3-氰基-4-羟基-2(1H)-吡啶酮 | 5657-64-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 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: 3-氰基-4-羟基-2(1H)-吡啶酮
• 英文名称: 2,4-dihydroxy-nicotinonitrile
• 英文别名: 2,4-Dihydroxy-nicotinonitril；4-Hydroxy-2-oxo-1,2-dihydropyridine-3-carbonitrile；4-hydroxy-2-oxo-1H-pyridine-3-carbonitrile
• CAS: 5657-64-7
• 化学式: C₆H₄N₂O₂
• mdl: MFCD09258786
• 分子量: 136.11
• InChiKey: FQLSOJBBTVEIHX-UHFFFAOYSA-N

物化性质

• 沸点：
  301.2±42.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 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：
  73.1
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Cyano-4-hydroxy-2(1H)-pyridinone
Synonyms: 4-Hydroxy-2-oxo-1,2-dihydropyridine-3-carbonitrile

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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: 3-Cyano-4-hydroxy-2(1H)-pyridinone
CAS number: 5657-64-7

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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: C6H4N2O2
Molecular weight: 136.1

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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.

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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-氰基-4-羟基-2(1H)-吡啶酮 在 硫酸 作用下， 生成 1,2-二氢-4-羟基-2-氧代-3-吡啶羧酸
  参考文献：
  名称：

  Schroeter et al., Chemische Berichte, 1932, vol. 65, p. 432,441

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯-1,2-二氢-4-羟基-2-氧代-3-吡啶甲腈 在 硫酸 、 锌 作用下， 生成 3-氰基-4-羟基-2(1H)-吡啶酮
  参考文献：
  名称：

  Schroeter et al., Chemische Berichte, 1932, vol. 65, p. 432,441

  摘要：

  DOI：

文献信息

• PHOSPHADIAZINE HCV POLYMERASE INHIBITORS I AND II
  申请人：Dousson Cyril

  公开号：US20090060866A1

  公开（公告）日：2009-03-05

  Provided herein are phosphadiazine polymerase inhibitor, for example, of any of Formula I, II, III, I′, II′, I″, II″, Ia, IIa, or IIIa, pharmaceutical compositions comprising the compounds, and processes of preparation thereof. Also provided are methods of their use for the treatment of an HCV infection in a host in need thereof.

  本发明提供了磷二嗪聚合酶抑制剂，例如任何式I、II、III、I′、II′、I″、II″、Ia、IIa或IIIa的化合物，包含这些化合物的药物组合物，以及它们的制备方法。还提供了用于治疗宿主中HCV感染的方法。
• Synthesis and DABCO‐induced demethylation of 3‐cyano‐4‐methoxy‐2‐pyridone derivatives
  作者：Jing Li、Hong‐Ru Tan、Yu‐Long An、Zhi‐Yu Shao、Sheng‐Yin Zhao

  DOI：10.1002/jhet.3783

  日期：2020.1

  An efficient method for synthesis and demethylation of 3‐cyano‐4‐methoxy‐2‐pyridone derivatives has been developed. DABCO‐induced demethylation can lead to 3‐cyano‐4‐hydroxy‐2‐pyridones in DMF at 90°C with high yield. The protocol is applicable for the synthesis of 3‐cyano‐4‐hydroxy‐2‐pyridone derivatives. The method is simple, efficient, and practical.

  已开发出一种有效的3-氰基-4-甲氧基-2-吡啶酮衍生物合成和去甲基化的方法。在90°C下，DABCO诱导的去甲基化可以导致DMF中的3-氰基-4-羟基-2-吡啶酮的高收率。该协议适用于3-氰基-4-羟基-2-吡啶酮衍生物的合成。该方法简单，高效，实用。
• [DE] VERFAHREN ZUR HERSTELLUNG VON 2,6-DICHLOR-5-FLUORNICOTINONITRIL UND DIE CHEMISCHE VERBINDUNG 3-CYANO-2-HYDROXY-5-FLUORPYRID-6-ON-MONONATRIUMSALZ SOWIE DESSEN TAUTOMERE<br/>[EN] METHOD FOR THE PRODUCTION OF 2,6-DICHLORO-5-FLUORONICOTINONITRILE AND THE CHEMICAL COMPOUND 3-CYANO-2-HYDROXY-5-FLUOROPYRIDE-6-ONE-MONOSODIUM SALT AND ITS TAUTOMERS<br/>[FR] PROCEDE DE PREPARATION DE 2,6-DICHLORO-5-FLUORONICOTINONITRILE ET COMPOSE CHIMIQUE 3-CYANO-2-HYDROXY-5-FLUOROPYRIDE-6-ONE-SEL MONOSODIQUE AINSI QUE SES TAUTOMERES
  申请人：BAYER AKTIENGESELLSCHAFT

  公开号：WO1998043958A1

  公开（公告）日：1998-10-08

  (DE) 2,6-Dichlor-5-fluornicotinonitril ist in einer vorteilhaften Weise zugänglich durch Umsetzung von 3-Cyano-2-hydroxy-5-fluorpyrid-6-on und/oder seine Tautomeren und/oder seine Salze und/oder deren Tautomere mit Phosphortrichlorid und Chlorgas in einem Lösungsmittel unter Zusatz eines basischen Katalysators bei Temperaturen von 30-300 °C und anschließender Hydrolyse. Das einsetzbare 3-Cyano-2-hydroxy-5-fluorpyrid-6-on-mononatriumsalz ist eine neue chemische Verbindung, die auf einfache Weise aus 3-Cyano-2-hydroxy-5-fluorpyrid-6-on und/oder dessen Tautomeren durch Umsetzung mit einem Alkoholat und Ausfällung mit einer mittelstarken Säure zugänglich ist.(EN) The invention relates to 2,6-dichloro-5-fluoronicotinitrile which can be advantageously obtained by reacting 3-cyano-2-hydroxy-5-fluoropyride-6-one and/or its tautomers and/or its salts and/or their tautomers with phosphorus trichloride and chloric gas in a solvent with addition of a basic catalyst at temperatures between 30 and 300 °C, and then by hydrolysis. The 3-cyano-2-hydroxy-5-fluoropyride-6-one-monosodium salt which can be used is a new chemical compound that is easy to obtain from 3-cyano-2-hydroxy-5-fluoropyride-6-one and/or its tautomers by reaction with alcoholate and precipitation with a moderately weak acid.(FR) L'invention concerne du 2,6-dichloro-5-fluoroniconitrile pouvant être avantageusement obtenu par réaction de 3-cyano-2-hydroxy-5-fluoropyride-6-one et/ou ses tautomères et/ou ses sels et/ou leurs tautomères avec du trichlorure de phosphore et du chlore gazeux dans un solvant, sous adjonction d'un catalyseur basique à des températures comprises entre 30 et 300 °C, puis par hydrolyse. Le 3-cyano-2-hydroxy-5-fluoropyride-6-one-sel monosodique à utiliser est un nouveau composé chimique facile à obtenir à partir de 3-cyano-2-hydroxy-5-fluoropyride-6-one et/ou ses tautomères, par réaction avec de l'alcoolat et par précipitation avec de l'acide modérément faible.

  (德) 2,6-二氯-5-氟烟腈可以通过将3-氰基-2-羟基-5-氟吡啶-6-酮及其/或其异构体和/或其盐及其/或其异构体与三氯化磷和氯气在溶剂中加入碱性催化剂，在30-300°C的温度下反应，然后进行水解，以一种有利的方式获得。可用的3-氰基-2-羟基-5-氟吡啶-6-酮单钠盐是一种新的化学化合物，可以通过将3-氰基-2-羟基-5-氟吡啶-6-酮及其/或其异构体与醇盐反应并用中等弱酸沉淀，以简单的方式获得。 (英) 本发明涉及2,6-二氯-5-氟烟腈，可以通过将3-氰基-2-羟基-5-氟吡啶-6-酮及其/或其异构体和/或其盐及其/或其异构体与三氯化磷和氯气在溶剂中加入碱性催化剂，在30-300°C的温度下反应，然后进行水解以有利的方式获得。可用的3-氰基-2-羟基-5-氟吡啶-6-酮单钠盐是一种新的化学化合物，可以通过将3-氰基-2-羟基-5-氟吡啶-6-酮及其/或其异构体与醇盐反应并用中等弱酸沉淀，以简单的方式获得。 (法) 本发明涉及2,6-二氯-5-氟烟腈，可以通过将3-氰基-2-羟基-5-氟吡啶-6-酮及其/或其异构体和/或其盐及其/或其异构体与三氯化磷和氯气在溶剂中加入碱性催化剂，在30-300°C的温度下反应，然后进行水解以有利的方式获得。可用的3-氰基-2-羟基-5-氟吡啶-6-酮单钠盐是一种新的化学化合物，可以通过将3-氰基-2-羟基-5-氟吡啶-6-酮及其/或其异构体与醇盐反应并用中等弱酸沉淀，以简单的方式获得。 总结：该专利描述了一种制备2,6-二氯-5-氟烟腈的方法，通过特定的化学反应和水解步骤，并提到了一种新的化学化合物——3-氰基-2-羟基-5-氟吡啶-6-酮单钠盐的制备方法。这些信息对于理解相关的化学合成过程和化合物性质具有重要意义。
• VERFAHREN ZUR HERSTELLUNG VON 2,6-DICHLOR-5-FLUORNICOTINONITRIL UND DIE CHEMISCHE VERBINDUNG 3-CYANO-2-HYDROXY-5-FLUORPYRID-6-ON-MONONATRIUMSALZ SOWIE DESSEN TAUTOMERE
  申请人：BAYER AG

  公开号：EP0973745A1

  公开（公告）日：2000-01-26
• SUBSTITUTED PYRIDONE DERIVATIVES AS PDE10 INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2922543B1

  公开（公告）日：2017-05-24