3-溴-4-羟基-2(1H)-吡啶酮 | 96245-97-5

• 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: 3-溴-4-羟基-2(1H)-吡啶酮
• 中文别名: 2,4-二羟基-3-溴吡啶
• 英文名称: 3-bromo-2,4-dihydroxypyridine
• 英文别名: 3-Bromo-4-hydroxypyridin-2(1h)-one；3-bromo-4-hydroxy-1H-pyridin-2-one
• CAS: 96245-97-5
• 化学式: C₅H₄BrNO₂
• 分子量: 189.996
• InChiKey: AZYBXXIHALNBIX-UHFFFAOYSA-N

物化性质

• 熔点：
  263.5-264.5 °C (decomp)
• 沸点：
  298.2±40.0 °C(Predicted)
• 密度：
  2.044±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：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 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

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Bromopyridine-2,4-diol
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-Bromopyridine-2,4-diol
CAS number: 96245-97-5

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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: C5H4BrNO2
Molecular weight: 190.0

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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, hydrogen bromide.

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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-溴-4-羟基-2(1H)-吡啶酮 在 三溴氧磷 作用下， 生成 2,3,4-三溴吡啶
  参考文献：
  名称：

  den Hertog, Recueil des Travaux Chimiques des Pays-Bas, 1945, vol. 64, p. 85,98

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二羟基-3,5-二溴吡啶 在 sodium hydroxide 、 palladium on activated charcoal 作用下， 生成 3-溴-4-羟基-2(1H)-吡啶酮
  参考文献：
  名称：

  den Hertog; Schogt, Recueil des Travaux Chimiques des Pays-Bas, 1951, vol. 70, p. 353,359

  摘要：

  DOI：

文献信息

• Practical Pd/C-Catalysed Suzuki-Miyaura Reactions for the Preparation of 3-Aryl-4-oxypyridin-2(1<i>H</i>)-ones, 3-Aryl-2,4-oxypyridines and 3-Aryl-2,4-oxyquinolines as Useful Intermediates for the Synthesis of Biologically Active Compounds
  作者：Marc Lamblin、Hugo Bares、Jean Dessolin、Christel Marty、Nathalie Bourgougnon、François-Xavier Felpin

  DOI：10.1002/ejoc.201200721

  日期：2012.10

  4-oxypyridines, and 3-iodo-2,4-oxyquinolines with arylboronic acids are described as a useful and efficient alternative to homogeneous conditions. The methodology features ligand-free and environmentally friendly conditions, and tolerates a wide range of boronic acids. The cross-coupled products can be viewed as useful intermediates for the preparation of 3-aryl-4-hydroxypyridin-2(1H)-ones, which can be used

  3-iodo-4-oxypyridin-2(1H)-ones、3-iodo-2,4-oxypyridines 和 3-iodo-2,4-oxyquinolines 的实际多相 Pd/C 催化 Suzuki-Miyaura 交叉偶联反应芳基硼酸被描述为均相条件的有用且有效的替代方法。该方法的特点是无配体和环境友好的条件，并耐受广泛的硼酸。交叉偶联产物可被视为制备 3-芳基-4-羟基吡啶-2(1H)-酮的有用中间体，可用作抗疱疹剂的新核碱基。
• Synthesis, antitumor activity, and antiviral activity of 3-substituted 3-deazacytidines and 3-substituted 3-deazauridines
  作者：Dennis J. McNamara、P. Dan Cook、Lois B. Allen、Mary Jo Kehoe、Carolyn S. Holland、Annette G. Teepe

  DOI：10.1021/jm00169a032

  日期：1990.7

  independent synthesis, 1H NMR, and UV. Compounds 9a-f were devoid of activity against intraperitoneally implanted L1210 leukemia in mice. Compound 9f displayed significant activity against rhinovirus type 34 grown in WISH cells. 4-Amino-3-fluoro-1-beta-D-ribofuranosyl-2(1H)-pyridinone (1) displayed good activity against intraperitoneally implanted P388 leukemia in mice, but it was devoid of activity against

  4-氨基-1-β-D-呋喃呋喃糖基-2（1H）-吡啶酮（3-脱氮胞苷，3）和4-羟基-1-β-D-呋喃呋喃糖基-2（1H）-吡啶酮的新型3-取代类似物（3-deazauridine，4）已被合成并测试其抗肿瘤和抗病毒活性。因此，3的3-氯（9a），3-溴（9b）和3-硝基（9c）类似物以及3-氯（9d），3-溴（9e）和3-硝基（9f）类似物通过标准糖基化程序制备4个。通过卤化4-氨基-2（1H）来制备新型必需杂环4-氨基-3-氯-2（1H）-吡啶酮（7a）和4-氨基-3-溴-2（1H）-吡啶酮（7b） -吡啶酮（5）。必需的杂环化合物4-氨基-3-硝基-2（1H）-吡啶酮（7c），3-氯-4-羟基-2（1H）-吡啶酮（7d），3-溴-4-羟基-2（1H） -吡啶酮（7e），用已知方法由4-羟基-2（1H）-吡啶酮（6）合成4-羟基-3-硝基-2（1H）-吡啶酮（7f）。通过独立合成，1 H
• Collective Synthesis of 4-Hydroxy-2-pyridone Alkaloids and Their Antiproliferation Activities
  作者：Feiqing Ding、Min Li Leow、Jimei Ma、Ronny William、Hongze Liao、Xue-Wei Liu

  DOI：10.1002/asia.201402466

  日期：2014.9

  A collective synthesis of 4‐hydroxy‐2‐pyridone alkaloids—specifically, pretenellin B, prebassianin B, farinosone A, militarione D, pyridovericin, and torrubiellone C—has been achieved. Key steps include using a strategic convergent method to synthesize the densely substituted pyridone key intermediate by Suzuki–Miyaura cross‐coupling reaction, a divergent synthesis approach of target molecules by aldol

  已经实现了4-羟基-2-吡啶酮生物碱的集体合成，特别是pretenellin B，prebassianin B，farinosone A，militarione D，pyridovericin和torubibielloneC。关键步骤包括：使用战略收敛方法通过Suzuki-Miyaura交叉偶联反应合成密集取代的吡啶酮关键中间体，通过吡啶酮中间体与同源醛的醛醇缩合形成目标分子的发散方法，以及利用全反式多烯骨架。有趣的是，其中的六个肿瘤细胞系研究，torrubiellone下发现诱导对Jurkat T细胞有效的和凋亡抑制活性与IC 50个的值7.05μ中号。因此，这种方法可能潜在地促进了生物活性小分子文库的合成以及药物的发现。
• A Practical 2,3-Pyridyne Precursor
  作者：Michael A. Walters、Percy H. Carter、Satyajit Banerjee

  DOI：10.1080/00397919208021549

  日期：1992.11

  Abstract 3-Bromo-2-chloro-4-methoxypyridine has been developed as a practical 2,3-pyridyne precursor. The substituted 2,3-pyridyne generated from this precursor by halogen-metal exchange has been found to react regioselectively with 2-methoxyfuran and 2-methylfuran.

  摘要 3-溴-2-氯-4-甲氧基吡啶已被开发为实用的2,3-吡啶前体。已发现通过卤素-金属交换从该前体生成的取代的 2,3-吡啶可与 2-甲氧基呋喃和 2-甲基呋喃发生区域选择性反应。
• den Hertog et al., Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 673,690
  作者：den Hertog et al.

  DOI：——

  日期：——