对氰基苄胺 | 10406-25-4

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 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: 对氰基苄胺
• 中文别名: 4-氰基苯甲胺；4-氰基苄胺；4-氰基苄胺盐酸盐；4-(氨基甲基)苯腈；4-氨甲基苯腈
• 英文名称: 4-aminobenzyl cyanide
• 英文别名: 4-cyanobenzylamine；4-(aminomethyl)benzonitrile；p-cyanobenzylamine
• CAS: 10406-25-4
• 化学式: C₈H₈N₂
• mdl: MFCD00025578
• 分子量: 132.165
• InChiKey: LFIWXXXFJFOECP-UHFFFAOYSA-N

物化性质

• 熔点：
  274-279 °C(lit.)
• 沸点：
  92 °C(Press: 5 Torr)
• 密度：
  1.1
• pKa：
  8.47±0.10 (Predicted,Most Basic Temp: 25 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  TOXIC
• 危险品标志：
  T
• 安全说明：
  S22,S24/25
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2926909090
• 储存条件：
  存储条件：2-8°C，避光保存，并置于惰性气体环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Cyanobenzylamine
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-Cyanobenzylamine
CAS number: 10406-25-4

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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: C8H8N2
Molecular weight: 132.2

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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

制备方法与用途

用途：用于有机合成、液晶高分子合成以及医药中间体的制备。

反应信息

• 作为反应物：
  描述：

  对氰基苄胺 在 N-氯代丁二酰亚胺 、 三乙胺 作用下， 反应 0.5h， 生成 对苯二腈
  参考文献：
  名称：

  胺的机械化学辅助氧化成羰基化合物和腈

  摘要：

  介绍了一种在球磨条件下将伯胺温和、高效、无金属和无溶剂氧化成醛、酮和腈的方法。该方法已被证明与各种官能团兼容，并且需要易于获得的起始材料。通过硅胶垫简单过滤反应混合物，得到纯醛、酮和腈产物。

  DOI：

  10.1002/ejoc.201700689
• 作为产物：
  描述：

  对苯二腈 在 二氧化碳 、 Rh/Al₂O₃ 、 氢气 作用下， 反应 6.0h， 以94.2%的产率得到对氰基苄胺
  参考文献：
  名称：

  在超临界二氧化碳中由二硝基苯到二甲腈的高效加氢

  摘要：

  己二腈的高选择性加氢在超临界二氧化碳（scCO 2）中有效地进行，以生成6-氨基己腈，相对于铑/氧化铝（Rh / Al 2 O 3）具有100％的优异选择性，并且没有任何添加剂，这在传统有机溶剂中是不可能的溶剂。CO 2的存在对于氨基腈的排他形成可能是有益的或强制性的，因为它可以充当溶剂来增强活性，也可以作为临时保护剂来提高选择性。这些结果成功显示了使用scCO 2的一般概念作为选择性控制二腈对氨基腈反应的保护性介质。还研究了催化剂的再循环以及该方法进一步扩展到其他二腈的方法。

  DOI：

  10.1002/adsc.201000514
• 作为试剂：
  描述：

  8-(benzyloxy)-5-hydroxy-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one 、 三乙胺 在 ice 、 对氰基苄胺 、 三乙胺 、 1,4-二氧六环 、 silica gel 、 chloroform methanol 作用下， 以 二氯甲烷 、 三氟甲磺酸酐 为溶剂， 反应 7.33h， 以to obtain a yellow solid of 4-(((8-(benzyloxy)-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-5-yl)amino)methyl)benzonitrile (57 mg)的产率得到4-(((8-(benzyloxy)-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-5-yl)amino)methyl)benzonitrile
  参考文献：
  名称：

  HETEROCYCLIC COMPOUND HAVING ANTI-HIV ACTIVITY

  摘要：

  一种由通式表示的杂环化合物（在该式中，R1、R2和R3可以相同也可以不同，每个代表氢原子、卤素原子或这种通式（X1-Y1-R4）（在该式中：X1代表这种通式（NR5）（在该式中，R5代表氢原子等）或类似物；Y1代表可选取代的C1-6烷基链或类似物；R4代表可选取代的芳基或类似物），且Z代表氮原子或这种通式（CR6）（在该式中，R6代表氢原子、卤素原子或可选取代的C1-12烷基链或类似物））或其盐，表现出优异的抗HIV活性，可作为抗HIV药物。

  公开号：

  US20150018546A1

文献信息

• [EN] PYRAZOLOPYRIMIDINES AS CYCLIN-DEPENDENT KINASE INHIBITORS<br/>[FR] PYRAZOLOPYRIMIDINES TENANT LIEU D'INHIBITEURS DE KINASES DEPENDANTES DE LA CYCLINE
  申请人：SCHERING CORP

  公开号：WO2004022561A1

  公开（公告）日：2004-03-18

  In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.

  在其多种实施方式中，本发明提供了一类新型的吡唑并[1,5-a]嘧啶化合物，作为细胞周期依赖性激酶的抑制剂，以及制备这类化合物的方法，含有一种或多种这类化合物的药物组合物，制备包含一种或多种这类化合物的药物配方的方法，以及利用这类化合物或药物组合物治疗、预防、抑制或改善与CDKs相关的一种或多种疾病的方法。
• Copper-Catalyzed One-Pot Oxidation–Aldol/Henry Reaction of Benzylic ­Amines to α,β-Unsaturated Methyl Ketone/Nitro Compounds
  作者：Wei-Dong Chen、Bu-Bing Zeng、Jia Liu、Xiao-Rui Zhu、Jiangmeng Ren

  DOI：10.1055/s-0033-1338986

  日期：——

  of α,β-unsaturated methyl ketone/nitro compounds from benzylic amines through an oxidation–aldol/Henry reaction is reported. The reaction proceeded well by using MCPBA as oxidant and CuCl2·2H2O as catalyst. A variety of functionalized α,β-unsaturated methyl ketone/nitro compounds were assembled in moderate yields by application of this catalytic one-pot reaction.

  报道了一种通过氧化-羟醛/亨利反应从苄胺中合成 α,β-不饱和甲基酮/硝基化合物的新型一锅法。以MCPBA为氧化剂，CuCl2·2H2O为催化剂，反应进行得很好。通过应用这种催化一锅反应，以中等产率组装了各种功能化的α,β-不饱和甲基酮/硝基化合物。
• Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers
  作者：Tristan Delcaillau、Philip Boehm、Bill Morandi

  DOI：10.1021/jacs.1c00529

  日期：2021.3.17

  We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications

  我们描述了芳基腈和芳基硫醚之间的新官能团复分解。催化系统镍/dcype 对于实现这种完全可逆的转化，以良好的收率至关重要。此外，不含氰化物和硫醇的反应显示出高官能团耐受性和商业分子后期衍生化的高效率。最后，合成应用证明了它在多步合成中的多功能性和实用性。
• Discovery of Novel Pterostilbene-Based Derivatives as Potent and Orally Active NLRP3 Inflammasome Inhibitors with Inflammatory Activity for Colitis
  作者：Liu Zeng Chen、Xing Xing Zhang、Ming Ming Liu、Jing Wu、Duo Ma、Liang Zhuo Diao、Qingshan Li、Yan Shuang Huang、Rui Zhang、Ban Feng Ruan、Xin Hua Liu

  DOI：10.1021/acs.jmedchem.1c01007

  日期：2021.9.23

  Studies have shown that the abnormal activation of the NLRP3 inflammasome is involved in a variety of inflammatory-based diseases. In this study, a high content screening model targeting the activation of inflammasome was first established and pterostilbene was discovered as the active scaffold. Based on this finding, total of 50 pterostilbene derivatives were then designed and synthesized. Among them

  研究表明NLRP3炎症小体的异常激活与多种炎症性疾病有关。本研究首次建立了针对炎症小体激活的高内涵筛选模型，并发现紫檀芪作为活性支架。基于这一发现，设计并合成了总共50种紫檀芪衍生物。其中，化合物47被发现是抑制细胞焦亡最好的一种[抑制率(IR) = 73.09% at 10 μM]，表现出低毒高效[针对白细胞介素-1β(IL-1β)：半最大抑制浓度(IC 50 ) = 0.56 μM]。进一步的研究表明，化合物47通过靶向NLRP3影响NLRP3炎症小体的组装。体内生物活性表明，该化合物可显着减轻右旋糖酐硫酸钠（DSS）诱导的小鼠结肠炎。总的来说，我们的研究提供了一种直接靶向NLRP3蛋白的新型先导化合物，值得进一步研究和结构优化。
• Reaction Discovery by Using a Sandwich Immunoassay
  作者：Julia Quinton、Sergii Kolodych、Manon Chaumonet、Valentina Bevilacqua、Marie-Claire Nevers、Hervé Volland、Sandra Gabillet、Pierre Thuéry、Christophe Créminon、Frédéric Taran

  DOI：10.1002/anie.201201451

  日期：2012.6.18

  Mmm, a reaction sandwich…︁ Using an immunoassay‐based technique able to monitor any kind of cross‐coupling reaction, a systematic and rapid evaluation of a large panel of random reactions was carried out. This approach led to the discovery of two new copper‐promoted reactions: a desulfurization reaction of thioureas leading to isoureas and a cyclization reaction leading to thiazole derivatives from

  嗯，反应夹心……︁使用基于免疫分析的技术能够监测任何种类的交叉偶联反应，对大量随机反应进行了系统，快速的评估。这种方法导致发现了两个新的铜促进的反应：硫脲的脱硫反应导致异脲，环化反应导致炔烃和N-羟基硫脲的噻唑衍生物。

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