3-氟-4-联苯硼酸频哪醇酯 | 269410-15-3

• 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-氟-4-联苯硼酸频哪醇酯
• 中文别名: 2-氟-4-联苯硼酸频哪醇酯；2-(1,3-苯并噻唑-2-硫)丁二酸；2-氟-4-联苯硼酸频那醇酯
• 英文名称: 2-(2-fluoro-[1,1'-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-(2-fluoro-4-biphenylyl)-1,3,2-dioxaborolane；2-(2-fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-fluoro-4-biphenylylboronic acid pinacol ester；2-Fluoro-4-biphenylboronic acid, pinacol ester；2-(3-fluoro-4-phenylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 269410-15-3
• 化学式: C₁₈H₂₀BFO₂
• 分子量: 298.165
• InChiKey: OGXPMMGBQKEWBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Fluoro-4-biphenylboronic acid, pinacol ester
Synonyms: 2-(2-Fluorobiphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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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-Fluoro-4-biphenylboronic acid, pinacol ester
CAS number: 269410-15-3

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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: C18H20BFO2
Molecular weight: 298.2

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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：

  3-氟-4-联苯硼酸频哪醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium hydroxide 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(1-(4-chlorobenzyl)-5-(2-fluorobiphenyl-4-yl)-3-methyl-1H-indol-2-yl)-2,2-dimethylpropanoic acid
  参考文献：
  名称：

  Inhibitors of the inducible microsomal prostaglandin E2 synthase (mPGES-1) derived from MK-886

  摘要：

  A series of potent and selective inhibitors of the inducible microsomal PGE(2) synthase (mPGES-1) has been developed based on the indole FLAP inhibitor MK-886. Compounds 23 and 30 inhibit mPGES-1 with potencies in the low nanomolar range and with selectivities of at least 100-fold compared to their inhibition of mPGES-2, thromboxane synthase and binding affinity to FLAP. They also block the production of PGE(2) in cell based assays but with a decreased potency and more limited selectivity compared to the enzyme assays. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.027
• 作为产物：
  描述：

  4-溴-2-氟联苯 、 频那醇硼烷 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 66.0h， 生成 3-氟-4-联苯硼酸频哪醇酯
  参考文献：
  名称：

  Hydroboronation process

  摘要：

  该发明涉及合成芳基或烯烃硼酸酯的过程，包括以下反应：(i) 在烯烃化合物中的烯基取代位置具有卤素或类卤素取代基，或者(ii) 在芳香环中的环取代位置具有卤素或类卤素取代基，与二取代单氢硼烷在第8-11族金属催化剂存在下反应。该发明还涉及这些硼酸酯在偶联反应中的应用。该发明还涉及某些二取代单氢硼烷和芳基或烯烃硼酸酯。

  公开号：

  US06680401B1

文献信息

• Synthesis and Reactivity of α‐Cumyl Bromodifluoromethanesulfenate: Application to the Radiosynthesis of [ ¹⁸ F]ArylSCF ₃
  作者：Jiang Wu、Qunchao Zhao、Thomas C. Wilson、Stefan Verhoog、Long Lu、Véronique Gouverneur、Qilong Shen

  DOI：10.1002/anie.201813708

  日期：2019.2.18

  A highly reactive electrophilic bromodifluoromethylthiolating reagent, α-cumyl bromodifluoro-methanesulfenate 1, was prepared to allow for direct bromodifluoromethylthiolation of aryl boron reagents. This coupling reaction takes place under copper catalysis, and affords a large range of bromodifluoromethylthiolated arenes. These compounds are amenable to various transformations including halogen exchange

  制备了高反应性的亲电溴二氟甲基硫醇化试剂，α-枯基溴二氟甲基甲磺酸盐1，以允许芳基硼试剂的直接溴二氟甲基硫醇化。该偶联反应在铜催化下发生，并提供了大范围的溴二氟甲基硫醇化的芳烃。这些化合物可进行各种转化，包括与[18 F] KF / K222进行卤素交换，该过程可从相应的芳基硼酸频哪醇酯分两步获得[18 F]芳基SCF3。
• C(sp²)–H Borylation of Fluorinated Arenes Using an Air-Stable Cobalt Precatalyst: Electronically Enhanced Site Selectivity Enables Synthetic Opportunities
  作者：Jennifer V. Obligacion、Máté J. Bezdek、Paul J. Chirik

  DOI：10.1021/jacs.6b13346

  日期：2017.2.22

  Cobalt catalysts with electronically enhanced site selectivity have been developed, as evidenced by the high ortho-to-fluorine selectivity observed in the C(sp2)-H borylation of fluorinated arenes. Both the air-sensitive cobalt(III) dihydride boryl 4-Me-(iPrPNP)Co(H)2BPin (1) and the air-stable cobalt(II) bis(pivalate) 4-Me-(iPrPNP)Co(O2CtBu)2 (2) compounds were effective and exhibited broad functional

  已经开发出具有电子增强位点选择性的钴催化剂，在氟化芳烃的 C(sp2)-H 硼酸化中观察到的高邻位氟选择性证明了这一点。空气敏感的二氢化钴 (III) 硼基 4-Me-(iPrPNP)Co(H)2BPin (1) 和空气稳定的钴 (II) 双（新戊酸盐）4-Me-(iPrPNP)Co(O2CtBu) 2 (2) 化合物是有效的，并且在包含电子不同官能团的各种氟芳烃中表现出广泛的官能团耐受性，而不管芳烃上的取代模式如何。在苄基二甲胺和氢硅烷存在的情况下，钴催化剂观察到的电子增强的邻氟选择性得以保持，超过了贵金属催化剂观察到的已建立的定向基团效应。
• Iron-catalysed enantioselective Suzuki–Miyaura coupling of racemic alkyl bromides
  作者：Takahiro Iwamoto、Chiemi Okuzono、Laksmikanta Adak、Masayoshi Jin、Masaharu Nakamura

  DOI：10.1039/c8cc09523j

  日期：——

  facile access to various optically active α-arylpropionic acids including several nonsteroidal anti-inflammatory drugs (NSAIDs) of commercial importance. (R,R)-QuinoxP* is specifically able to induce chirality when compared to analogous P-chiral ligands that give racemic products, highlighting the critical importance of transmetalation in the present asymmetric cross-coupling system.

  已经开发出第一个铁催化的对映选择性的Suzuki-Miyaura偶联反应。在催化量的FeCl 2和（R，R）-QuinoxP *的存在下，芳基硼酸锂与α-溴丙酸叔丁酯以对映体会聚方式交叉偶联，从而可以轻松获得各种旋光性α-芳基丙酸，包括几种具有商业重要性的非甾体抗炎药（NSAIDs）。与产生外消旋产物的类似P-手性配体相比，（R，R）-QuinoxP *特别能够诱导手性，突出了在当前的不对称交叉偶联系统中金属转移的关键重要性。
• Oxidative Trifluoromethylation of Arylboronates with Shelf-Stable Potassium (Trifluoromethyl)trimethoxyborate
  作者：Bilal A. Khan、Annette E. Buba、Lukas J. Gooßen

  DOI：10.1002/chem.201102652

  日期：2012.2.6

  Introducing CF3: Arylboronic acid pinacol esters are converted into the corresponding benzotrifluorides with the easy‐to‐use one‐component trifluoromethylating reagent potassium (trifluoromethyl)trimethoxyborate, mediated by copper acetate under an oxygen atmosphere (see scheme).

  引入CF 3：芳氧硼酸频哪醇酯与易用的单组分三氟甲基化试剂（三氟甲基）三甲氧基硼酸钾在氧气气氛下通过乙酸铜转化为相应的苯并三氟化物（参见方案）。
• Copper-mediated pentafluoroethylation of organoboronates and terminal alkynes with TMSCF₃
  作者：Shitao Pan、Qiqiang Xie、Xiu Wang、Qian Wang、Chuanfa Ni、Jinbo Hu

  DOI：10.1039/d2cc00975g

  日期：——

  The TMSCF₃-derived CuCF₂CF₃ species has been successfully applied in pentafluoroethylation of organoboronates and terminal alkynes.

  TMSCF3衍生的CuCF2CF3物种已成功应用于有机硼酸酯和末端炔烃的五氟乙基化反应。