3-氰基-6-羟基吡啶 | 94805-52-4

• 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-6-羟基吡啶
• 中文别名: 5-氰基-2(1H)-吡啶酮；2-羟基-5-氰基吡啶
• 英文名称: 6-hydroxynicotinonitrile
• 英文别名: 6-hydroxypyridine-3-carbonitrile；2-hydroxy-5-cyanopyridine；6-oxo-1H-pyridine-3-carbonitrile
• CAS: 94805-52-4
• 化学式: C₆H₄N₂O
• mdl: MFCD06656489
• 分子量: 120.111
• InChiKey: CCQUUHVUQQFTGV-UHFFFAOYSA-N

物化性质

• 熔点：
  256-258
• 沸点：
  332.7±35.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 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：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  请保持冷饮

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Cyano-2(1H)-pyridinone
Synonyms: 6-Hydroxynicotinonitrile; 5-Cyano-2-hydroxypyridine;

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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-Cyano-2(1H)-pyridinone
CAS number: 94805-52-4

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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: C6H4N2O
Molecular weight: 120.1

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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

制备方法与用途

用途

3-氰基-6-羟基吡啶是吡啶衍生物的一种，作为含能前体，它频繁被选作原料或母核用于医药和化工产品的制备。

制备

以6-氯吡啶-3-甲酰胺为起始物料，通过合成氰基并水解生成羟基的过程，最终得到目标化合物3-氰基-6-羟基吡啶。合成反应式如下图：

反应信息

• 作为反应物：
  描述：

  3-氰基-6-羟基吡啶 在 N,N-二甲基甲酰胺 氯化亚砜 作用下， 以95%的产率得到6-氯-3-氰基吡啶
  参考文献：
  名称：

  Practical Synthesis of (6-Chloro-3-pyridyl)methylamine by Highly Selective Hydrogenation of 6-Chloro-3-pyridinecarbonitrile with Improved Raney Nickel Catalyst

  摘要：

  本文描述了一种实用合成（6-氯-3-吡啶基）甲胺（1）的方法，该化合物是新烟碱类杀虫剂的重要中间体，采用对6-氯-3-吡啶腈（4）进行高度选择性的加氢反应。使用改进的Raney镍催化剂，该催化剂由低镍含量合金（镍38%，铝62%）制备，并在浸出铝后在水中进行热处理（98°C, 2小时），对4的选择性加氢反应非常有效。使用该催化剂对4进行加氢反应是在乙醇-水 [6:1 (v/v)] 和氨气的条件下，于50°C和1.2—1.4 kg cm-2的氢气压力下进行的，最终得到1的产率为86%，并生成脱氯副产物3-吡啶基甲胺，产率为2%。

  DOI：

  10.1246/bcsj.73.1227
• 作为产物：
  描述：

  3-氰基吡啶 以95%的产率得到3-氰基-6-羟基吡啶
  参考文献：
  名称：

  Practical Synthesis of (6-Chloro-3-pyridyl)methylamine by Highly Selective Hydrogenation of 6-Chloro-3-pyridinecarbonitrile with Improved Raney Nickel Catalyst

  摘要：

  本文描述了一种实用合成（6-氯-3-吡啶基）甲胺（1）的方法，该化合物是新烟碱类杀虫剂的重要中间体，采用对6-氯-3-吡啶腈（4）进行高度选择性的加氢反应。使用改进的Raney镍催化剂，该催化剂由低镍含量合金（镍38%，铝62%）制备，并在浸出铝后在水中进行热处理（98°C, 2小时），对4的选择性加氢反应非常有效。使用该催化剂对4进行加氢反应是在乙醇-水 [6:1 (v/v)] 和氨气的条件下，于50°C和1.2—1.4 kg cm-2的氢气压力下进行的，最终得到1的产率为86%，并生成脱氯副产物3-吡啶基甲胺，产率为2%。

  DOI：

  10.1246/bcsj.73.1227

文献信息

• [EN] PYRIDINONE- AND PYRIDAZINONE-BASED COMPOUNDS AND MEDICAL USES THEREOF<br/>[FR] COMPOSÉS À BASE DE PYRIDINONE ET DE PYRIDAZINONE ET UTILISATIONS MÉDICALES ASSOCIÉES
  申请人：HLA TIMOTHY

  公开号：WO2019173790A1

  公开（公告）日：2019-09-12

  The various examples presented herein are directed to compounds of the formula A-L1-Het1-L2-Cy1 or a pharmaceutical acceptable salt, polymorph, prodrug, solvate or clathrate thereof, wherein: A is cycloalkyl, aryl, arylalkyl or heterocyclyl; Het1 is heterocyclyl containing at least two heteroatoms; Cy1 is a heterocyclyl; L1 is a bond, alkyl, alkenyl or alkynyl linker; L2 is an acyl or alkyl linker; and A and Cy1 are different. The compounds are useful in the treatment of fibrotic diseases, abnormal vascular leak and pathological angiogenesis.

  本文提供的各种示例涉及到以下公式的化合物A-L1-Het1-L2-Cy1或其药用可接受的盐、多型体、前药、溶剂合物或包合物，其中：A为环烷基、芳基、芳基烷基或杂环烷基；Het1为含有至少两个杂原子的杂环烷基；Cy1为杂环烷基；L1为键、烷基、烯基或炔基连接物；L2为酰基或烷基连接物；A和Cy1不同。这些化合物在治疗纤维化疾病、异常血管渗漏和病理性血管生成方面具有用途。
• [EN] TRICYCLIC PYRAZOLE KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASES A BASE DE TYRAZOLES TRICYCLIQUES
  申请人：ABBOTT LAB

  公开号：WO2005095387A1

  公开（公告）日：2005-10-13

  Compounds of the present invention are useful for inhibiting protein tyrosine kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.

  本发明的化合物对抑制蛋白酪氨酸激酶具有用处。还公开了制备这些化合物的方法、含有这些化合物的组合物以及使用这些化合物进行治疗的方法。
• Inhibitors of c-Jun N-terminal kinases
  申请人：Liu Gang

  公开号：US20060173050A1

  公开（公告）日：2006-08-03

  The present invention relates to compounds that are inhibitors of c-jun N-terminal kinase 1, 2, or 3 (JNK1, JNK2, or JNK3), compositions containing the compounds and the use of the compounds in the prevention or treatment of disorders regulated by the activation of JNK1, JNK2 and JNK3.

  本发明涉及作为c-jun N-末端激酶1、2或3（JNK1、JNK2或JNK3）抑制剂的化合物，包含这些化合物的组合物以及这些化合物在预防或治疗由JNK1、JNK2和JNK3激活调控的疾病中的用途。
• PYRROLIDINE ETHER DERIVATIVES AS NK3 RECEPTOR ANTAGONISTS
  申请人：Jablonski Philippe

  公开号：US20090306043A1

  公开（公告）日：2009-12-10

  The present invention relates to compounds of formula I wherein R 1 , R 2 , R 3 , R′, Ar, m, n, and o are as defined herein. The invention also relates to pharmaceutical compositions containing compounds of formula I and methods for the manufacture of such compounds and compositions. Compounds of the invention are high potential NK-3 receptor antagonists for the treatment of depression, pain, psychosis, Parkinson's disease, schizophrenia, anxiety and attention deficit hyperactivity disorder (ADHD).

  本发明涉及式I的化合物，其中R1、R2、R3、R′、Ar、m、n和o如本文所定义。该发明还涉及含有式I化合物的药物组合物，以及制备这种化合物和组合物的方法。本发明的化合物是用于治疗抑郁症、疼痛、精神病、帕金森病、精神分裂症、焦虑和注意力缺陷多动障碍（ADHD）的高潜力NK-3受体拮抗剂。
• [EN] (AZA)INDAZOLYL-ARYL SULFONAMIDE AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS<br/>[FR] (AZA) INDAZOLYL-ARYLE SULFONAMIDE ET COMPOSÉS APPARENTÉS ET LEUR UTILISATION DANS LE TRAITEMENT D'ÉTATS MÉDICAUX
  申请人：HIBERCELL INC

  公开号：WO2020210828A1

  公开（公告）日：2020-10-15

  The invention provides (aza)indazolyl-aryl sulfonamide and related compounds, pharmaceutical compositions, and their use in the treatment of medical conditions, such as cancer, and in inhibiting GCN2 activity.

  这项发明提供了(aza)吲哚基芳基磺酰胺及相关化合物、药物组合物，以及它们在治疗医疗状况（如癌症）和抑制GCN2活性中的用途。