3-(4-氟苯基)-5-吡啶羧酸 | 364064-17-5

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 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: 3-(4-氟苯基)-5-吡啶羧酸
• 中文别名: 5-(4-氟苯基)烟酸
• 英文名称: EMD 50929
• 英文别名: 5-(4-fluorophenyl)pyridine-3-carboxylic acid；3-(4-fluorophenyl)-pyridine-5-carbonic acid；5-(4-fluorophenyl)nicotinic acid
• CAS: 364064-17-5
• 化学式: C₁₂H₈FNO₂
• 分子量: 217.199
• InChiKey: KISDAKHYANOMTN-UHFFFAOYSA-N

物化性质

• 沸点：
  415.7±35.0 °C(Predicted)
• 密度：
  0.5 g/cm3 (20℃)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  4

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-(4-Fluorophenyl)nicotinic acid
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: 5-(4-Fluorophenyl)nicotinic acid
CAS number: 364064-17-5

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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: C12H8FNO2
Molecular weight: 217.2

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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, 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

反应信息

• 作为反应物：
  描述：

  3-(4-氟苯基)-5-吡啶羧酸 在 palladium diacetate 、 三苯基膦 二碳酸二叔丁酯 、 氢气 作用下， 以 四氢呋喃 为溶剂， 100.0 ℃ 、11.0 MPa 条件下， 反应 24.0h， 生成 5-(4-氟苯基)-3-吡啶甲醛
  参考文献：
  名称：

  [DE] VERFAHREN ZUR HERSTELLUNG VON 5-ARYLNICOTINALDEHYDEN
  [EN] METHOD FOR THE PRODUCTION OF 5-ARYL NICOTINALDEHYDES
  [FR] PROCEDE POUR LA PRODUCTION DE 5-ARYLNICOTINALDEHYDES

  摘要：

  本发明涉及一种通过在Di-tert.-butyldicarbonat存在下，利用磷配体稳定的钯络合物进行催化加氢，从而通过还原相应的5-芳基烟酸制备5-芳基烟醛的方法。其特征在于，钯络合物与5-芳基烟酸的摩尔比在1:500至1:8000之间，而5-芳基烟酸与Di-tert.-butyldicarbonat的摩尔比在1:1至1:5之间。

  公开号：

  WO2005123682A1
• 作为产物：
  描述：

  ethyl 5-(4-fluorophenyl)nicotinate 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 3-(4-氟苯基)-5-吡啶羧酸
  参考文献：
  名称：

  Subtype-selective Nav1.8 sodium channel blockers: Identification of potent, orally active nicotinamide derivatives

  摘要：

  A series of aryl-substituted nicotinamide derivatives with selective inhibitory activity against the Na(v)1.8 sodium channel is reported. Replacement of the furan nucleus and homologation of the anilide linker in subtype-selective blocker A-803467 (1) provided potent, selective derivatives with improved aqueous solubility and oral bioavailability. Representative compounds from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.121

文献信息

• Suzuki coupling reaction for the solid-phase preparation of 5-substituted nicotinic acid derivatives
  作者：Joan-Carles Fernàndez、Laia Solé-Feu、Dolors Fernández-Forner、Natalia de la Figuera、Pilar Forns、Fernando Albericio

  DOI：10.1016/j.tetlet.2004.11.153

  日期：2005.1

  The application of the Suzuki coupling reaction to the preparation of small combinatorial libraries using 5-bromonicotinic acid as a scaffold onto three different types of solid support (Wang, Rink, and BAL resin) is described.

  描述了将Suzuki偶联反应用于使用5-溴烟酸作为支架在三种不同类型的固体支持物（Wang，Rink和BAL树脂）上制备小的组合文库的应用。
• Method for producing 5-aryl nicotinaldehydes
  申请人：——

  公开号：US20030055259A1

  公开（公告）日：2003-03-20

  The invention relates to a process for the preparation of 5-arylnicotinaldehydes by reduction of the corresponding 5-arylnicotinic acids by catalytic hydrogenation in the presence of carboxylic anhydrides in which the catalyst used is a palladium/ligand complex, characterized in that the molar ratio between palladium and ligand is from 1:5 to 1:15 in the case of monodentate ligands and from 1:2.5 to 1:7.5 in the case of bidentate ligands.

  该发明涉及一种通过在羧酸酐存在下催化氢化还原相应的5-芳基烟酸制备5-芳基烟醛的方法，所使用的催化剂为钯/配体复合物，其特征在于单齿配体情况下钯和配体之间的摩尔比为1:5至1:15，双齿配体情况下为1:2.5至1:7.5。
• [DE] VERFAHREN ZUR HERSTELLUNG VON NICOTINALDEHYDEN<br/>[EN] METHOD FOR THE PRODUCTION OF NICOTINALDEHYDES<br/>[FR] PROCEDE POUR PRODUIRE DES ALDEHYDES DE NICOTINE
  申请人：MERCK PATENT GMBH

  公开号：WO2004094383A1

  公开（公告）日：2004-11-04

  Die Erfindung betrifft ein Verfahren zur Herstellung von Nicotinaldehyden durch Reduktion der entsprechenden Nicotinsäure-Morpholinamide.

  这项发明涉及一种通过还原相应的尼古丁酸吗啡酰胺制备尼古丁醛的方法。
• Catalytic Syntheses of N-Heterocyclic Ynones and Ynediones by In Situ Activation of Carboxylic Acids with Oxalyl Chloride
  作者：Christina Boersch、Eugen Merkul、Thomas J. J. Müller

  DOI：10.1002/anie.201103296

  日期：2011.10.24

  bottleneck: α‐Keto carboxylic acids and N‐heterocyclic carboxylic acids are activated in situ with oxalyl chloride then catalytically alkynylated to give ynediones and N‐heterocyclic ynones efficiently in a one‐pot fashion. 5‐Acylpyrazoles and 2‐phenylaminopyrimidines, potentially interesting for pharmaceutical applications, are readily synthesized in concise one‐pot, three‐component syntheses.

  突破瓶颈：使用草酰氯将α-酮基羧酸和N-杂环羧酸原位活化，然后进行催化炔基化反应，以单锅方式有效地产生乙炔和N-杂环炔酮。5-酰基吡唑和2-苯基氨基嘧啶可能在药物应用中很有趣，它们可以通过简单的一锅，三成分合成方法轻松合成。
• Biotransformation of fluorophenyl pyridine carboxylic acids by the model fungus <i>Cunninghamella elegans</i>
  作者：William Palmer-Brown、Brian Dunne、Yannick Ortin、Mark A. Fox、Graham Sandford、Cormac D. Murphy

  DOI：10.1080/00498254.2016.1227109

  日期：2017.9.2

  fluorinated phenyl pyridine carboxylic acids were incubated with the fungus Cunninghamella elegans, which is an established model of mammalian drug metabolism. 3. 19F NMR spectroscopy established the degree of biotransformation, which varied depending on the position of fluorine substitution, and gas chromatography–mass spectrometry (GC–MS) identified alcohols and hydroxylated carboxylic acids as metabolites

  1.氟在新药的设计中起着关键作用，最近FDA批准了两种氟化药物，泰地唑磷酸酯和vorapaxar，它们都含有氟苯基吡啶基部分。 2.为了研究该组可能的I期（氧化）代谢命运，将各种氟化苯基吡啶羧酸与线虫Cunninghamella elegans一起孵育，该真菌是哺乳动物药物代谢的既定模型。 3.  19 F NMR光谱确定了生物转化的程度，其变化取决于氟取代的位置，气相色谱-质谱（GC-MS）将醇和羟基化的羧酸鉴定为代谢物。通过核磁共振波谱（NMR）在结构上进一步表征了羟基化的代谢产物，这表明羟基化发生在4'位置。那个位置的氟阻止了羟基化。 4.氟苯基吡啶羧酸不能被大鼠肝微粒体生物转化，这是抑制作用的结果，因此，真菌模型对于获得代谢产物以建立分解代谢机制至关重要。