2,4,6-三溴-3-羟基吡啶 | 6602-34-2

• 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: 2,4,6-三溴-3-羟基吡啶
• 中文别名: 2,4,6-三溴吡啶-3-醇
• 英文名称: 2,4,6-tribromo-3-hydroxypyridine
• 英文别名: 2,4,6-tribromo-3-pyridinol；2,4,6-tribromo-pyridin-3-ol；2,4,6-Tribrom-pyridin-3-ol；2,4,6-Tribrom-3-hydroxy-pyridin；2,4,6-Tribromopyridin-3-ol
• CAS: 6602-34-2
• 化学式: C₅H₂Br₃NO
• 分子量: 331.789
• InChiKey: CJJDOBAYAHWINI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 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：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 2,4,6-Tribromo-3-pyridinol
Synonyms: 3-Hydroxy-2,,4,6-tribromopyridine

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 2,4,6-Tribromo-3-pyridinol
CAS number: 6602-34-2

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C5H2Br3NO
Molecular weight: 331.8

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,4,6-三溴-3-羟基吡啶 在 乙醇 、 一水合肼 作用下， 生成 2,4-二溴-5-羟基吡啶
  参考文献：
  名称：

  den Hertog et al., Recueil des Travaux Chimiques des Pays-Bas, 1950, vol. 69, p. 1281,1286

  摘要：

  DOI：
• 作为产物：
  描述：

  3-羟基吡啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 72.0h， 以96%的产率得到2,4,6-三溴-3-羟基吡啶
  参考文献：
  名称：

  N-溴代琥珀酰亚胺对活化吡啶的轻度区域选择性卤化

  摘要：

  已经研究了氨基、羟基和甲氧基吡啶（2-、3-和 4-取代）以及 2,6-二甲氧基吡啶与 N-溴代琥珀酰亚胺在不同溶剂中的区域选择性单卤化和二卤化反应。底物的反应性按氨基>羟基>甲氧基的顺序降低，区域选择性取决于取代基的位置（2-取代> 3-取代）。在大多数情况下，我们以区域选择性和高产率获得单溴化衍生物。羟基和氨基吡啶也可以用 2 当量的 NBS 以几乎定量的产率进行二溴化。

  DOI：

  10.1055/s-2001-18070

文献信息

• Synthesis of substituted pyrido-oxazepine-3-ols and benzo-oxazin-2-yl methanol via tandem epoxide opening and SNAr reaction
  作者：Shivaji Narayan Khadake、Mosim Amin Pathan、Faiz Ahmed Khan

  DOI：10.1016/j.tet.2023.133687

  日期：2023.11

  benzo-oxazin-2-yl methanol via tandem epoxide opening followed by SNAr reactions is reported. Oxirane derived from tribromopyridine undergoes epoxide opening followed by the SNAr reaction, yielding seven-membered pyrido-oxazepine-3-ols. Predominantly 2-cyclized pyrido-oxazepine-3-ols observed in this reaction. Oxirane derived from tribromonitrobenzene undergoes epoxide opening followed by SNAr reaction to produce

  报道了通过串联环氧化物开环然后进行 S N Ar反应合成吡啶并恶嗪-3-醇和苯并恶嗪-2-基甲醇的通用且无催化剂的方案。由三溴吡啶衍生的环氧乙烷经历环氧化物开环，然后进行SN Ar反应，产生七元吡啶并-氧杂氮杂-3-醇。在此反应中观察到主要是2-环化的吡啶并-氧杂氮杂-3-醇。由三溴硝基苯衍生的环氧乙烷经过环氧化物开环，然后进行SN Ar反应，生成六元苯并恶嗪-2-基甲醇。当环氧乙烷用伯胺处理时，主要形成2-环化苯并恶嗪-2-基甲醇。此外，用仲胺处理环氧乙烷会产生区域选择性的4-环化苯并恶嗪-2-基甲醇，并伴随脱烷基化。提出了一种合成苯并恶嗪-2-基甲醇的合理反应机制，该反应通过环氧化物开环和随后的 Smiles 重排进行。
• A Facile Procedure for Halodecarboxylation of Hydroxyaromatic Carboxylic Acids
  作者：Zhenbei Zhang、Olha Bakumenko、Feng Xue、Wenhui Sun、Zhishan Cao、Guisheng Zhang

  DOI：10.1055/a-2294-4029

  日期：——

  An efficient approach is reported for the direct halodecarboxylation of hydroxyaromatic acids by using a readily available N-halosuccinimide (halo = Cl, Br) as the sole promoter in ethanol at room temperature without any other catalyst or additive. This environmentally friendly route tolerates a wide substrate scope with good to excellent yields under convenient conditions.

  据报道，一种有效的方法是在室温下使用容易获得的N -卤代琥珀酰亚胺（卤素 = Cl、Br）作为乙醇中的唯一促进剂，在没有任何其他催化剂或添加剂的情况下，直接进行羟基芳香酸的卤代脱羧。这种环境友好的路线可耐受较宽的底物范围，在便利的条件下具有良好至优异的产量。
• Halogenation of Pyridinols using Bis(sym-collidine)iodine(I) and Bis(sym-collidine)bromine(I) hexafluorophosphate
  作者：Gérard Rousseau、Sylvie Robin

  DOI：10.1016/s0040-4039(97)00385-7

  日期：1997.4

  Iodination and bromination of pyridinols was achieved by action of the title reagents in methylene chloride. (C) 1997 Elsevier Science Ltd.
• DALLACKER F.; FECHTER P.; MUES V., Z. NATURFORSCH., 1979, B 34, NO 12, 1729-1736
  作者：DALLACKER F.、 FECHTER P.、 MUES V.

  DOI：——

  日期：——
• Mild Regioselective Halogenation of Activated Pyridines with N-Bromosuccinimide
  作者：Victoria Cañibano、Justo F. Rodríguez、Mercedes Santos、M. Ascensión Sanz-Tejedor、M. Carmen Carreño、Gema González、José L. García-Ruano

  DOI：10.1055/s-2001-18070

  日期：——

  and dihalogenations of amino, hydroxy and methoxy pyridines (2-, 3-, and 4-substituted) as well as 2,6-dimethoxy pyridine with N-bromosuccinimide in different solvents have been studied. Reactivity of the substrates decreases in the order amino>hydroxy>methoxy and regioselectivity depends on the position of the substituent (2-substituted > 3-substituted). In most of the cases we obtained monobrominated

  已经研究了氨基、羟基和甲氧基吡啶（2-、3-和 4-取代）以及 2,6-二甲氧基吡啶与 N-溴代琥珀酰亚胺在不同溶剂中的区域选择性单卤化和二卤化反应。底物的反应性按氨基>羟基>甲氧基的顺序降低，区域选择性取决于取代基的位置（2-取代> 3-取代）。在大多数情况下，我们以区域选择性和高产率获得单溴化衍生物。羟基和氨基吡啶也可以用 2 当量的 NBS 以几乎定量的产率进行二溴化。