4-苄氨基吡啶 | 13556-71-3

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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-苄氨基吡啶
• 中文别名: 4-苄基氨基吡啶；4-N-苄基-氨基吡啶
• 英文名称: N-benzyl-4-aminopyridine
• 英文别名: N-benzylpyridin-4-amine；4-(Benzylamino)pyridine；N-benzyl-(4-pyridyl)amine
• CAS: 13556-71-3
• 化学式: C₁₂H₁₂N₂
• mdl: MFCD00466069
• 分子量: 184.241
• InChiKey: LCUREJHJUJCKQS-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109.5 °C
• 沸点：
  330.8±17.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Benzylaminopyridine
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-Benzylaminopyridine
CAS number: 13556-71-3

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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: C12H12N2
Molecular weight: 184.2

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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-苄氨基吡啶 在 ammonium formate 、 锌 作用下， 以 乙二醇 为溶剂， 反应 0.04h， 以95%的产率得到4-氨基吡啶
  参考文献：
  名称：

  Conventional and Microwave Assisted Hydrogenolysis Using Zinc and Ammonium Formate

  摘要：

  The selective deprotection of several N-Bzl amino derivatives to the corresponding amines and the removal of S-Bzl and O-Bzl groups from the protected amino acids with ammonium formate and commercial zinc dust are reported. Many other reducible or hydrogenolysable substituents such as halogens, methoxy, phenol, ester, acid, ethene, and Boc groups are unaffected.

  DOI：

  10.1081/scc-120034165
• 作为产物：
  描述：

  benzylidene-pyridin-4-yl-amine 在 polymethylhydrosiloxane 作用下， 以 二氯甲烷 为溶剂， 生成 4-苄氨基吡啶
  参考文献：
  名称：

  Polymethylhydrosiloxane (PMHS)/trifluoroacetic acid (TFA): a novel system for reductive amination reactions

  摘要：

  Polymethylhydrosiloxine (PMHS)/trifluoroacetic acid (TFA) was discovered as a novel metal-free system for reductive amination reactions. A variety of(het)aryl amines as well as a representative carbamate and urea were successfully alkylated by benzaldehyde in the presence of PMHS and TFA in dichloromethane at room temperature in moderate to excellent yields (28-87%). Furthermore, this reaction protocol was Successfully applied to the alkylation of p-nitroaniline with a wide range of aldehydes, ketones, and a representative acetal to obtain the alkylated products in yields ranging from 40% to 92%. The current work represents one of the very few examples of PMHS being activated by a Bronsted acid. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.048

文献信息

• Biorenewable carbon-supported Ru catalyst for <i>N</i>-alkylation of amines with alcohols and selective hydrogenation of nitroarenes
  作者：Vishakha Goyal、Naina Sarki、Mukesh Kumar Poddar、Anand Narani、Deependra Tripathi、Anjan Ray、Kishore Natte

  DOI：10.1039/d1nj01654g

  日期：——

  prepared via simple impregnation followed by the pyrolysis process. The prepared Ru/PNC-700 catalyst demonstrated remarkable catalytic activity in terms of conversion and selectivity towards N-alkylation of anilines with benzyl alcohol and chemoselective hydrogenation of aromatic nitro compounds. In addition, local anesthetic pharmaceutical agents (e.g., butamben and benzocaine), including key drug intermediates

  在此，我们开发了一种可再生的碳负载 Ru 催化剂（Ru/PNC-700），该催化剂通过简单的浸渍和热解过程轻松制备。制备的 Ru/PNC-700 催化剂在苯胺与苯甲醇的N-烷基化和芳香硝基化合物的化学选择性加氢的转化率和选择性方面表现出显着的催化活性。此外，局部麻醉药剂（例如、丁苯苯和苯佐卡因），包括关键的药物中间体，在温和的条件下和作为绿色溶剂的水的存在下以优异的产率合成。此外，制备的 Ru/PNC-700 催化剂可以很容易地回收和重复使用多达 5 次，而没有任何明显的活性和选择性损失。
• N-Alkylation of poor nucleophilic amine and sulfonamide derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate
  作者：Ana Martínez-Asencio、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tetlet.2009.11.009

  日期：2010.1

  Copper(II) acetate is a versatile, cheap, and simple catalyst for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines as well as sulfonamides, using in all cases primary alcohols as initial source of the electrophiles, through a hydrogen autotransfer process. In the case of sulfonamides, the monoalkylation process followed

  乙酸铜（II）是一种通用，廉价且简单的催化剂，用于在所有情况下均使用伯醇作为苯酚的初始来源，以对具有不良亲核特性的氨基衍生物（例如芳族和杂芳族胺以及磺酰胺）进行选择性N-单烷基化。亲核试剂，通过氢自动转移过程。在磺酰胺的情况下，单烷基化过程随后是萘催化的还原性脱保护得到伯胺，这是氨直接单烷基化的间接替代方法。
• Palladium-Catalyzed<i>N-</i>Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology
  作者：Xiaochun Yu、Lan Jiang、Qiang Li、Yuanyuan Xie、Qing Xu

  DOI：10.1002/cjoc.201200462

  日期：2012.10

  reactions of amines/amides with alcohols in the past. By employing the aerobic relay race methodology with Pd‐catalyzed aerobic alcohol oxidation being a more effective protocol for alcohol activation, ligand‐free homogeneous palladiums are successfully used as active catalysts in the dehydrative N‐alkylation reactions, giving high yields and selectivities of the alkylated amides and amines. Mechanistic

  可能是因为均相钯催化剂不是典型的借用氢催化剂，因此配体在常规厌氧条件下不能有效活化催化剂，因此过去从未将其用于胺/酰胺与醇的N-烷基化反应中。通过采用好氧接力竞赛方法，并以Pd催化的好氧醇氧化作为更有效的醇活化方案，无配体的均相钯已成功地用作脱水N-烷基化反应中的活性催化剂，从而提供了高收率和高选择性的烷基化酰胺和胺。机理研究表明，该反应很可能是通过我们最近发现并提出的新型中继竞争机制进行的。
• Selective N-monoalkylation of aromatic amines with benzylic alcohols by a hydrogen autotransfer process catalyzed by unmodified magnetite
  作者：Ricardo Martínez、Diego J. Ramón、Miguel Yus

  DOI：10.1039/b901929d

  日期：——

  A new catalyst for an old material: magnetite is a good catalyst for the selective N-alkylation of aromatic amines using benzylic alcohols as electrophiles. The process could be repeated up to eight times without losing effectiveness. The catalyst recycling is very easy, using a simple magnet. The catalyst is selective and could discriminate between aromatic and aliphatic amines, as well as between benzylic and aliphatic alcohols, as the reactions only take place with aromatic amines and benzylic alcohols.

  一种古老材料的全新催化剂：磁铁矿是一种优秀的催化剂，可以在使用苄醇作为亲电试剂的情况下选择性地对芳香胺进行N-烷基化。这个过程可以重复多达八次而不损失其效果。催化剂的回收非常简单，只需使用一块磁铁。该催化剂具有选择性，能够区分芳香胺和脂肪胺，以及苄醇和脂肪醇，因为反应仅在芳香胺和苄醇之间发生。
• Synthesis, characterization and catalytic activity of saturated and unsaturated N-heterocyclic carbene iridium(<scp>i</scp>) complexes
  作者：Yung-Hung Chang、Ching-Feng Fu、Yi-Hong Liu、Shei-Ming Peng、Jwu-Ting Chen、Shiuh-Tzung Liu

  DOI：10.1039/b814234c

  日期：——

  saturated and unsaturated N-benzyl substituted heterocyclic carbene (NHC) iridum(I) complexes were synthesized. The unsaturated carbene complex [(un-NHC-Bn)Ir(CO)2Cl] in the cis form was prepared via the carbene transfer from the corresponding silver complex to [Ir(COD)2Cl]2 followed by ligand substitution with CO, whereas the saturated complex was obtained via the transfer from (sat-NHC-Bn)W(CO)5. The treatment

  饱和和不饱和的N-苄基取代的杂环卡宾（NHC）铱（I）配合物被合成。不饱和卡宾顺式制备[[un-NHC-Bn）Ir（CO）2 Cl]配合物，方法是卡宾从相应的银转移络合物的[Ir（COD）2 CL] 2，接着配体用CO取代，而饱和配合物是通过（sat-NHC-Bn）W（CO）5的转移获得的。的治疗膦类（NHC）Ir（CO）2 Cl配合物制得的产物具有膦 配体 反式的碳烯部分通过取代。X射线结构测定表明，在（un-NHC-Bn）Ir（CO）（PR 3）Cl和（un-NHC-Bn）Ir（CO）（PR 3）Cl中，Ir–C （卡宾）的距离基本相同。铱配合物[（NHC）Ir（CO）（PR 3）Cl]和Vaska's配合物的光谱和晶体结构数据分析在两种配合物中都显示出相似的对应数据，这表明所研究的NHC配体 和 膦类与Ir（I）金属中心具有相似的键合。在这项工作中研究的所有铱络合物都说明了它们对三价铬的催化活性。N-烷基化