2-羟基异烟酸 | 22282-72-0

• 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-羟基异烟酸
• 中文别名: 2-羟基吡啶-4-甲酸；2-羟基-4-吡啶羧酸2-HYDROXY-4-PYRIDINECARBOXYLICACID；2-羟基-4-嘧啶羧基酸；2-羟基-4-吡啶甲酸
• 英文名称: 2-hydroxyisonicotinic acid
• 英文别名: 2-hydroxypyridine-4-carboxylic acid；2-oxo-1H-pyridine-4-carboxylic acid
• CAS: 22282-72-0
• 化学式: C₆H₅NO₃
• mdl: MFCD00955759
• 分子量: 139.111
• InChiKey: BXHCJLRTXPHUGH-UHFFFAOYSA-N

物化性质

• 熔点：
  300
• 沸点：
  384.0±42.0 °C(Predicted)
• 密度：
  1.451±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 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
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Hydroxyisonicotinic acid
Product Name:
Synonyms: 2-Hydroxy-4-pyridinecarboxylic acid; 4-Carboxy-2(1H)-pyridinone

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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
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
2-Hydroxyisonicotinic acid
Ingredient name:
CAS number: 22282-72-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H5NO3
Molecular weight: 139.1

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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

2-羟基异烟酸在常温常压下为白色固体粉末状。其分子中的羟基和双键会互变异构形成酰胺结构，主要用作有机合成和医药化学中间体，可用于合成吡啶衍生的含氮配体。

合成方法

向2-氯异烟酸（5.00克，31.7毫摩尔）中慢慢地加入90毫升浓盐酸。将悬浮液加热至140-150℃（油浴），得到的反应物在加热后会观察到逐渐变成澄清溶液，但在加热24小时后又变成了悬浮液。再往反应体系中加入20毫升盐酸，反应物变得清澈，继续加热24小时。之后再加入20毫升盐酸，并将反应物在反应热下搅拌12小时。反应物在冰浴中冷却过程中可以观察到有固体从溶液中析出。

将反应混合物用等体积的冰水稀释并过滤，滤饼用冷水清洗，沉淀物在高真空下干燥即可得到纯的2-羟基异烟酸，为白色固体，产量3.92克，收率89%。

图 2-羟基异烟酸的合成路线

反应信息

• 作为反应物：
  描述：

  2-羟基异烟酸 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到2-氧代哌啶-4-羧酸
  参考文献：
  名称：

  从2-吡嗪酮，2-羟基嘧啶或2-吡啶酮分别高效制备α-，β-，γ-或δ-氨基酸的两步法

  摘要：

  据报道，从2-吡啶酮，2-吡嗪酮或2-羟基嘧啶及其衍生物制备各种α-，β-，γ-和δ-氨基酸的方法是实用，有效的两步程序。该程序适合扩大规模，在大多数情况下，无需色谱纯化产品。这种方法很有用，特别是在合成其他方法无法获得的氨基酸或氘代氨基酸时。

  DOI：

  10.1002/ejoc.201801134
• 作为产物：
  描述：

  异烟酸 在 水 、 氧气 作用下， 生成 2-羟基异烟酸
  参考文献：
  名称：

  水中的三种羧基吡啶的光化学：pH依赖性反应。

  摘要：

  通过激光闪光光解法和产物研究研究了邻，间和对羧基吡啶（pK（a）（1）= 1.0-2.1和pK（a）（2）= 4.7-5.3）的光化学。在pH 4的条件下，通过激光闪光光解法检测到分配给三重态的脉冲结束瞬态。此外，在pH 4时会发生脱羧反应。在pH> 4时，由于容易进行脱羧过程。提出了考虑pH值和羧基吡啶浓度均依赖于小φ的反应方案。这项研究指出了取决于起始化合物的电离状态和异构体取代的羧基吡啶反应性的独特模式。自由基阴离子会以羧基吡啶基自由基的形式逸出，而自由基阳离子则可能在pH 4时会发生脱羧反应。在pH> 4时，由于容易进行脱羧过程。提出了考虑pH值和羧基吡啶浓度均依赖于小φ的反应方案。这项研究指出了取决于起始化合物的电离状态和异构体取代的羧基吡啶反应性的独特模式。自由基阴离子会以羧基吡啶基自由基的形式逸出，而自由基阳离子则可能在pH 4时会发生脱羧反应。 pH> 4时，由于容易进行脱

  DOI：

  10.1039/b401551g
• 作为试剂：
  描述：

  2-甲基-2-丁烯 、 2-苯基-1-丙烯 在 iron(III) chloride 、 bismuth(III) nitrate 、 2-羟基异烟酸 作用下， 以 乙醇 、 丙酮 、 甲苯 为溶剂， 以89.5 %的产率得到1,1,2,3,3-五甲基-2H-茚
  参考文献：
  名称：

  一种金属络合物催化剂及其在制备1,1,2,3,3-五甲基茚满中的应用

  摘要：

  本发明公开了一种金属络合物催化剂及其在制备1,1,2,3,3‑五甲基茚满中的应用，金属络合物催化剂的制备方法包括以下步骤：（1）将有机配体分散于有机溶剂中，得到溶液A；（2）将含活性金属的金属化合物溶解得到溶液B；（3）在50~70℃条件下，将溶液A和溶液B混合，搅拌2~4小时，充分混合，得到所述金属络合物催化剂。将该催化剂用于1,1,2,3,3‑五甲基茚满的制备时，反应条件温和，转化率和选择性高，并且对环境友好。

  公开号：

  CN115850349A

文献信息

• [EN] DOPAMINE D3 RECEPTOR ANTAGONISTS HAVING A BICYCLO MOIETY<br/>[FR] ANTAGONISTES DU RÉCEPTEUR D3 DE LA DOPAMINE AYANT UN FRAGMENT BICYCLO
  申请人：INDIVIOR UK LTD

  公开号：WO2017021920A1

  公开（公告）日：2017-02-09

  The disclosure provides compounds having formula (I), wherein the substituents are as defined herein. The compounds are useful for modulating the dopamine D3 receptor and for treating conditions associated therewith, such as addictions, drug dependency, and psychiatric conditions.

  该披露提供了具有化学式（I）的化合物，其中取代基如本文所定义。这些化合物可用于调节多巴胺D3受体，并用于治疗与之相关的疾病，如成瘾、药物依赖和精神疾病。
• 1,2,4-Triazolyl octahydropyrrolo[2,3-b]pyrroles: A new series of potent and selective dopamine D3 receptor antagonists
  作者：Fabrizio Micheli、Andrea Bernardelli、Federica Bianchi、Simone Braggio、Laura Castelletti、Palmina Cavallini、Paolo Cavanni、Susanna Cremonesi、Michele Dal Cin、Aldo Feriani、Beatrice Oliosi、Teresa Semeraro、Luca Tarsi、Silvia Tomelleri、Andrea Wong、Filippo Visentini、Laura Zonzini、Christian Heidbreder

  DOI：10.1016/j.bmc.2016.02.031

  日期：2016.4

  high affinity and selectivity at the DA D3 receptor is reported here. Compounds endowed with high selectivity over the hERG channel were identified and their pharmacokinetic properties thoroughly analyzed. A few derivatives with appropriate developability characteristics were selected for further studies and progression along the screening cascade. In particular, derivative 60a, (DA D3 pKi = 8.4, DA D2

  本文报道了一系列新的1,2,4-三唑基八氢吡咯并[2,3- b ]吡咯在DA D3受体上表现出高亲和力和选择性。鉴定了在hERG通道上具有高选择性的化合物，并对其药代动力学特性进行了全面分析。选择了一些具有适当可显影性的衍生物，以进一步研究并沿着筛选级联进行。特别地，衍生物60a（DA D3 p K i  ＝ 8.4，DA D2 p K i  ＝ 6.0和hERG fp K i  ＝ 5.2）显示出平衡的分布，并且围绕该分子进行进一步的改进。
• [EN] cGAS ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DU CGAS
  申请人：IMMUNE SENSOR LLC

  公开号：WO2017176812A1

  公开（公告）日：2017-10-12

  Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

  揭示了一种新型化合物的化学式（I），这些化合物是cGAS拮抗剂，涉及到这些化合物的制备方法、包含这些化合物的药物组合物，以及它们在医学治疗中的应用。
• [EN] MACROCYCLIC BROAD SPECTRUM ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES MACROCYCLIQUES À LARGE SPECTRE
  申请人：RQX PHARMACEUTICALS INC

  公开号：WO2018149419A1

  公开（公告）日：2018-08-23

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of bacterial type 1 signal peptidase (SpsB), an essential protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本文提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌类型1信号肽酶（SpsB）发挥作用，这是细菌中的一种必需蛋白质。还提供了使用所述化合物的药物组合物和治疗方法。
• [EN] COMBINATION PHARMACEUTICAL AGENTS AS RSV INHIBITORS<br/>[FR] AGENTS PHARMACEUTIQUES EN COMBINAISON EN TANT QU'INHIBITEURS DE RSV
  申请人：ENANTA PHARM INC

  公开号：WO2019067864A1

  公开（公告）日：2019-04-04

  The present invention relates to pharmaceutical agents administered to a subject either in combination or in series for the treatment of a Respiratory Syncytial Virus (RSV) infection, wherein treatment comprises administering a compound effective to inhibit the function of the RSV and an additional compound or combinations of compounds having anti-RSV activity.

  本发明涉及用于治疗呼吸道合胞病毒（RSV）感染的药物剂，该药物剂可以单独或连续给予受试者，治疗包括给予一种有效抑制RSV功能的化合物以及具有抗RSV活性的另一种化合物或化合物组合。