3-氰基苯甲酸甲酯 | 13531-48-1

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 3-氰基苯甲酸甲酯
• 中文别名: 间氰基苯甲酸甲酯；3-氰甲基苯甲酸甲酯；甲基3-氰基苯甲酸
• 英文名称: methyl 3-cyanobenzoate
• CAS: 13531-48-1
• 化学式: C₉H₇NO₂
• mdl: MFCD00220156
• 分子量: 161.16
• InChiKey: XPBHWSMZTSSEJE-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  267.2±23.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• LogP：
  1.82

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 海关编码：
  2926909090
• 安全说明：
  S22,S26,S36/37/39
• 储存条件：
  室温且干燥环境中使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Methyl 3-cyanobenzoate
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: Methyl 3-cyanobenzoate
CAS number: 13531-48-1

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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: C9H7NO2
Molecular weight: 161.2

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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：

  3-氰基苯甲酸甲酯 在 lithium hydroxide monohydrate 、 羟胺 、 silver(I) acetate 、 palladium diacetate 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 2.08h， 生成 3-[5-(2-氟苯基)-1,2,4-恶二唑-3-基]苯甲酸
  参考文献：
  名称：

  微波辐照下3-取代的1,2,4-恶二唑的钯催化银辅助C-5–H直接芳基化

  摘要：

  据报道，在钯催化剂和乙酸银存在下，3-取代的1,2,4-恶二唑与碘代芳烃的直接C-5-H芳基化反应。该方法提供了一种快速，可靠的方法来获得通用的3,5-二芳基-1,2,4-恶二唑衍生物，这是许多生物活性分子的常见部分。这种新方法的合成应用已在Ataluren和有效的RET抑制剂Yhhu251的简明合成中得到了证明。

  DOI：

  10.1002/adsc.201600913
• 作为产物：
  描述：

  3-(氯羰基)苯甲酸甲酯 在 磷酸酐 、 ammonium hydroxide 作用下， 生成 3-氰基苯甲酸甲酯
  参考文献：
  名称：

  Synthesis and properties of some novel anti-calmodulin drugs

  摘要：

  The preparation and properties of some novel inhibitors of calmodulin function are described. The compounds are cationic derivatives of phenyl-substituted thiazoles which inhibit the calmodulin stimulation of cyclic-AMP phosphodiesterase and are active against animal tumor cells in culture. These derivatives form the basis for the preparation of new, more potent inhibitors of calmodulin function which could take advantage of the reported elevated levels of calcium-bound calmodulin in tumor cells and show preferential anti-tumor activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00092-9

文献信息

• Cleavage of Carboxylic Esters by Aluminum and Iodine
  作者：Dayong Sang、Huaxin Yue、Yang Fu、Juan Tian

  DOI：10.1021/acs.joc.1c00034

  日期：2021.3.5

  A one-pot procedure for deprotecting carboxylic esters under nonhydrolytic conditions is described. Typical alkyl carboxylates are readily deblocked to the carboxylic acids by the action of aluminum powder and iodine in anhydrous acetonitrile. Cleavage of lactones affords the corresponding ω-iodoalkylcarboxylic acids. Aryl acetylates undergo deacetylation with the participation of the neighboring group

  描述了一种在非水解条件下使羧酸酯脱保护的一锅法方法。在无水乙腈中，铝粉和碘的作用下，典型的羧酸烷基酯很容易解封为羧酸。切割内酯得到相应的ω-碘代烷基羧酸。乙酸芳基酯在相邻基团的参与下进行脱乙酰化。该方法能够在芳基酯存在下选择性裂解烷基羧酸酯。
• Microbial hydrolysis as a potent method for the preparation of optically active nitriles, amides and carboxylic acids
  作者：Hideaki Kakeya、Naoko Sakai、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1016/s0040-4039(00)79663-8

  日期：1991.3

  Many kinds of aromatic nitriles have been hydrolyzed to afford the corresponding amides and carboxylic acids, by the aid of enzyme system of Rhodococcus butanica. This enzymatic hydrolysis can be successfully applied to the kinetic resolution of α-arylpropionitriles, resulting in the formation of (R)-amides and (S)-carboxylic acids.

  借助于丁酸红球菌的酶系统，已经将多种芳族腈水解成相应的酰胺和羧酸。该酶促水解可成功地应用于α-芳基丙腈的动力学拆分，从而导致形成（R）-酰胺和（S）-羧酸。
• A Mild and Efficient Palladium-Catalyzed Cyanation of Aryl Mesylates in Water or tBuOH/Water
  作者：Pui Yee Yeung、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/anie.201005121

  日期：2010.11.15

  Cool and compatible: Aryl mesylates and tosylates underwent palladium‐catalyzed cyanation under mild, aqueous conditions at 65–80 °C (see scheme). In many cases, water could be used as the reaction medium without a cosolvent, and a variety of substituents R, such as keto, aldehyde, ester, free amine, and nitrile groups, remained intact during the transformation. Cy=cyclohexyl, Ms=methanesulfonyl,

  凉爽且相容：芳基甲磺酸酯和甲苯磺酸酯在65-80°C的温和水溶液条件下经历了钯催化的氰化反应（请参见方案）。在许多情况下，可以将水用作没有助溶剂的反应介质，并且在转化过程中，各种取代基R（例如酮，醛，酯，游离胺和腈基）保持完整。Cy =环己基，Ms =甲磺酰基，Ts =对甲苯磺酰基。
• The First Example for Cyanation of Arylboronic Acids with Nontoxic and Inexpensive K₄[Fe(CN)₆]
  作者：Xinzhe Tian、Yanpei Sun、Chuanhua Dong、Kaixuan Zhang、Tengfei Liang、Yu Zhang、Chaodong Hou

  DOI：10.1246/cl.2012.719

  日期：2012.7.5

  Nontoxic and inexpensive K4[Fe(CN)6] is first introduced as a cyanating agent to cyanation of arylboronic acids. The present method is simple, practical, and allowed a wide range of substrates including functionalized phenylboronic acids, 1-naphthylboronic acid as well as heterocyclic boronic acids to be smoothly converted into the corresponding products in moderate to high yields.

  首先介绍无毒且廉价的K4[Fe(CN)6]作为氰化剂，用于芳基硼酸的氰化反应。本方法简单、实用，允许包括功能化苯硼酸、1-萘硼酸以及杂环硼酸在内的广泛底物顺利转化为其相应产物，产率中等到高。
• Pd‐Colloids‐Catalyzed/Ag ₂ O‐Oxidized General and Selective Esterification of Benzylic Alcohols
  作者：Vaibhav Sable、Jagrut Shah、Anuja Sharma、Anant R. Kapdi

  DOI：10.1002/asia.201900566

  日期：2019.8

  Palladium colloids obtained from the degradation of Hermann–Beller palladacycle proved to be an efficient catalytic system in combination with silver oxide as a selective oxidant for the oxidative esterification of differently substituted benzyl alcohols in MeOH as solvent. Excellent reactivity exhibited by the catalytic system also allowed the alcoholic coupling partner to be changed from MeOH to

  从Hermann-Beller palladacycle的降解中获得的钯胶体被证明是一种有效的催化体系，与氧化银作为选择性氧化剂结合使用，可在甲醇为溶剂的情况下对不同取代的苄醇进行氧化酯化。催化体系表现出的优异的反应性也使醇类偶合体从MeOH转变为具有各种功能的多种醇类。所开发方案的温和性还使得可以使用炔丙醇作为偶联伴侣，而没有观察到末端炔烃的任何干扰。使用开发的催化剂体系，在乙二醇和甘油的情况下，伯醇官能团相对于仲醇的选择性氧化偶联也是可能的。

表征谱图