2-氟苄基硼酸频哪醇酯 | 517920-60-4

• 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: 2-氟苄基硼酸频哪醇酯
• 英文名称: 2-(2-fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-fluorobenzylboronic acid pinacol ester；2-[(2-fluorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 517920-60-4
• 化学式: C₁₃H₁₈BFO₂
• 分子量: 236.094
• InChiKey: ABOCFFXSSUAFRP-UHFFFAOYSA-N

物化性质

• 沸点：
  271 °C
• 密度：
  1.04
• 闪点：
  118 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Fluorobenzylboronic acid pinacol ester
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-Fluorobenzylboronic acid pinacol ester
CAS number: 517920-60-4

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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, under −20◦C.
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: C13H18BFO2
Molecular weight: 236.1

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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-氟苄基硼酸频哪醇酯 在 palladium 10% on activated carbon 、 氢气 、 palladium diacetate 、 potassium carbonate 、 正丁基二(1-金刚烷基)膦 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 生成 methyl 7-(2-fluorobenzyl)-4-hydroxy-1-methylisoquinoline-3-carboxylate
  参考文献：
  名称：

  异喹啉酮类化合物及其应用

  摘要：

  本发明涉及一种异喹啉酮类化合物及其应用。具体来说，本发明涉及一种作为HIF脯氨酰羟化酶抑制剂的异喹啉酮类化合物及其药物组合物。而且，本发明还提供了上述异喹啉酮类化合物或其药物组合物在制备药物中的用途，所述药物用于预防或治疗与HIF相关或由HIF介导的疾病，例如贫血、缺血、局部缺血或缺氧等。

  公开号：

  CN108341777A
• 作为产物：
  描述：

  2-氟苯甲醛 在 水 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 13.0h， 生成 2-氟苄基硼酸频哪醇酯
  参考文献：
  名称：

  醛和酮的无金属直接脱氧硼酰化

  摘要：

  通过脱氧硼酸化将醛和酮直接转化为烷基硼酸酯是一种未知但非常理想的转化。在此，我们提出了一种在温和条件下进行羰基脱氧硼酰化的一步法和无金属方法。可以耐受多种芳香醛和酮，并成功转化为相应的苄基硼酸酯。通过与脂肪醛和酮相同的脱氧歧管，它还可以简明合成 1,1,2-三（硼酸酯），这是目前缺乏有效合成方法的化合物家族。鉴于其简单性和多功能性，我们预计这种新颖的硼酸化方法可以在有机硼合成中显示出巨大的前景，并在学术和工业环境中激发更多的羰基脱氧转化。

  DOI：

  10.1021/jacs.0c03813

文献信息

• Alkylboronic Esters from Copper-Catalyzed Borylation of Primary and Secondary Alkyl Halides and Pseudohalides
  作者：Chu-Ting Yang、Zhen-Qi Zhang、Hazmi Tajuddin、Chen-Cheng Wu、Jun Liang、Jing-Hui Liu、Yao Fu、Maria Czyzewska、Patrick G. Steel、Todd B. Marder、Lei Liu

  DOI：10.1002/anie.201106299

  日期：2012.1.9

  unprecedented copper‐catalyzed cross‐coupling reaction of the title compounds with diboron reagents is described (see scheme; Ts=4‐toluenesulfonyl). This reaction can be used to prepare both primary and secondary alkylboronic esters having diverse structures and functional groups. The resulting products would be difficult to access by other means.

  易于获得：描述了标题化合物与乙硼试剂的前所未有的铜催化交叉偶联反应（参见方案； Ts = 4-甲苯磺酰基）。该反应可用于制备具有不同结构和官能团的伯烷基硼酸酯和仲烷基硼酸酯。生成的产品将很难通过其他方式访问。
• PDE4 INHIBITOR
  申请人：SHIJIAZHUANG SAGACITY NEW DRUG DEVELOPMENT CO., LTD.

  公开号：US20190177318A1

  公开（公告）日：2019-06-13

  Provided are a PDE4 inhibitor and a use thereof in the preparation of a medicament for treating PDE4 related diseases. Specifically disclosed are the compound as shown in formula (I) and a pharmaceutically acceptable salt thereof.

  提供了一种PDE4抑制剂及其在制备用于治疗与PDE4相关疾病的药物中的用途。具体披露了如公式（I）所示的化合物及其药用可接受的盐。
• Photochemical Radical C–H Halogenation of Benzyl N‐Methyliminodiacetyl (MIDA) Boronates: Synthesis of α‐Functionalized Alkyl Boronates
  作者：Ling Yang、Dong‐Hang Tan、Wen‐Xin Fan、Xu‐Ge Liu、Jia‐Qiang Wu、Zhi‐Shu Huang、Qingjiang Li、Honggen Wang

  DOI：10.1002/anie.202011872

  日期：2021.2.15

  α‐haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C‐H halogenation of benzyl N‐methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C−Br bond in the brominated product could be readily transformed to a series of C−C

  α-卤代硼酸酯是有用的有机合成子，可以转化为多种α-取代的烷基硼。α-卤代硼酸酯的方法是有局限性的，通常会遇到苛刻的反应条件。本文报道的是苄基N-甲基亚氨基二乙酰基（MIDA）硼酸酯的光化学自由基CH卤化。通过使用该协议，氟化，氯化和溴化反应是有效的。与不同的亲核试剂反应后，溴化产物中的C-Br键可轻松转变为一系列C-C，C-O，C-N，CS，CP和C-I键，其中的α-卤代sp 2 -B硼酸酯很难伪造。发现了B（MIDA）部分的活化作用。
• 一种合成烷基硼酯化合物的方法
  申请人：苏州大学

  公开号：CN107903281B

  公开（公告）日：2019-10-29

  本发明公开了一种合成烷基硼酯化合物的方法，即以Fe(acac)3（acac=乙酰丙酮基）为单组份催化剂、在金属镁的存在下、通过氯代烷烃与联硼酸频那醇酯的交叉偶联反应合成烷基硼酯化合物的方法。本发明提供的合成烷基硼酯化合物的方法既避免了敏感金属有机试剂和多组份催化剂的使用，又实现了联硼酸频那醇酯的双边利用、显著减少了联硼酸频那醇酯的用量，在温和条件下可使价廉易得的氯代烷烃参与的偶联反应顺利进行；与文献报道的相比，具有更好的原子经济性、相当或更高的催化效率和更广的底物适用性。
• Pd0-mediated rapid coupling of methyl iodide with excess amounts of benzyl- and cinnamylboronic acid esters: efficient method for incorporation of positron-emitting 11C radionuclide into organic frameworks by coupling between two sp3-hybridized carbons
  作者：Hiroko Koyama、Zhouen Zhang、Ryosuke Ijuin、Siqin、Jeongwan Son、Yuma Hatta、Masashi Ohta、Masahiro Wakao、Takamitsu Hosoya、Hisashi Doi、Masaaki Suzuki

  DOI：10.1039/c3ra40815a

  日期：——

  Pd0-mediated rapid cross coupling between sp3-hybridized carbons of CH3I and benzyl- or cinnamylboronic acid esters using [PdP(tert-C4H9)3}2]/CsF in DMF/H2O gave the corresponding methylated compounds in high yield. The utility was well demonstrated for the synthesis of short-lived PET tracer, N-(4-[11C]ethylphenyl)propionamide, in 90 ± 1% radio-HPLC analytical yield and 49 ± 3% radiochemical yield

  钯0介导的SP之间的快速交叉耦合3个CH的杂化的碳原子3 I和苄基-或cinnamylboronic酸酯使用[钯P（叔-C 4 H ^ 9）3 } 2 ] / CSF在DMF /高氧2以高收率得到相应的甲基化化合物。证明该实用性可用于合成短寿命的PET示踪剂N-（4- [ 11 C]乙基苯基）丙酰胺，其放射HPLC分析产率为90±1％，放射化学产率为49±3％。