2-羟基-4-吡啶醛 | 188554-13-4

• 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: 2-羟基-4-吡啶醛
• 中文别名: 2-羟基吡啶-4-甲醛；2-羟基异烟醛
• 英文名称: 2-hydroxy-4-formylpyridine
• 英文别名: 2-hydroxypyridine-4-carbaldehyde；2-hydroxypyridine-4-carboxaldehyde；2-hydroxyisonicotinaldehyde；2-hydroxyisonotinaldehyde；2-oxo-1,2-dihydropyridine-4-carbaldehyde；2-hydroxy-4-pyridinecarboxaldehyde；2-hydroxypyridine 4-aldehyde；2-oxo-1H-pyridine-4-carbaldehyde
• CAS: 188554-13-4
• 化学式: C₆H₅NO₂
• mdl: MFCD03788455
• 分子量: 123.111
• InChiKey: IDDXMCNSHNXTRS-UHFFFAOYSA-N

物化性质

• 熔点：
  79-81 °C
• 沸点：
  333.7±42.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37
• 危险类别码：
  R43,R36,R22
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H317,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Hydroxy-4-pyridinecarboxaldehyde
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H317: May cause an allergic skin reaction
H319: Causes serious eye irritation
P280: Wear protective gloves/protective clothing/eye protection/face protection
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Hydroxy-4-pyridinecarboxaldehyde
CAS number: 188554-13-4

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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.
Storage: Store in closed vessels, refrigerated.

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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
No data
Boiling point:
Melting point: No data
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

2-羟基-4-吡啶醛是一种有机中间体，可通过将2-羟基-4-甲基吡啶与二氧化硒反应制得。该化合物可用于制备一种ROR-γ调节剂。

制备

在氩气保护下，向无水二恶烷（35 mL）中加入2-羟基-4-甲基吡啶（2.10 g，19.2 mmol）和二氧化硒（2.50 g，22.5 mmol）。将混合物回流48小时。冷却至室温后，使用碳酸氢钠（1.5 g）中和酸性副产物，并搅拌3小时。通过过滤除去不溶性残留物，依次使用硫酸镁（2.5 g）、弗洛里西（2.5 g）和硅藻土（2.5 g）作为垫层。真空浓缩黄色滤液，得到粗化合物（1.40 g）。通过硅胶柱色谱法，在乙酸乙酯和9：1乙酸乙酯/甲醇中纯化粗产物，最终获得2-羟基-4-吡啶醛。

反应信息

• 作为反应物：
  描述：

  2-羟基-4-吡啶醛 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 selenium(IV) oxide 、 sodium ethanolate 、 lithium chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 生成 2-[(1E,3E,5E,7E)-2,6-dimethyl-8-(2,6,6-trimethylcyclohex-1-en-1-yl)octa-1,3,5,7-tetraen-1-yl]-4-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hexa-1,3,5-trien-1-yl]pyridine
  参考文献：
  名称：

  Fluorescent pigments of the retinal pigment epithelium and age-related macular degeneration

  摘要：

  The major hydrophobic fluorophore of the retinal pigment epithelium (RPE) is A2E, a pyridinium bis-retinoid derived from all-trans-retinal and phosphatidyl-ethanolamine. The accumulation of fluorophores such as A2E is implicated in the pathogenesis of age-related macular degeneration (AMD), a disease associated with the deterioration of central vision and a leading cause of blindness in the elderly. Recent chemical and biological studies have provided insight into the synthesis and biosynthesis of A2E, the spectroscopic properties of this pigment, and the role of A2E and RPE cell death. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00314-6
• 作为产物：
  描述：

  2-羟基-4-甲基吡啶 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以52%的产率得到2-羟基-4-吡啶醛
  参考文献：
  名称：

  眼龄色素 A2-E 的全合成：收敛途径

  摘要：

  随着年龄的增长，在人视网膜色素上皮 (RPE) 细胞中积累的自发荧光年龄色素 (脂褐素) 被认为是导致各种眼病的原因，包括与年龄相关的黄斑变性 (AMD)，这是老年人失明的主要原因1 在 40 岁以上的美国人中，与 AMD 相关的患病率估计为 9.2%，2 并且预计随着中位年龄的增加，AMD 的发病率将呈上升趋势。RPE 中脂褐素积累的性质仍然是个谜。据认为，色素是溶酶体中吞噬细胞外段圆盘未完全消化而产生的累积碎片，其中包含自发荧光的类视色素。 3 其中，橙色荧光团引起了广泛的兴趣，因为它们暗示与年龄相关的感光细胞功能下降有关。通过 2 当量的视黄醛（维生素 A）和 1 当量的乙醇胺（因此名称为“A2-E”）的仿生反应，最初分配给从 250 多只供体眼中分离的主要橙色荧光团的结构已修改为 1（方案 1） ”；经过广泛色谱分析后的产率为 0.5%）和结构研究。5 应注意这种两亲化合物前所未有的楔形形状（方案

  DOI：

  10.1021/ja9700414

文献信息

• [EN] PYRAZOLOPYRIMIDINES AS CYCLIN-DEPENDENT KINASE INHIBITORS<br/>[FR] PYRAZOLOPYRIMIDINES TENANT LIEU D'INHIBITEURS DE KINASES DEPENDANTES DE LA CYCLINE
  申请人：SCHERING CORP

  公开号：WO2004022561A1

  公开（公告）日：2004-03-18

  In its many embodiments, the present invention provides a novel class of pyrazolo[1,5-a]pyrimidine compounds as inhibitors of cyclin dependent kinases, methods of preparing such compounds, pharmaceutical compositions containing one or more such compounds, methods of preparing pharmaceutical formulations comprising one or more such compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the CDKs using such compounds or pharmaceutical compositions.

  在其多种实施方式中，本发明提供了一类新型的吡唑并[1,5-a]嘧啶化合物，作为细胞周期依赖性激酶的抑制剂，以及制备这类化合物的方法，含有一种或多种这类化合物的药物组合物，制备包含一种或多种这类化合物的药物配方的方法，以及利用这类化合物或药物组合物治疗、预防、抑制或改善与CDKs相关的一种或多种疾病的方法。
• [EN] SUBSTITUTED 3-AMINO-THIENO[2,3-B] PYRIDINE-2-CARBOXYLIC ACID AMIDE COMPOUNDS AS IKK INHIBITORS<br/>[FR] COMPOSES AMIDE D'ACIDE 3-AMINO-THIENO[2,3-B] PYRIDINE-2-CARBOXYLIQUE SUBSTITUE SERVANT D'INHIBITEURS D'IKK
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2005056562A1

  公开（公告）日：2005-06-23

  Disclosed are compounds of formula (I): wherein the variables R1, R2, R3 and Z are described herein, which are useful as inhibitors of the kinase activity of the IκB kinase (IKK) complex. The compounds are therefore useful in the treatment of IKK mediated diseases including autoimmune diseases inflammatory diseases and cancer. Also disclosed are pharmaceutical compositions comprising these compounds and processes for preparing these compounds.

  披露了公式(I)的化合物：其中变量R1、R2、R3和Z如本文所述，它们作为IκB激酶(IKK)复合物的激酶活性的抑制剂是有用的。因此，这些化合物在治疗IKK介导的疾病，包括自身免疫性疾病、炎症性疾病和癌症方面是有用的。还披露了包含这些化合物的药物组合物以及制备这些化合物的方法。
• [EN] SUBSTITUTED 1,1'-BIPHENYL COMPOUNDS AND METHODS USING SAME<br/>[FR] COMPOSÉS 1,1'-BIPHÉNYLE SUBSTITUÉS ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ARBUTUS BIOPHARMA INC

  公开号：WO2021158481A1

  公开（公告）日：2021-08-12

  The present invention includes substituted 1,1'-biphenyl compounds, analogues thereof, and compositions comprising the same. In one aspect, the compounds contemplated in the invention can be used to treat, ameliorate, or prevent hepatitis B virus (HBV) and/or hepatitis D virus (HDV) infections in a patient. In another aspect, the compounds contemplated in the invention can be used to treat, ameliorate, and/or prevent cancer in a patient.

  本发明包括取代的1,1'-联苯化合物，其类似物，以及包含它们的组合物。在一个方面，本发明中考虑的化合物可用于治疗、改善或预防患者体内的乙型肝炎病毒（HBV）和/或丙型肝炎病毒（HDV）感染。在另一个方面，本发明中考虑的化合物可用于治疗、改善和/或预防患者体内的癌症。
• DNA-cleaving antitumor agents
  申请人：——

  公开号：US20020132797A1

  公开（公告）日：2002-09-19

  A chemical composition and method of use of the composition is described. The chemical composition includes an aza-enediyne, aza-enyne allene, or an aza-diallene. These compound are preferably non-hydrolyzable, cationic compounds that bind to nucleic acids. In addition it is believed that these compounds may undergo chemical reactions in the presence of a nucleic acid to generate reactive intermediates that cleave nucleic acids.

  描述了一种化学组合物及其使用方法。该化学组合物包括一种氮杂-烯二炔、氮杂-烯炔丙烯或氮杂-二烯。这些化合物最好是不易水解的、阳离子化合物，能够结合到核酸上。此外，据信这些化合物在核酸存在的情况下可能会发生化学反应，产生能够切割核酸的活性中间体。
• [EN] HETEROARYL SUBSTITUTED BETA-HYDROXYETHYLAMINES FOR USE IN TREATING HYPERGLYCAEMIA<br/>[FR] BÊTA-HYDROXYÉTHYLAMINO SUBSTITUÉES PAR HÉTÉROARYLE DESTINÉES À ÊTRE UTILISÉES DANS LE TRAITEMENT DE L'HYPERGLYCÉMIE
  申请人：ATROGI AB

  公开号：WO2019053427A1

  公开（公告）日：2019-03-21

  There is herein provided a compound of formula (I) or a pharmaceutically acceptable salt thereof,wherein the ring containing Q1to Q5, and the groups R1, R2 and R3, have meanings as provided in the description.

  本文提供了一个式(I)的化合物或其药用可接受的盐，其中环含有Q1至Q5，以及基团R1、R2和R3的含义如描述中所提供。