(3,5-二氟苯基)三氟硼酸钾 | 267006-26-8

• 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: (3,5-二氟苯基)三氟硼酸钾
• 英文名称: potassium 3,5-difluorophenyl-trifluoroborate
• 英文别名: Potassium (3,5-difluorophenyl)trifluoroborate；potassium;(3,5-difluorophenyl)-trifluoroboranuide
• CAS: 267006-26-8
• 化学式: C₆H₃BF₅*K
• 分子量: 219.991
• InChiKey: JFSPHPHYZHGKPO-UHFFFAOYSA-N

物化性质

• 熔点：
  273-278℃

计算性质

• 辛醇/水分配系数(LogP)：
  -0.98
• 重原子数：
  13
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 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
Potassium (3,5-difluorophenyl)trifluoroborate
Product Name:
Synonyms:

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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.
Potassium (3,5-difluorophenyl)trifluoroborate
Ingredient name:
CAS number: 267006-26-8

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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.

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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: C6H3BF5K
Molecular weight: 220.0

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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：

  苯乙醛酸钾盐 、 (3,5-二氟苯基)三氟硼酸钾 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 水 为溶剂， 反应 1.0h， 以74%的产率得到3,5-二氟苯甲酮
  参考文献：
  名称：

  在室温下水中 Ag（i）/过硫酸盐催化α-氧代羧酸盐与有机三氟硼酸盐的脱羧偶联†

  摘要：

  α-氧代羧酸盐和有机三氟硼酸盐的脱羧偶联反应在催化AgNO 3的存在下使用K 2 S 2 O 8作为氧化剂顺利进行，从而以高收率生成二芳基酮产物。该方法新颖，简单，安全，高效。芳基取代的α-氧代羧酸钾和有机三氟硼酸在室温下均能顺利进行。α-氧代羧酸盐作为酰化剂的利用表现出一些令人感兴趣的元素。

  DOI：

  10.1039/c7ra10924e
• 作为产物：
  描述：

  3,5-DIFLUOROPHENYLMAGNESIUM BROMIDE 在 硼酸三甲酯 、 盐酸 、 二氟化氢钾 作用下， 以 乙醚 、 甲醇 、 水 为溶剂， 以58%的产率得到(3,5-二氟苯基)三氟硼酸钾
  参考文献：
  名称：

  (Fluoroorgano)fluoroboranes and -fluoroborates I: synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes

  摘要：

  A convenient preparation of K[ArBF3] (Ar= 2-C6H4F, 3-C6H4F, 4-C6H4F, 2,6-C6H3F2, 3,5-C6H3F2, 2,4,6-C6H2F3, 3,4,5-C6H2F3, 2,3,4,5-C6HF4 and C6F5) is offered and the IR and multinuclear NMR spectra of these salts are reported. Treatment of the trifluoroborate salts with BF3 in chlorocarbon solvents provides an easy synthetic route to the corresponding aryldifluoroboranes ArBF2. The multinuclear NMR spectra of ArBF2 are presented. The electron substituent effect of the [-BF3](-)-group shows this substituent as one of the strongest sigma-electron donors, while its pi-electron influence is negligible (sigma(I) = - 0.32, sigma(R) = - 0.07). (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00690-7

文献信息

• 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，
• Total synthesis and dual PPARα/γ agonist effects of Amorphastilbol and its synthetic derivatives
  作者：Taejung Kim、Woojung Lee、Kyu Hyuk Jeong、Jung Ho Song、Soon-Hye Park、Pilju Choi、Su-Nam Kim、Seokjoon Lee、Jungyeob Ham

  DOI：10.1016/j.bmcl.2012.04.062

  日期：2012.6

  extract, is a biologically interesting natural trans-stilbene compound with dual peroxisome proliferator-activated receptor (PPAR) α/γ agonist activity. After total synthesis of APH-1 and its derivatives by Pd-catalyzed Suzuki–Miyaura cross-coupling of a common (E)-styryl bromide intermediate and various aromatic trifluoroborate compounds, we biologically evaluated APH-2–APH-12 for PPAR agonist activity

  Amorphastilbol（APH-1），从刺槐变种中分离。伞菌种子提取物，是一种生物学上有趣的天然反式二苯乙烯化合物，具有双重过氧化物酶体增殖物激活受体（PPAR）α/γ激动剂活性。一个共同的后通过Pd催化的铃木-宫浦APH-1及其衍生物的总合成的交叉偶联（É）-苯乙烯基溴化物中间体和各种芳族三氟硼酸盐化合物，我们对APH-2–APH-12的PPAR激动剂活性进行了生物学评估。与APH-1相比，APH-4和APH-11是有效的PPARα/γ转录激活因子。因此，我们建议APH-4和APH-11是新型的双重PPARα/γ激动剂，并可能通过增强葡萄糖和脂质代谢来治疗2型糖尿病。
• A modified procedure for the palladium catalyzed borylation/Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides utilizing bis-boronic acid
  作者：Gary A. Molander、Sarah L.J. Trice、Brittany Tschaen

  DOI：10.1016/j.tet.2015.04.026

  日期：2015.9

  A modified Pd-catalyzed method of forming aryl- and heteroarylboron species and a two-step, one-pot borylation/Suzuki-Miyaura cross coupling using the atom economical tetrahydroxydiboron (bis-boronic acid, BBA) is reported. By using ethylene glycol as an additive, the new method results in increased yields, lower BBA loading, faster reaction times, and a broader reaction scope, including previously

  报道了一种修饰的Pd催化的形成芳基和杂芳基硼物种的方法，以及使用经济的四羟基二硼原子（双硼酸，BBA）进行两步一锅的硼化/铃木-宫浦交叉偶联的方法。通过使用乙二醇作为添加剂，新方法可提高收率，降低BBA负载量，缩短反应时间并扩大反应范围，包括以前存在问题的底物，例如杂环化合物。
• New and Efficient Protocol for Arylation of Quinones
  作者：Oleg Demchuk、K. Pietrusiewicz

  DOI：10.1055/s-0028-1088118

  日期：2009.4

  A practical rhodium-mediated arylation of 1,4-quinones has been developed. The corresponding 2-aryl-1,4-quinones were obtained with excellent selectivity and high yields under convenient aerobic reaction conditions.

  已经开发出一种实用的铑催化芳基化1,4-喹诺酮的方法。在方便的有氧反应条件下，得到了相应的2-芳基-1,4-喹诺酮，具有优异的选择性和高产率。
• A Straightforward Approach to the Synthesis of Disubstituted Cyclopentenones
  作者：Mariane V. Roldão、Luis Gustavo Souza-Filho、Wanda P. Almeida、Fernando Coelho

  DOI：10.1002/ejoc.201901850

  日期：2020.3.22

  We describe an approach to prepare di‐substituted cyclopentenones with potential anti‐inflammatory activity, using MBH adducts as building blocks. The synthesis is based on a rhodium mediated 1,4‐addition and an intramolecular Friedel‐Crafts type reaction.

  我们描述了一种使用MBH加合物作为构建基来制备具有潜在抗炎活性的双取代环戊烯酮的方法。合成基于铑介导的1,4加成和分子内Friedel-Crafts型反应。