4-甲酸苯基三氟硼酸钾 | 374564-36-0

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟硼酸钾系列
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲酸苯基三氟硼酸钾
• 中文别名: (4-甲酰基苯基)三氟硼酸钾
• 英文名称: potassium 4-formylphenyltrifluoroborate
• 英文别名: potassium;trifluoro-(4-formylphenyl)boranuide
• CAS: 374564-36-0
• 化学式: C₇H₅BF₃O*K
• mdl: MFCD02093980
• 分子量: 212.021
• InChiKey: PEWVRVCGAOIWBB-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(lit.)
• 稳定性/保质期：

  避免与氧化物、高温、热量和光线接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  13
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  保存方法：将物品存放在密闭、阴凉、通风且干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Potassium (4-formylphenyl)trifluoroborate
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: Potassium (4-formylphenyl)trifluoroborate
CAS number: 374564-36-0

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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: C7H5BF3KO
Molecular weight: 212.0

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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：

  4-甲酸苯基三氟硼酸钾 在 Oxone 、 水 作用下， 以 丙酮 为溶剂， 反应 0.03h， 以99%的产率得到对羟基苯甲醛
  参考文献：
  名称：

  Oxidation of Organotrifluoroborates via Oxone

  摘要：

  A method for the oxidation of organotrifluoroborates using Oxone was developed. A variety of aryl-, heteroaryl-, alkenyl-, and alkyltrifluoroborates were converted into the corresponding oxidized products in excellent yields. This method proved to be tolerant of a broad range of functional groups, and in secondary alkyl substrates it was demonstrated to be completely stereospecific.

  DOI：

  10.1021/jo102208d
• 作为产物：
  描述：

  4-甲酰基苯硼酸 在 二氟化氢钾 作用下， 以 甲醇 、 水 为溶剂， 以92%的产率得到4-甲酸苯基三氟硼酸钾
  参考文献：
  名称：

  一些有机三氟硼酸钾的 (1)H、(13)C、(19)F 和 (11)B NMR 光谱参考数据。

  摘要：

  描述了 28 种有机三氟硼酸钾的完整 (1)H、(13)C、(19)F 和 (11)B NMR 光谱数据。大多数研究的化合物都描述了带有硼原子的碳的共振。使用修改后的 (11)B NMR 脉冲序列并观察到更好的分辨率，允许观察一些研究化合物的 (11)B-(19)F 耦合常数。

  DOI：

  10.1002/mrc.2467

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。
• Hydrogen‐Bond‐Donor Solvents Enable Catalyst‐Free (Radio)‐Halogenation and Deuteration of Organoborons
  作者：Yi Yang、Xinyan Gao、Xiaojun Zeng、Junbin Han、Bo Xu

  DOI：10.1002/chem.202003919

  日期：2021.1.18

  A hydrogen bond donor solvent assisted (radio)halogenation and deuteration of organoborons has been developed. The reactions exhibited high functional group tolerance and needed only an ambient atmosphere. Most importantly, compared to literature methods, our conditions are more consistent with the principals of green chemistry (e.g., metal‐free, strong oxidant‐free, more straightforward conditions)

  已经开发了氢键供体溶剂辅助的有机硼的（放射性）卤化和氘代。该反应表现出高的官能团耐受性并且仅需要环境气氛。最重要的是，与文献方法相比，我们的条件与绿色化学原理更加一致（例如，无金属，无强氧化剂，更简单的条件）。
• Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide
  作者：Min-Liang Yao、George W. Kabalka、David W. Blevins、Marepally Srinivasa Reddy、Li Yong

  DOI：10.1016/j.tet.2012.03.016

  日期：2012.5

  Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-brom

  报道了在水介质中使用市售的三溴化四丁基铵（TBATB）或三碘化铯对有机三氟硼酸盐进行卤代硼烷化。事实证明，这种温和的不含过渡金属的方法可耐受多种官能团。观察到高的区域选择性和化学选择性。两个合成路线（ż）从炔-dibromoalkenes，通过stereodefined（ż）-2- bromoalkenyltrifluoroborates和（Ž）-1,2-双（硼烷基）alkenyltrifluoroborates，已经使用TBATB介导bromodeboronation作为关键步骤开发的。
• Pd-Catalyzed Remote <i>Meta-</i>C–H Functionalization of Phenylacetic Acids Using a Pyridine Template
  作者：Zhong Jin、Ling Chu、Yan-Qiao Chen、Jin-Quan Yu

  DOI：10.1021/acs.orglett.7b03336

  日期：2018.1.19

  An effective pyridine based U-shaped template has been developed to enable a diverse range of meta-C–H functionalizations of phenylacetic acid scaffolds. This new template has extended the reaction scope to cross-coupling with ArBF3K as well as iodination using 1,3-diiodo-5,5-dimethylhydantoin as the iodination reagent.

  已开发出一种有效的基于吡啶的U形模板，可实现苯乙酸支架的多种间位-C–H官能化。该新模板将反应范围扩展到与ArBF 3 K交叉偶联以及使用1,3-二碘-5,5-二甲基乙内酰脲作为碘化试剂的碘化反应。
• Nickel-Catalyzed Borylation of Halides and Pseudohalides with Tetrahydroxydiboron [B₂(OH)₄]
  作者：Gary A. Molander、Livia N. Cavalcanti、Carolina García-García

  DOI：10.1021/jo401104y

  日期：2013.7.5

  with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the

  芳基硼酸作为试剂和目标结构在各种有用的应用中变得越来越重要。最近，报道了使用原子经济的四羟基二硼（BBA）试剂在钯催化下合成芳基硼酸。钯的高成本，加上钯和铜催化工艺的一些限制，促使我们开发一种替代方法。因此，已经制定了使用四羟基二硼（BBA）对芳基和杂芳基卤化物和拟卤化物进行镍催化的硼基化反应。该反应被证明具有广泛的官能团耐受性并适用于许多杂环体系。据我们所知，这里提供的例子代表了在室温下进行的唯一有效的镍催化宫浦硼化反应。