5-溴-2-羟基苯基硼酸 | 89598-97-0

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-溴-2-羟基苯基硼酸
• 中文别名: 5-溴-2-羟基苯硼酸
• 英文名称: (5-bromo-2-hydroxyphenyl)boronic acid
• 英文别名: 5-Bromo-2-hydroxyphenylboronic acid
• CAS: 89598-97-0
• 化学式: C₆H₆BBrO₃
• 分子量: 216.827
• InChiKey: XSXTWLOHAGPBNO-UHFFFAOYSA-N

物化性质

• 熔点：
  196-200
• 沸点：
  378.3±52.0 °C(Predicted)
• 密度：
  1.84±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.17
• 重原子数：
  11
• 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：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
5-Bromo-2-hydroxyphenylboronic acid
Product Name:
Synonyms: 2-Borono-4-bromophenol

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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.
5-Bromo-2-hydroxyphenylboronic acid
Ingredient name:
CAS number: 89598-97-0

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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.

---

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: C6H6BBrO3
Molecular weight: 216.8

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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, 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：

  5-溴-2-羟基苯基硼酸 以 二甲基亚砜 为溶剂， 反应 18.0h， 以92%的产率得到4-溴苯酚
  参考文献：
  名称：

  Protodeboronation of ortho- and para-Phenol Boronic Acids and Application to ortho and meta Functionalization of Phenols Using Boronic Acids as Blocking and Directing Groups

  摘要：

  The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by sigma-bond metathesis.

  DOI：

  10.1021/jo402174v
• 作为产物：
  描述：

  2-羟基苯硼酸 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 5-溴-2-羟基苯基硼酸
  参考文献：
  名称：

  芳基硼化合物-VIII：羟基和羧苯基硼酸的一些反应

  摘要：

  羧基和羟基苯基硼酸（I-VI）的一些新的衍生物已被制备并直接卤化邻位和对位羟基和甲氧基苯基酸进行了研究。

  DOI：

  10.1016/s0040-4020(01)99333-0

文献信息

• One-Pot Generation of Functionalized Benzynes from Readily Available 2-Hydroxyphenylboronic Acids
  作者：Takashi Ikawa、JingKai Sun、Akira Takagi、Shuji Akai

  DOI：10.1021/acs.joc.9b03169

  日期：2020.3.6

  We developed a one-pot method for the generation of benzynes from a range of readily available 2-hydroxyphenylboronic acids. This method features the in situ activation of both boronic acid and hydroxyl groups of the substrate to enhance benzyne generation at 60 °C. Such mild conditions facilitate the generation of functionalized benzynes that immediately react with diverse arynophiles to produce multisubstituted

  我们开发了一种一锅法，可从一系列容易获得的2-羟基苯基硼酸中生成苯炔。该方法的特点是原位活化硼酸和底物的羟基，以增强60°C下苯并炔的生成。这种温和的条件促进了官能化的苯并炔的生成，该苯并炔立即与各种亲核体反应生成多取代的稠合苯。
• 一种基于稠环呋喃的小分子材料制备方法及其应用
  申请人：中国科学院大学

  公开号：CN106883248A

  公开（公告）日：2017-06-23

  本发明属于分子材料技术领域，公开了一种基于稠环呋喃的小分子材料制备方法及其应用，包括：以2,3‑二溴呋喃、2,3‑二溴噻吩、2,3‑二溴硒吩、2,3‑二溴‑吲哚衍生物和2‑羟基苯硼酸衍生物为原料，经过铃木反应得到关键中间体；以亚铜或铜化合物为催化剂，1,10‑菲啰啉或联吡啶化合物为配体，发生分子内乌尔曼C‑O偶联反应，合成了一系列稠环呋喃类小分子材料。本发明底物的合成相对简单，产率高；呋喃成环反应时间大大缩短；亚铜化合物和联吡啶化合物为催化体系比较便宜；反应条件更温和；底物适用范围广；反应产率高，最高可达97%。因此该方法适合于工业化生产。
• Ullmann-Type Intramolecular C–O Reaction Toward Thieno[3,2-<i>b</i>]furan Derivatives with up to Six Fused Rings
  作者：Daoliang Chen、Dafei Yuan、Cheng Zhang、Hao Wu、Jianyun Zhang、Baolin Li、Xiaozhang Zhu

  DOI：10.1021/acs.joc.7b01745

  日期：2017.10.20

  A new strategy for the efficient synthesis of thieno[3,2-b]benzofuran derivatives (15 examples) was achieved on the basis of successive regioselective intermolecular Suzuki and newly developed intramolecular Ullmann C–O reactions in up to a 70% overall yield. The fast intramolecular C–O reaction can be realized by an efficient catalytic combination of CuI/1,10-phenanthroline in up to a 97% yield. This

  在连续的区域选择性分子间铃木和新开发的分子内Ullmann C–O反应的基础上，实现了高效率合成噻吩并[3,2- b ]苯并呋喃衍生物的新策略（15个实例），总收率高达70％。快速的分子内C-O反应可以通过CuI / 1,10-菲咯啉的有效催化组合实现，产率高达97％。该方法适用于构建高度稠合的含噻吩并[3,2 - b ]呋喃的杂环，包括DTBDF和TTDBF。C 8 -DTBDF单晶的π-π和氢键相互作用表明其在不久的将来应用OFET的巨大潜力。
• 含有氰基芳香基的化合物、其合成方法、有机材料、功能层和有机电致发光器件
  申请人：吉林奥来德光电材料股份有限公司

  公开号：CN113402525B

  公开（公告）日：2023-05-12

  本发明涉及有机合成技术领域，具体而言，涉及含有氰基芳香基的化合物、其合成方法、有机材料、功能层和有机电致发光器件。含有氰基芳香基的化合物的结构式如下所示：其中，Ar3表示为氰基或下述所示基团；其中，R1和R2分别独立的表示为连接键、氢原子、下述式3、下述式4和下述式5中的任意一种；其中，式(3)、式(4)和式(5)通过*所示碳位点与式(2)进行并环连接。其具有较高的玻璃化温度和分子热稳定性，合适的HOMO和LUMO能级，高电子迁移率，应用于OLED器件制作后，可有效提高器件的发光效率和使用寿命。
• Further investigation of inhibitors of MRSA pyruvate kinase: Towards the conception of novel antimicrobial agents
  作者：Christophe Labrière、Huansheng Gong、B. Brett Finlay、Neil E. Reiner、Robert N. Young

  DOI：10.1016/j.ejmech.2016.09.018

  日期：2017.1

  Several novel series of compounds were synthesized and evaluated as inhibitors of methicillin-resistant Staphylococcus aureus (MRSA) pyruvate kinase (PK). PK has been identified as a highly interconnected essential 'hub' protein in MRSA, with structural features distinct from the human homologs which makes it a novel antimicrobial target. Several MRSA PK inhibitors (including the hydrazide 1) were identified using in silico screening combined with enzyme assays and were found to be selective for bacterial enzyme compared to human PK isoforms. Structure-activity relationship (SAR) studies were carried out on the replacement of the hydrazide linker with 3-atoms, 2-atoms and 0-atom linkers and led us to discover more potent compounds with enzyme inhibiting activities in the low nanomolar range and some were found to effectively inhibit bacteria growth in culture with minimum inhibitory concentrations (MIC) as low as 1 mu g/mL. (C) 2016 Elsevier Masson SAS. All rights reserved.