2-乙酰氨基-6-甲基嘧啶 | 5327-33-3

• 物质功能分类: 医药中间体 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-乙酰氨基-6-甲基嘧啶
• 中文别名: 2-乙酰胺-6-甲基吡啶；2-乙酰氨基-6-甲基吡啶
• 英文名称: 2-acetylamino-6-methylpyridine
• 英文别名: 2-Acetamido-6-methylpyridine；N-(6-methylpyridin-2-yl)acetamide
• CAS: 5327-33-3
• 化学式: C₈H₁₀N₂O
• mdl: MFCD00091881
• 分子量: 150.18
• InChiKey: UEXYAZLLFZIXHN-UHFFFAOYSA-N

物化性质

• 熔点：
  87.0 to 91.0 °C
• 沸点：
  321.6±22.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇
• 稳定性/保质期：

  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  避光，存于阴凉干燥处，并密封保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Acetamido-6-methylpyridine
Product Name:
Synonyms: N-(6-Methylpyridin-2-yl)acetamide, 2-acetamido-6-picoline

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Acetamido-6-methylpyridine
CAS number: 5327-33-3

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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
This product should be handled only by, or under the close supervision of, those properly qualified
Handling:
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.
Storage: Store in closed vessels.

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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
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C8H10N2O
Molecular weight: 150.2

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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：

  2-乙酰氨基-6-甲基嘧啶 在 potassium permanganate 作用下， 以 水 为溶剂， 反应 0.58h， 以26%的产率得到6-乙酰氨基吡啶羧酸
  参考文献：
  名称：

  分子自组装的氢键控制：酰基氨基吡啶-羧酸衍生物在溶液和固态中的聚集行为

  摘要：

  在本文中，我们报告了一系列可以通过羧酸和氨基吡啶位点之间的双齿氢键相互作用聚集的酰基氨基吡啶-羧酸单体的设计，合成和研究。我们表明，在溶液中，聚集体的性质取决于单体的取代方式，并从NMR和质谱法中得出在某些情况下会发生环状缔合的证据。

  DOI：

  10.1016/s0040-4020(00)00733-x
• 作为产物：
  描述：

  5-酮基已腈 在 sodium hydroxide 、 硫酸羟胺 、 乙酰氯 作用下， 反应 6.0h， 生成 2-乙酰氨基-6-甲基嘧啶
  参考文献：
  名称：

  Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles

  摘要：

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).

  DOI：

  10.1021/jo00056a021

文献信息

• Highly Regioselective Palladium-Catalyzed C2-Amination of 2,4-Dichloropyridines: Scope and Limitations
  作者：Rémy Morgentin、Christian Delvare、Patrice Koza

  DOI：10.1055/s-0030-1260080

  日期：2011.8

  The use of palladium(0) enables a highly regioselective C-2 amination of 4,6-dichloronicotinonitrile. Coupling with aminoarenes that are N-acetyl-masked to limit cross-coupling overreaction, leads to 4-chloro-6-anilino nicotinonitrile compounds after deprotection in situ. The scope of these original conditions was evaluated.

  使用零价钯催化剂实现了对4,6-二氯烟腈的高度区域选择性的C-2胺化反应。通过与N-乙酰化保护的氨基芳烃进行偶联，以限制交叉偶联过度反应，然后在原位脱保护后得到4-氯-6-苯胺烟腈化合物。这些原始反应条件的适用范围得到了评估。
• B(C ₆ F ₅ ) ₃ ‐Catalyzed Deoxygenative Reduction of Amides to Amines with Ammonia Borane
  作者：Yixiao Pan、Zhenli Luo、Jiahong Han、Xin Xu、Changjun Chen、Haoqiang Zhao、Lijin Xu、Qinghua Fan、Jianliang Xiao

  DOI：10.1002/adsc.201801447

  日期：2019.5.14

  The first B(C6F5)3‐catalyzed deoxygenative reduction of amides into the corresponding amines with readily accessible and stable ammonia borane (AB) as a reducing agent under mild reaction conditions is reported. This metal‐free protocol provides facile access to a wide range of structurally diverse amine products in good to excellent yields, and various functional groups including those that are reduction‐sensitive

  据报道，在温和的反应条件下，用易于获得且稳定的氨硼烷（AB）作为还原剂，将酰胺进行的首次B（C 6 F 5）3催化脱氧还原为相应的胺。该无金属方案可轻松获得各种结构多样的胺产品，且收率高至优异，并且对各种官能团（包括对还原敏感的官能团）均具有良好的耐受性。该新方法也适用于手性酰胺底物，而不会破坏对映体的纯度。BF 3  OEt 2助催化剂在该反应中的作用是通过酰胺-硼加合物的原位形成来活化酰胺羰基。
• [EN] IMIDAZO[1,2-A]PYRAZINE MODULATORS OF THE ADENOSINE A2A RECEPTOR<br/>[FR] MODULATEURS DE 5,6-BICYCLO-IMIDAZO[1,2-A]PYRAZINE DU RÉCEPTEUR A2A DE L'ADÉNOSINE
  申请人：SELVITA S A

  公开号：WO2019002606A1

  公开（公告）日：2019-01-03

  The present invention relates to the compound of formula (I) and salts, stereoisomers, tautomers, isotopologues,or N-oxides thereof. The present invention is further concerned with the use of such a compound or salt, stereoisomer, tautomer, isotopologues,or N-oxide thereof as medicament and a pharmaceutical composition comprising said compound.

  本发明涉及式(I)的化合物及其盐、立体异构体、互变异构体、同位素同分异构体或N-氧化物。本发明进一步涉及将该化合物或盐、立体异构体、互变异构体、同位素同分异构体或N-氧化物用作药物的用途，以及包含该化合物的药物组合物。
• Deoxygenative Hydrogenation of Amides Catalyzed by a Well-Defined Iridium Pincer Complex
  作者：Ming-Lei Yuan、Jian-Hua Xie、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1021/acscatal.6b01019

  日期：2016.6.3

  The iridium-catalyzed highly chemoselective hydrogenation of amides to amines has been developed. Using a well-defined iridium catalyst bearing a P(O)C(O)P pincer ligand combined with B(C6F5)3, the C–O cleavage products are formed under mild reaction conditions. The reaction provides a new method for the preparation of amines from amides in good yield with high selectivity.

  已经开发了铱催化的酰胺高度化学选择性氢化成胺的方法。使用带有P（O）C（O）P钳形配体与B（C 6 F 5）3结合的明确定义的铱催化剂，在温和的反应条件下可形成C–O裂解产物。该反应提供了一种以高收率和高选择性从酰胺制备胺的新方法。
• Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines
  作者：Ming-Lei Yuan、Jian-Hua Xie、Qi-Lin Zhou

  DOI：10.1002/cctc.201600635

  日期：2016.10.6

  The hydrogenation of amides to amines has been developed by using the catalyst [Ru(H)2(CO)(Triphos)] (Triphos=1,1,1‐tri(diphenylphosphinomethyl)ethane) and catalytic boron Lewis acids such as B(C6F5)3 or BF3⋅Et2O as additives. The reaction provides an efficient method for the preparation of secondary amines from amides in good yields with high selectivity.

  已通过使用催化剂[Ru（H）2（CO）（Triphos）]（Triphos = 1,1,1,1-tri（diphenylphosphinomethyl）ethane）和催化硼路易斯酸（例如B（ ç 6 ˚F 5）3或BF 3 ⋅的Et 2 O作为添加剂。该反应提供了以高收率和高选择性从酰胺制备仲胺的有效方法。

表征谱图