3-羟基吡啶-4-醛 | 1849-54-3

• 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-羟基吡啶-4-醛
• 中文别名: 3-羟基吡啶-4-甲醛
• 英文名称: 3-hydroxypyridine-4-carboxaldehyde
• 英文别名: 3-hydroxyisonicotinaldehyde；3-hydroxypyridin-4-carbaldehyde；3-hydroxy-4-pyridinecarboxaldehyde；3-Hydroxypyridin-4-aldehyd；4-formyl-3-hydroxypyridine；3-Hydroxypyridin-4-carboxaldehyd；3-hydroxypyridine-4-carbaldehyde；3-Hydroxy-4-formyl-pyridin
• CAS: 1849-54-3
• 化学式: C₆H₅NO₂
• mdl: MFCD01318565
• 分子量: 123.111
• InChiKey: NVLPDIRQWJSXLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128 °C
• 沸点：
  323.8±22.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 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：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  温度：2-8°C，保持在惰性气体氛围中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Hydroxypyridine-4-carboxaldehyde
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: 3-Hydroxypyridine-4-carboxaldehyde
CAS number: 1849-54-3

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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, refrigerated.
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: C6H5NO2
Molecular weight: 123.1

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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-羟基吡啶-4-醛是一种主要用于医药中间体的醛类有机化合物。

储存条件

该物质可在2-8°C，并在惰性气体氛围中保存。

应用

在有机化学的基础研究中，3-羟基吡啶-4-醛可用作合成有机配体的重要原料，用于修饰和合成吡啶类配体。通过对其不同官能团进行修饰，可以改变其电子性质及立体化学特性，进而调控合成的有机配体的性质。此外，该化合物还可以作为吡啶类底物，用于评估新开发合成方法的适用性和优化反应条件。

反应信息

• 作为反应物：
  描述：

  3-羟基吡啶-4-醛 在 肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到4-[(E)-[(E)-(3-hydroxypyridin-4-yl)methylidenehydrazinylidene]methyl]pyridin-3-ol
  参考文献：
  名称：

  Synthesis and spectroscopic properties of Schiff bases derived from 3-hydroxy-4-pyridinecarboxaldehyde

  摘要：

  A series of six new Schiff bases has been prepared by reacting aniline and 4-R-substituted anilines (R = CH3, OCH3, Br, Cl, NO2) with 3-hydroxy-4-pyridinecarboxaldehyde. The H-1, C-13, N-15 and O-17 NMR data of these compounds are used to discuss the tautomerism. N-15 NMR and O-17 NMR chemical shifts established the tautomer existing in solution as the hydroxy/imino. C-13 CPMAS NMR confirms that the same tautomer is found in the solid state. The stabilities of the tautomeric forms have been approached using density functional calculations (B3LYP/6-3IG**) in the gas phase. In all cases the neutral hydroxy/imino with E configuration is more stable than the oxo/enamino form (by similar to22 kJ mol(-1)) and significantly more stable than the betaine (by similar to75 kJ mol(-1)). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.10.036
• 作为产物：
  描述：

  3-甲氧基甲氧基吡啶 在 盐酸 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 生成 3-羟基吡啶-4-醛
  参考文献：
  名称：

  [EN] INHIBITORS OF THE KYNURENINE PATHWAY
  [FR] INHIBITEURS DE LA VOIE DE LA KYNURÉNINE

  摘要：

  本申请提供了吲哚胺2,3-双加氧酶-1和/或吲哚胺2,3-双加氧酶-2和/或色氨酸2,3-双加氧酶的新型抑制剂，以及它们的代谢物，以及药用可接受的盐或前药。还提供了制备这些化合物的方法。治疗有效量的一个或多个公式(I)的化合物可用于治疗由于色氨酸途径失调导致的疾病。公式(I)的化合物通过抑制吲哚胺2,3-双加氧酶-1和/或吲哚胺2,3-双加氧酶-2和/或色氨酸2,3-双加氧酶的酶活性或表达起作用。

  公开号：

  WO2014186035A1

文献信息

• Evaluation of 99mTc-labeled amino acids as radiopharmaceuticals. VI. N-pyridoxylidenehydrazine-N',N'-diacetic acid.
  作者：YOSHIKAZU MATSUSHIMA、SADAHIRO MORI、YOSHIHARU KARUBE、SETSURO SUGATA、AKIRA KONO、HARUKO KUNITOKU、YUZO YAMAMOTO、YOSHINORI MIYAKE、MASAHARU KOJIMA

  DOI：10.1248/cpb.32.2262

  日期：——

  ^<99m>Tc labeled N-pyridoxylidenehydrazine-N', N'-diacetic acid and related hydrazones were evaluated as hepatobiliary imaging agents. Hydrazones used in the study were N-pyridoxylidenehydrazine-N', N'-diacetic acid (PLHzDA), N-(3-hydroxy-4-pyridylmethylene) hydrazine-N', N'-diacetic acid (FHPHzDA), N-(4-pyridylmethylene) hydrazine-N', N'-diacetic acid (INHzDA), and N-pyridoxylidene-N', N'-dimethylhydrazine (PLDMHz). The hydrazones were labeled with 99mTc by the SnCl2 method and the 99mTc labeling was examined by thin-layer chromatography and high-performance liquid chromatography. 99mTc labeled hydrazones were administered to golden hamsters, and the distribution indicated that clearance occurred through the hepatobiliary system. Scintigraphic studies in rabbits indicated that 99mTc-labeled PLHzDA and FHPHzDA are useful hepatobiliary radiotracers.

  评估了^<99m>Tc标记的N-吡哆叉肼-N',N'-二乙酸及其相关腙作为肝胆显像剂的效果。研究中所用的腙包括：N-吡哆叉肼-N',N'-二乙酸（PLHzDA）、N-(3-羟基-4-吡啶亚甲基)肼-N',N'-二乙酸（FHPHzDA）、N-(4-吡啶亚甲基)肼-N',N'-二乙酸（INHzDA）和N-吡哆叉-N',N'-二甲基肼（PLDMHz）。这些腙通过SnCl2方法被标记为^<99m>Tc，其标记效果通过薄层色谱和高性能液相色谱进行检验。将^<99m>Tc标记的腙注射给金色仓鼠，分布研究表明其通过肝胆系统清除。在兔子上的闪烁成像研究表明，^<99m>Tc标记的PLHzDA和FHPHzDA是有效的肝胆放射性示踪剂。
• Novel cyclic urea derivatives, preparation thereof and pharmaceutical use thereof as kinase inhibitors
  申请人：AVENTIS PHARMA S.A.

  公开号：US20040248884A1

  公开（公告）日：2004-12-09

  The present invention relates to a cyclic urea compound of formula I: 1 as defined herein. The invention is also directed to the process for its preparation, pharmaceutical composition comprising it and its pharmaceutical use, as an inhibitor on a protein kinase. Thus, it is useful for preventing or treating a physiological disorder capable of being modulated by inhibiting the activity of a protein kinase, such as a solid tumor.

  本发明涉及一种如下式的环脲化合物： 1 如本文所定义。该发明还涉及其制备方法，包括它的药物组合物以及其作为蛋白激酶抑制剂的药用，因此，它对于预防或治疗能够通过抑制蛋白激酶活性而调节的生理紊乱是有用的，比如固体肿瘤。
• Studies on pyridoxine and pyridoxal analogs—I
  作者：Dietrich Heinert、Arthur E. Martell

  DOI：10.1016/s0040-4020(01)82610-7

  日期：1958.1

  reported. The preparation of the thio-semicarbazones of the aldehydes, as potential tuberculostatic agents, and of 3-hydroxy-4-hydroxymethylpyridine and 3-methoxy-4-hydroxymethylpyridine as pyridoxine analogs, are described.

  报道了3-羟基吡啶-2-醛，3-甲氧基吡啶-2-醛，3-羟基吡啶-4-醛，3-甲氧基吡啶-4-醛及其衍生物和一些新的中间体的制备，纯化和性质。描述了作为潜在的抗结核剂的醛的硫代半咔唑和作为吡pyr醇类似物的3-羟基-4-羟基甲基吡啶和3-甲氧基-4-羟基甲基吡啶的制备。
• [EN] PYRROLO[3,2-C]PYRIDIN-4-ONE DERIVATIVES USEFUL IN THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE PYRROLO[3,2-C]PYRIDIN-4-ONE UTILES DANS LE TRAITEMENT DU CANCER
  申请人：SCORPION THERAPEUTICS INC

  公开号：WO2022066734A1

  公开（公告）日：2022-03-31

  This disclosure provides chemical entities of Formula (I) (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/ or cocrystal, and/or drug combination of the compound) that inhibit epidermal growth factor receptor (EGFR, ERBB 1) and/or Human epidermal growth factor receptor 2 (HER2, ERBB2). These chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) EGFR and/or HER2 activation contributes to the pathology and/or symptoms and/or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also provides compositions containing the same as well as methods of using and making the same.

  本公开提供了化学实体的化学式(I)（例如，一种化合物或药用可接受的盐，和/或水合物，和/或共晶体，和/或该化合物的药物组合物），这些化学实体抑制表皮生长因子受体（EGFR，ERBB 1）和/或人表皮生长因子受体2（HER2，ERBB2）。这些化学实体可用于治疗某种情况、疾病或紊乱，其中增加（例如，过度）的EGFR和/或HER2激活导致该情况、疾病或紊乱的病理学症状和/或进展（例如，癌症）在一个受试者（例如，人类）中。本公开还提供含有相同化学实体的组合物，以及使用和制备这些组合物的方法。
• Syntheses of Chromenes and Azachromenes: 2<i>H</i>-1-Benzopyran, 2<i>H</i>-Pyrano[3,2-<i>b</i>]pyridine, 2<i>H</i>-Pyrano[2,3-<i>c</i>]pyridine, and Derivatives
  作者：Dominique Billeret、Dominique Blondeau、Henri Sliwa

  DOI：10.1055/s-1993-25962

  日期：——

  2H-1-Benzopyran and derivatives have been prepared by an intramolecular Wittig reaction in a heterogeneous medium starting from salicylaldehyde, (2-hydroxyalkyl)triphenylphosphonium salts, and potassium carbonate. Extension of this reaction to various o-hydroxyformylpyridines were performed in order to obtain 2H-pyrano[3,2-b]pyridine, 2H-pyrano[2, 3-c]pyridine, and derivatives.

  2H-1-Benzopyran 及其衍生物是由水杨醛、（2-羟基烷基）三苯基鏻盐和碳酸钾在异相介质中通过分子内 Wittig 反应制备的。将该反应扩展到各种邻羟基甲酰基吡啶，从而得到 2H-吡喃并[3,2-b]吡啶、2H-吡喃并[2,3-c]吡啶及其衍生物。