4-氰基-N,N-二甲基苯胺 | 24167-50-8

• 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-氰基-N,N-二甲基苯胺
• 英文名称: N,N-dimethyl-4-cyanobenzamide
• 英文别名: 4-cyano-N,N-dimethylbenzamide；N,N-Dimethyl-p-cyanbenzamid；p-Cyano-N,N-dimethylbenzamid
• CAS: 24167-50-8
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD07186293
• 分子量: 174.202
• InChiKey: CPSNYKXHMCDALW-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P264,P270,P301+P312,P330,P302+P352,P333+P313,P321,P261,P272,P280,P363,P501
• 危险性描述：
  H302,H317
• 储存条件：
  存储条件：2-8°C，干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Cyano-N,N-dimethylbenzamide
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-Cyano-N,N-dimethylbenzamide
CAS number: 24167-50-8

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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: C10H10N2O
Molecular weight: 174.2

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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-氰基-N,N-二甲基苯胺 在 高氯酸四乙基铵 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以70%的产率得到N,N-二甲基苯甲酰胺
  参考文献：
  名称：

  A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

  摘要：

  描述了一种使用三乙胺作为牺牲还原剂的简便电还原去功能化系统，通过简单地改变反应溶剂，可以方便地切换还原的选择性和能力。

  DOI：

  10.1039/d1gc00317h
• 作为产物：
  描述：

  对氰基苯甲酸 在 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-氰基-N,N-二甲基苯胺
  参考文献：
  名称：

  通过酰胺-酰碘重路由的亲电 N-C(O) 活化对未活化叔酰胺进行高化学选择性转酰胺化

  摘要：

  使用等量的胺对未活化的叔酰胺进行具有挑战性的转酰胺化反应是通过协同酸/碘化物催化完成的。该方法提供了一种新的方法，通过反应性酰碘中间体重新引导未活化和未反应性N,N-二烷基酰胺的反应性，代表了一种强大的未活化酰胺键的新活化模式。

  DOI：

  10.1002/anie.202202794

文献信息

• Copper catalyzed cross-coupling reactions of carboxylic acids: an expedient route to amides, 5-substituted γ-lactams and α-acyloxy esters
  作者：S. Priyadarshini、P. J. Amal Joseph、M. Lakshmi Kantam

  DOI：10.1039/c3ra41000e

  日期：——

  A convenient and recyclable catalytic protocol for the synthesis of N,N-dimethyl substituted amides, 5-substituted γ-lactams and α-acyloxy ethers from carboxylic acids using CuO nanoparticles and TBHP is described.

  描述了使用CuO纳米颗粒和TBHP从羧酸合成N，N-二甲基取代的酰胺，5-取代的γ-内酰胺和α-酰氧基醚的方便且可回收的催化方案。
• Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application
  作者：Bo Han、Jiong Zhang、Haijun Jiao、Lipeng Wu

  DOI：10.1016/s1872-2067(21)63853-6

  日期：2021.11

  diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

  开发用于选择性合成胺的温和高效的催化方法是一个长期的研究目标。在这方面，催化脱氧酰胺还原已被证明是有前途但具有挑战性的，因为这种方法需要选择性的 C-O 键裂解。在此，我们报告了伯、仲和叔酰胺在室温下由地球丰富的金属催化剂 Zr-H 催化的选择性硼氢化反应，以获取不同的胺。各种易于还原的官能团，如酯、炔烃和烯烃，都具有良好的耐受性。此外，该方法还扩展到生物和药物衍生胺的合成。详细的机理研究揭示了一个反应途径，通过一个不寻常的 C-N 键断裂-重整过程形成醛和酰胺复合物，然后是 C-O 键断裂。
• Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
  作者：L. Reginald Mills、Joshua M. Graham、Purvish Patel、Sophie A. L. Rousseaux

  DOI：10.1021/jacs.9b11208

  日期：2019.12.11

  reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for

  在此，我们报告了一种 Ni 催化的还原偶联，用于从芳基（伪）卤化物和亲电氰化试剂 2-甲基-2-苯基丙二腈 (MPMN) 合成苯甲腈。MPMN 是一种工作台稳定的碳键合亲电子 CN 试剂，在反应条件下不会释放氰化物。可以以良好的收率制备多种与药用相关的苯甲腈。将 NaBr 添加到反应混合物中可以使用更具挑战性的芳基亲电试剂，例如芳基氯化物、甲苯磺酸盐和三氟甲磺酸盐。机理研究表明，溴化钠在促进这些底物的氧化加成方面发挥作用。
• Highly Efficient Gold Nanoparticle Catalyzed Deoxygenation of Amides, Sulfoxides, and Pyridine N-Oxides
  作者：Yusuke Mikami、Akifumi Noujima、Takato Mitsudome、Tomoo Mizugaki、Koichiro Jitsukawa、Kiyotomi Kaneda

  DOI：10.1002/chem.201003109

  日期：2011.2.7

  HAPpy catalysts: Hydroxyapatite‐supported gold nanoparticles efficiently catalyze the deoxygenation of amides, sulfoxides, and pyridine N‐oxides, with silanes as reductants, to give the corresponding products with excellent turnover numbers (see graphic). Furthermore, this catalyst is easily recovered and reused without any loss of efficiency.

  HAPpy催化剂：以羟基磷灰石为载体的金纳米颗粒，以硅烷为还原剂，可有效催化酰胺，亚砜和吡啶N-氧化物的脱氧反应，从而制得具有优异周转率的相应产品（见图）。此外，该催化剂易于回收和再利用而没有任何效率损失。
• 一种酰胺化合物还原制备胺类化合物的方法
  申请人：中国科学院兰州化学物理研究所

  公开号：CN112299938A

  公开（公告）日：2021-02-02

  本发明涉及一种酰胺化合物还原制备胺类化合物的方法，该方法是指在保护气氛中，将酰胺类化合物或环状酰胺、锆金属催化剂、频哪醇硼烷混合，于室温条件下进行酰胺还原反应，12~48h后通过氯化氢的乙醚溶液后处理，即得胺的盐酸盐化合物。本发明操作简单、成本低且具有良好的官能团耐受性和广泛的底物范围。

表征谱图