2-氨基-4-氟吡啶 | 944401-77-8

• 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 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氨基-4-氟吡啶
• 英文名称: 4-fluoropyridin-2-amine
• 英文别名: 2-amino-4-fluoropyridine；4-fluoro-2-aminopyridine
• CAS: 944401-77-8
• 化学式: C₅H₅FN₂
• mdl: MFCD09260906
• 分子量: 112.107
• InChiKey: WCCFLOQQACDOAX-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  211.5±20.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  冷藏保存。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-4-fluoropyridine
Synonyms: 4-Fluoropyridin-2-amine

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H319: Causes serious eye 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-Amino-4-fluoropyridine
CAS number: 944401-77-8

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels, refrigerated.

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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: C5H5FN2
Molecular weight: 112.1

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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, hydrogen fluoride.

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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

2-氨基-4-氟吡啶是一种重要的有机合成和医药中间体。

反应信息

• 作为反应物：
  描述：

  2-氨基-4-氟吡啶 在 lithium hydroxide monohydrate 、 potassium tert-butylate 、 水 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 乙醇 、 二氯甲烷 、 叔丁醇 、 苯 为溶剂， 反应 38.33h， 生成 N-(3-ethyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)-7-((3S,4S)-4-hydroxypyrrolidin-3-yloxy)imidazo[1,2-a]pyridine-3-carboxamide
  参考文献：
  名称：

  [EN] SUBSTITUTED N-(1H-INDAZOL-4-YL)IMIDAZO[1, 2-A]PYRIDINE-3- CARBOXAMIDE COMPOUNDS AS CFMS INHIBITORS
  [FR] COMPOSÉS À BASE DE N-(1H-INDAZOL-4-YL)IMIDAZO[1,2-A]PYRIDINE-3-CARBOXAMIDE SUBSTITUÉ UTILES EN TANT QU'INHIBITEURS DE CFMS

  摘要：

  式(I)的化合物及其药学上可接受的盐，其中R1、R2、R3、R4和R5的含义如规范中所述，是cFMS的抑制剂，并且在治疗与骨相关的疾病、癌症、自身免疫性疾病、炎症性疾病、心血管疾病和疼痛方面是有用的。

  公开号：

  WO2011079076A1
• 作为产物：
  描述：

  2-氨基-4-氯吡啶 在 sodium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到2-氨基-4-氟吡啶
  参考文献：
  名称：

  一种2-氨基-4-氟吡啶的制备方法

  摘要：

  本发明公开了一种2‑氨基‑4‑氟吡啶的制备方法，合成步骤为：步骤1，以2‑吡啶羧酸为原料，在氯化亚砜及盐的存在下，反应得到4‑氯吡啶‑2‑酰氯,4‑氯吡啶‑2‑酰氯在氨的存在下，得到4‑氯吡啶‑2‑酰胺；步骤2，4‑氯吡啶‑2‑酰胺经过霍夫曼酰胺降级反应得到2‑氨基‑4‑氯吡啶；步骤3，2‑氨基‑4‑氯吡啶经过卤素交换得到2‑氨基‑4‑氟吡啶。本发明解决了现有制备方法合成路线长、操作繁琐、三废污染量大、原子经济差、收率低、制造成本高等问题。

  公开号：

  CN108440402A
• 作为试剂：
  描述：

  (3R,5S,6R)-6-sec-butyl-tetrahydro-3,5-dimethylpyran-2-one 、 1,4-Dihydroxy-5-phenylpyridin-2-one 在 二异丁基氢化铝 、 2-氨基-4-氟吡啶 作用下， 以 正己烷 、 二氯甲烷 、 1,4-二氧六环 为溶剂， 反应 20.5h， 以77.778%的产率得到
  参考文献：
  名称：

  Concise Synthesis of Reduced Propionates by Stereoselective Reductions Combined with the Kobayashi Reaction

  摘要：

  A concise and straightforward synthesis of 2,4,6-trimethyloctanoates was established by using the sequence of the vinylogous Mukalyama aldol reaction and regio- and stereoselective reduction reactions. All Isomers were obtained selectively in a few steps. The short step synthesis of septoriamycin A, an antimalarial and antileishmanial agent, has been achieved by this methodology.

  DOI：

  10.1021/ol401406m

文献信息

• [EN] SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS<br/>[FR] ANALOGUES D'URÉE PONTÉS SUBSTITUÉS EN TANT QUE MODULATEURS DE SIRTUINE
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2016079709A1

  公开（公告）日：2016-05-26

  The present invention relates to novel substituted bridged urea analog compounds of Formula (I) or pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions, processes for making and use of such compounds, alone or in combination with other therapeutic agents, as Sirtuin Modulators useful for increasing lifespan of a cell, and for use in treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity.

  本发明涉及一种新型的取代桥式脲类似物化合物，其化学式为（I）或其药学上可接受的盐，相应的药物组合物，制备这种化合物的方法以及单独使用或与其他治疗剂联合使用的这些化合物作为Sirtuin调节剂，可用于增加细胞寿命，并用于治疗和/或预防各种疾病和紊乱，包括但不限于与衰老或压力、糖尿病、肥胖、神经退行性疾病、心血管疾病、血液凝块紊乱、炎症、癌症和/或潮红有关的疾病或紊乱，以及那些会受益于增加线粒体活性的疾病或紊乱。
• [EN] QUINOLINE AND QUINAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS QUINOLÉINE ET QUINAZOLINE
  申请人：ACERTA PHARMA BV

  公开号：WO2016055982A1

  公开（公告）日：2016-04-14

  In some embodiments, the invention relates to quinazoline and quinoline compounds of Formula I: (I) or a pharmaceutically acceptable salt thereof, or to pharmaceutical compositions comprising these compounds and to their use in therapy. In particular, in some embodiments, the present invention relates to quinazoline and quinoline compounds, pharmaceutical compositions thereof, and the use of the compounds and pharmaceutical compositions in the treatment of Bruton's tyrosine kinase (BTK) mediated disorders.

  在某些实施例中，该发明涉及式I的喹唑啉和喹啉化合物：(I)或其药用可接受盐，或者涉及包含这些化合物的药物组合物以及它们在治疗中的应用。具体而言，在某些实施例中，本发明涉及喹唑啉和喹啉化合物、其药物组合物以及这些化合物和药物组合物在治疗布鲁顿氨基酸激酶（BTK）介导的疾病中的应用。
• Four-component synthesis of 3-aminomethylated imidazoheterocycles in EtOH under catalyst-free, oxidant-free and mild conditions
  作者：Qing-Wen Gui、Bin-Bin Wang、Sha Zhu、Fu-Long Li、Meng-Xue Zhu、Min Yi、Jia-Ling Yu、Zhi-Lin Wu、Wei-Min He

  DOI：10.1039/d1gc01017d

  日期：——

  With green ethanol as the sole solvent, various 3-aminomethylated imidazoheterocycles were efficiently synthesized in one step through a four-component reaction of equimolar cheap and commercially available reactants at ambient temperature under metal-free, oxidant-free and mild conditions.

  以绿色乙醇为唯一溶剂，在环境温度，无金属，无氧化剂和温和的条件下，通过等摩尔廉价且可商购的反应物的四组分反应，一步有效地合成了各种3-氨基甲基化的咪唑杂环。
• Copper-catalysed amination of alkyl iodides enabled by halogen-atom transfer
  作者：Bartosz Górski、Anne-Laure Barthelemy、James J. Douglas、Fabio Juliá、Daniele Leonori

  DOI：10.1038/s41929-021-00652-8

  日期：——

  the fact that nucleophilic displacement (SN2) of alkyl halides with nitrogen nucleophiles is one of the first reactions introduced in organic chemistry teaching, its practical utilization is largely limited to unhindered (primary) or activated (α-carbonyl, benzylic) substrates. Here, we demonstrate an alternative amination strategy where alkyl iodides are used as radical precursors instead of electrophiles

  尽管卤代烷与氮亲核试剂的亲核置换 (S N 2) 是有机化学教学中最早引入的反应之一，但其实际应用在很大程度上仅限于不受阻碍的（初级）或活化的（α-羰基、苄基）底物. 在这里，我们展示了一种替代胺化策略，其中烷基碘被用作自由基前体而不是亲电子试剂。使用 α-氨基烷基自由基可以通过卤素原子转移将碘化物有效地转化为相应的烷基自由基，而铜催化在室温下组装sp 3 C-N 键。该过程提供 S N2 样的可编程性以及在几种密集功能化药物的后期功能化中的应用证明了其在制备有价值的N-烷基化药物类似物方面的实用性。
• Electrochemical Oxidative C—H Sulfenylation of Imidazopyridines with Hydrogen Evolution
  作者：Yong Yuan、Yangmin Cao、Jin Qiao、Yueping Lin、Xiaomei Jiang、Yaqing Weng、Shan Tang、Aiwen Lei

  DOI：10.1002/cjoc.201800405

  日期：2019.1

  Selective oxidative C—H sulfenylation of imidazopyridine heterocycles is achieved using an undivided electrolytic cell. The reaction avoids the use of stoichiometric amount of external chemical oxidant and produces hydrogen gas as the only byproduct. Both aryl and aliphatic thiols demonstrate good reactivity for C—S bond formation.

  咪唑并吡啶杂环的选择性氧化CH H亚磺酰基化反应是通过使用未分割的电解池实现的。该反应避免使用化学计量的外部化学氧化剂，并产生氢气作为唯一的副产物。芳基和脂族硫醇均显示出对Cs键形成的良好反应性。