetic method toward benzoyl cyanide through aerobic photooxidation of benzyl cyanide in the presence of carbon tetrabromide under visible light irradiation with fluorescent lamps.

  我们开发了一种合成方法，该方法通过在可见光照射下用荧光灯在四溴化碳存在下，通过苄基氰的需氧光氧化来对苯甲酰氰进行合成。
• Structure–reactivity correlations in nucleophilic substitution reactions of Y-substituted phenyl X-substituted benzoates with anionic and neutral nucleophiles
  作者：Ik-Hwan Um、Ji-Youn Lee、Mizue Fujio、Yuho Tsuno

  DOI：10.1039/b607194e

  日期：——

  A kinetic study is reported for the reactions of 4-nitrophenyl X-substituted benzoates (1a-1) and Y-substituted phenyl benzoates (2a-1) with two anionic nucleophiles (OH(-) and CN(-)) and three amines (piperidine, hydrazine, and glycylglycine) in 80 mol% H(2)O-20 mol% dimethyl sulfoxide (DMSO) at 25.0 +/- 0.1 degrees C. Each Hammett plot exhibits two intersecting straight lines for the reactions of

  动力学研究报道了4-硝基苯基X-取代的苯甲酸酯（1a-1）和Y-取代的苯基苯甲酸酯（2a-1）与两个阴离子亲核试剂（OH（-）和CN（-））和三种胺的反应（哌啶，肼和甘氨酰甘氨酸）在25.0 +/- 0.1摄氏度下于80 mol％H（2）O-20 mol％二甲基亚砜（DMSO）中的溶液。每个Hammett曲线对于1a-1反应显示两条相交的直线阴离子亲核试剂和哌啶，而相同反应的Yukawa-Tsuno图是线性的。2a-1与肼和甘氨酰甘氨酸反应的Hammett图显示，与sigma（-）常数的线性相关性比与sigma度或sigma常数的线性相关性好得多，这表明离去基团的离去发生在速率确定步骤（RDS）。相反，与相应的与OH（-）和CN（-）的反应相比，sigma（-）常数导致的Hammett相关性比sigma度常数差，这表明离去基团的离去发生在RDS之后与阴离子亲核试剂的反应。1a-1与阴离子亲核试剂反应获得的较大的rh（X）值（1
• Proline-catalyzed aldol reactions of acyl cyanides with acetone: an efficient and convenient synthesis of 1,3-diketones
  作者：Zongxuan Shen、Bin Li、Lu Wang、Yawen Zhang

  DOI：10.1016/j.tetlet.2005.10.036

  日期：2005.12

  The aldol-type addition of acetone towards (un)substituted benzoyl, heteroarylcarbonyl or α,β-unsaturated acyl cyanides was efficiently catalyzed by l-proline (30 mol %) to give 2-hydroxy-4-oxo-2-substituted pentanenitriles. Upon the treatment with sodium hydroxide, the adducts transformed to 1,3-diketones in good-to-excellent yield, furnishing an efficient and convenient method for the regioselective

  丙酮对（未）取代的苯甲酰基，杂芳基羰基或α，β-不饱和酰基氰的醛醇型加成被1-脯氨酸（30mol％）有效地催化，得到2-羟基-4-氧代-2-取代的戊腈。用氢氧化钠处理后，加合物以良好至优异的产率转化为1，3-二酮，为1，3-二酮的区域选择性合成提供了一种有效而方便的方法。
• Glyt1 Transporter Inhibitors and Uses Thereof in Treatment of Neurological and Neuropsychiatric Disorders
  申请人：Dean Anthony William

  公开号：US20080221185A1

  公开（公告）日：2008-09-11

  The invention provides a compound of formula (I) or a solvate thereof: wherein R 1 , R 2 , R 3, R 4 , R 5 , R 6 , and n are as defined in the specification, and uses of such compounds. The compounds inhibit GlyT1 transporters and are useful in the treatment of certain neurological and neuropsychiatric disorders, including schizophrenia.

  该发明提供了化合物的结构式(I)或其溶剂化物：其中R1、R2、R3、R4、R5、R6和n如规范中所定义，并且这些化合物的用途。这些化合物抑制GlyT1转运体，在治疗某些神经系统和神经精神疾病，包括精神分裂症方面具有用处。
• A Convenient and Improved Method for the Preparation of Cyanohydrin Esters from Acyl Cyanides and Aldehydes
  作者：Mitsuhiro Okimoto、Toshiro Chiba

  DOI：10.1055/s-1996-4361

  日期：1996.10

  Various kinds of cyanohydrin esters can be obtained in good to excellent yields from aldehydes by treatment with acyl cyanides in a heterogeneous mixture of aqueous potassium carbonate and acetonitrile.

  通过在水性碳酸钾和乙腈的异相混合物中用酰基氰化物处理醛，可以获得多种氰醇酯，收率良好至优异。

表征谱图