2-溴吡啶-3-硼酸 | 452972-08-6

• 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-溴吡啶-3-硼酸
• 中文别名: 2-溴砒啶-3-硼酸
• 英文名称: 2-bromopyridin-3-ylboronic acid
• 英文别名: 2-bromo-3-pyridylboronic acid；dihydroxy(2-bromo-3-pyridyl)borane；2-Bromopyridine-3-boronic acid；(2-bromopyridin-3-yl)boronic acid
• CAS: 452972-08-6
• 化学式: C₅H₅BBrNO₂
• 分子量: 201.815
• InChiKey: ODWRFKJNUJLAHM-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C(dec.)
• 沸点：
  374.3±52.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  按规定使用和贮存不会分解，避氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 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：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
2-Bromopyridine-3-boronic acid
Product Name:
Synonyms: 2-Bromo-3-pyridineboronic acid; 2-Bromopyridin-3-ylboronic acid

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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-Bromopyridine-3-boronic acid
Ingredient name:
CAS number: 452972-08-6

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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, 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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C5H5BBrNO2
Molecular weight: 201.8

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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：

  2-溴吡啶-3-硼酸 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 2-(2-Bromo-pyridin-3-yl)-5-hydroxy-[1,3,2]dioxaborolan-4-one; compound with benzylamine
  参考文献：
  名称：

  吡啶基硼酸在Petasis硼酸曼尼希反应中的异常行为

  摘要：

  吡啶系列中Petasis硼酸曼尼希反应的实施使我们能够获得原始化合物，对其结构进行了研究并确定了二恶硼硼烷酮和胺的稳定配合物（1：1）。

  DOI：

  10.1016/j.tetlet.2006.01.115
• 作为产物：
  描述：

  2-溴-3-氨基吡啶 在 正丁基锂 、 氢溴酸 、 sodium nitrite 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 2-溴吡啶-3-硼酸
  参考文献：
  名称：

  新型卤代吡啶基硼酸和酯的合成。第2部分：2,4或5-卤代吡啶-3-基硼酸和酯

  摘要：

  本文描述了用于合成和5-卤代吡啶-3-基-硼酸酯的一般方法的新的2,4-隔离，或和4，7，10，13，15。这些化合物的制备考虑了使用n BuLi进行的区域选择性卤素-金属交换或区域选择性邻位交换-使用二异丙基氨基锂进行锂化，然后从适当的单或二卤代吡啶开始，用硼酸三异丙基酯淬灭。迄今为止研究的所有底物均提供单一的区域异构硼酸或酯产物。另外，已经发现这些化合物与一系列的芳基卤化物进行了Pd催化的偶联，并授权了一种制备新吡啶文库的策略。

  DOI：

  10.1016/s0040-4020(02)00283-1

文献信息

• Synthesis of fused 1,2-naphthoquinones with cytotoxic activity using a one-pot three-step reaction
  作者：Anton A. Nechaev、Pratap R. Jagtap、Ema Bažíková、Johana Neumannová、Ivana Císařová、Eliška Matoušová

  DOI：10.1039/d1ob00205h

  日期：——

  A method for the synthesis of fused 1,2-naphthoquinones, as analogues of biologically active natural terpene quinones, is described. The intermediate polycyclic naphthalenes were prepared by a one-pot palladium-catalysed process from simple alkynes, one of which was made from an optically pure biomass-derived levoglucosenone. The prepared methoxy-substituted naphthalenes were subsequently transformed

  描述了一种合成稠合 1,2-萘醌的方法，作为具有生物活性的天然萜醌的类似物。中间体多环萘是通过一锅钯催化工艺从简单的炔烃制备的，其中一种是由光学纯的生物质衍生的左旋葡糖烯酮制成的。制备的甲氧基取代的萘随后通过三价碘介导的氧化一步转化为 1,2-萘醌。发现萘醌产品具有细胞毒性。
• A Versatile, Electrophilic Reagent for Monofluoromethylthiolation^†
  作者：Rui Wang、Long Lu、Qilong Shen

  DOI：10.1002/cjoc.202300164

  日期：2023.9.15

  A new electrophilic monofluoromethylthiolating reagent N-fluoromethylthiophthalimide PhthSCH2F 1 was developed. Reagent 1 could be readily synthesized from easily available starting materials benzyl mercaptan and CH2FCl in three steps. N-Fluoromethylthiophthalimide 1 is a powerful electrophilic monofluoromethylthiolating reagent that allows the monofluoromethylthiolation of a wide range of nucleophiles

  开发了一种新型亲电单氟甲硫基化试剂N-氟甲硫基邻苯二甲酰亚胺PhthSCH 2 F 1 。试剂1可以由容易获得的起始原料苄硫醇和CH 2 FCl分三步容易地合成。N-氟甲基硫代邻苯二甲酰亚胺1是一种强大的亲电子单氟甲基硫基化试剂，可在温和条件下对多种亲核试剂进行单氟甲基硫基化，包括炔烃、芳基/乙烯基硼酸、富电子杂芳烃、β-酮酯和羟吲哚以及硫醇。