2-羟基苯基三氟硼酸钾 | 850313-92-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-羟基苯基三氟硼酸钾
• 中文别名: 2-羟基三氟硼酸钾
• 英文名称: potassium 2-hydroxyphenyltrifluoroborate
• 英文别名: potassium;trifluoro-(2-hydroxyphenyl)boranuide
• CAS: 850313-92-7
• 化学式: C₆H₅BF₃O*K
• 分子量: 200.01
• InChiKey: GNJVFVXTMQKQGP-UHFFFAOYSA-N

物化性质

• 熔点：
  >250 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -1.55
• 重原子数：
  12
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P305+P351+P338
• 危险性描述：
  H302,H315,H319
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Hydroxyphenyltrifluoroborate potassium salt
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: 2-Hydroxyphenyltrifluoroborate potassium salt
CAS number: 850313-92-7

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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, refrigerated.
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: C6H5BF3O.K
Molecular weight: 200.0

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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, hydrogen fluoride.

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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-羟基苯基三氟硼酸钾 在 四(三苯基膦)钯 、 dimethyl sulfide borane 、 potassium carbonate 、 双三氟甲烷磺酰亚胺 、 三乙胺 作用下， 以 甲醇 、 氟苯 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 36.0h， 生成 (2-羟基-[1,1'-联苯基]-3-基)三氟硼酸钾
  参考文献：
  名称：

  P-Directed Borylation of Phenols

  摘要：

  Internal borylation occurs upon activation of aryl di-isopropylphosphinite boranes with HNTf2 to give heterocyclic intermediates that can be reductively quenched to afford 6 or treated with KHF2 to give the phenolic potassium aryl trifluoroborate salts 10. The latter salts are useful for Pd-catalyzed coupling with aryl iodides under Molander conditions, provided that precautions are taken to remove the KNTf2 byproduct from the preceding KHF2 step.

  DOI：

  10.1021/ol303203m
• 作为产物：
  描述：

  2-溴苯酚 在 叔丁基锂 、 硼酸三异丙酯 、 potassium hydrogen difluoride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以21%的产率得到2-羟基苯基三氟硼酸钾
  参考文献：
  名称：

  A Facile One-Pot Preparation of Potassium Hydroxyaryl- and (Hydroxyalkyl)aryltrifluoroborates

  摘要：

  Potassium hydroxyaryl- and (hydroxyalkyl)aryltrifluoroborates have been prepared in a simple one-pot process from the corresponding hydroxy-substituted aryl halides in 51-98% yields through an in situ protection of the free hydroxyl group with t-BuLi. Also, we successfully performed a microwave-promoted Suzuki-Miyaura cross-coupling reaction of these substrates with aryl- and alkenyl bromides in the presence of 0.5 mol % of Pd(OAc)(2) catalyst without ligands.

  DOI：

  10.1021/ol800083j

文献信息

• Expanding the Balz-Schiemann Reaction: Organotrifluoroborates Serve as Competent Sources of Fluoride Ion for Fluoro-Dediazoniation
  作者：Tharwat Mohy El Dine、Omar Sadek、Emmanuel Gras、David M. Perrin

  DOI：10.1002/chem.201803575

  日期：2018.10.9

  The Balz–Schiemann reaction endures as a method for the preparation of (hetero)aryl fluorides yet is eschewed due to the need for harsh conditions or high temperatures along with the need to isolate potentially explosive diazonium salts. In a departure from these conditions, we show that various organotrifluoroborates (RBF3−s) may serve as fluoride ion sources for solution‐phase fluoro‐dediazoniation

  Balz-Schiemann反应作为一种制备（杂）芳基氟化物的方法而持久，但由于需要苛刻的条件或高温以及需要分离潜在爆炸性的重氮盐而被避开。与这些条件不同，我们显示了各种有机三氟硼酸盐（RBF 3 - s）可以作为氟离子源，用于在温和条件下在有机溶剂中进行溶液相氟脱氮。该方法成功地扩展到一锅法，避免了芳基重氮盐的分离。受阻位的（杂）苯胺在前所未有的温和条件下以良好至优异的产率进行氟化。综上所述，这项工作扩大了RBF 3的功能范围-在经典的Balz-Schiemann反应的更新中充当氟离子源。
• Scope of the Palladium-Catalyzed Aryl Borylation Utilizing Bis-Boronic Acid
  作者：Gary A. Molander、Sarah L. J. Trice、Steven M. Kennedy、Spencer D. Dreher、Matthew T. Tudge

  DOI：10.1021/ja303181m

  日期：2012.7.18

  wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic

  Suzuki-Miyaura 反应已成为合成有机化学家更有用的工具之一。直到最近，还没有直接的方法来制造偶联反应中最重要的成分，即硼酸。目前制造硼酸的方法通常使用苛刻或浪费的试剂来制备硼酸衍生物，并且需要额外的步骤来提供所需的硼酸。先前报道的钯催化的直接硼酸合成的范围被揭开，其中包括广泛的合成有用的芳基亲电试剂。它利用新推出的第二代 Buchwald XPhos 预制钯催化剂和双硼酸。为了便于隔离并保留通常敏感的 CB 键，
• Ruthenium-catalyzed regio- and site-selective <i>ortho</i> C–H borylation of phenol derivatives
  作者：Yuki Homma、Kazuishi Fukuda、Nobuharu Iwasawa、Jun Takaya

  DOI：10.1039/d0cc02889d

  日期：——

  Efficient synthesis of o-borylphenols is achieved through the Ru-catalyzed regio- and site-selective sp2 C–H borylation of aryl diphenylphosphinites followed by removal of the phosphorus directing group. A successful application to aryl phosphites enables practical one-pot borylation of phenols, demonstrating high synthetic utility of this protocol.

  通过Ru催化的芳基二苯基次膦酸酯的sp 2 C–H硼化，然后去除磷导向基团，可以实现邻硼烷基苯酚的高效合成。对芳基亚磷酸酯的成功应用使得苯酚可以进行实际的一锅法硼化，证明了该方案的高度合成效用。
• ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES
  申请人：Universal Display Corporation

  公开号：US20210399236A1

  公开（公告）日：2021-12-23

  Provided are organometallic compounds. Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.

  提供有机金属化合物。还提供了含有这些有机金属化合物的配方。进一步提供了利用这些有机金属化合物的OLED和相关消费品。
• Noncovalent inhibition of the serine proteases, α-chymotrypsin and trypsin by trifluoro(organo)borates
  作者：Reem Smoum、Abraham Rubinstein、Morris Srebnik

  DOI：10.1039/b415957h

  日期：——

  A series of potassium organotrifluoroborates were synthesized. Their stability to hydrolysis was determined in D2O, TRIS and phosphate buffer. It was found that in both D2O and TRIS buffers, these compounds are quite stable, whereas in phosphate buffer rapid hydrolysis occurs. Based on these results, a study was undertaken to determine whether potassium organotrifluoroborates can serve as protease inhibitors. It was found that potassium organotrifluoroborates increased inhibition by at least an order of magnitude over the corresponding boronates. Dixon plots showed that these compounds are reversible competitive inhibitors of α-chymotrypsin and trypsin. Based on 19F NMR, we speculate that they inactivate the enzymes as a result of the formation of hydrogen-bonds between fluorine atoms of the inhibitors and the serine protease.

  合成了一系列有机三氟硼酸钾。测定了它们在 D2O、TRIS 和磷酸盐缓冲液中的水解稳定性。结果发现，在 D2O 和 TRIS 缓冲液中，这些化合物都相当稳定，而在磷酸盐缓冲液中则会发生快速水解。基于这些结果，研究人员开始研究有机三氟硼酸钾是否可以作为蛋白酶抑制剂。研究发现，与相应的硼酸盐相比，有机三氟硼酸钾的抑制作用至少增加了一个数量级。狄克逊图显示，这些化合物是δ-糜蛋白酶和胰蛋白酶的可逆竞争抑制剂。根据 19F NMR，我们推测它们之所以能使酶失活，是因为抑制剂的氟原子与丝氨酸蛋白酶之间形成了氢键。