3-氟苯硼酸频哪醇酯 | 936618-92-7

• 物质功能分类: 有机原料 - 有机氟化合物 - 氟苯硼酸系列
• 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-氟苯硼酸频哪醇酯
• 中文别名: 3-氟苯硼酸频那醇酯
• 英文名称: 2-(3-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 3-fluorophenylboronic acid pinacol ester
• CAS: 936618-92-7
• 化学式: C₁₂H₁₆BFO₂
• 分子量: 222.067
• InChiKey: VWBPPYBBVMPZOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  286.6±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 3-Fluorophenylboronic acid pinacol ester
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 3-Fluorophenylboronic acid pinacol ester
CAS number: 936618-92-7

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C12H16BFO2
Molecular weight: 222.1

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-氟苯硼酸频哪醇酯 在 芘-1,6-二酮 、 氧气 、 异丙醇 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 以90%的产率得到3-氟苯酚
  参考文献：
  名称：

  yr酮作为通用的光催化剂，可在可见光下原位生成过氧化氢进行氧化反应。

  摘要：

  吡咯二酮（PYDs）是用于三种氧化反应的有效光催化剂：缺电子烯烃的环氧化，有机硼的氧化羟基化以及在可见光照射下通过原位生成H 2 O 2，使用氧作为末端氧化剂和IPA作为硫化物的氧化溶剂和氢供体。

  DOI：

  10.1039/c9gc03152a
• 作为产物：
  描述：

  3-氟苯磺酰氯 在 silver orthophosphate 、 碳酸氢钠 、 palladium dichloride 、 sodium sulfite 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 水 、 乙腈 为溶剂， 反应 20.0h， 生成 3-氟苯硼酸频哪醇酯
  参考文献：
  名称：

  通过 Pd 催化芳基亚磺酸钠与双（频哪醇）二硼的脱硫偶联反应合成芳基硼酸酯

  摘要：

  已经开发了在钯催化下芳基亚磺酸钠与双（频哪醇）二硼或双（新戊基乙醇基）二硼的脱硫硼化反应，允许选择性 CB 键形成，在温和的反应条件下以中等至良好的产率得到具有一系列官能团的芳基硼酸酯。克级制备以及芳基硼酸酯的级联 Suzuki-Miyaura 交叉偶联证明了在有机合成中的潜在实用价值。

  DOI：

  10.1016/j.tetlet.2021.153478

文献信息

• [EN] NEW THIENOPYRIMIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX DÉRIVÉS DE THIÉNOPYRIMIDINE, PROCÉDÉ POUR LEUR PRÉPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SERVIER LAB

  公开号：WO2015097123A1

  公开（公告）日：2015-07-02

  Compounds of formula (I): wherein R1, R2, R3, R4, R5, R6, R7, R12, X, A and n are as defined in the description.

  式（I）的化合物：其中R1、R2、R3、R4、R5、R6、R7、R12、X、A和n的定义如描述中所述。
• Visible Light-Induced Borylation of C–O, C–N, and C–X Bonds
  作者：Shengfei Jin、Hang. T. Dang、Graham C. Haug、Ru He、Viet D. Nguyen、Vu T. Nguyen、Hadi D. Arman、Kirk S. Schanze、Oleg V. Larionov

  DOI：10.1021/jacs.9b12519

  日期：2020.1.22

  photocatalytic borylation method that can effect borylation of a wide range of substrates, including strong C‒O bonds, remains elusive. Herein, we report a general, metal-free visible light-induced photocatalytic borylation platform that enables borylation of electron rich derivatives of phenols and anilines, chloroarenes, as well as other haloarenes. The reac-tion exhibits excellent functional group

  硼酸是中心重要的功能基序和合成前体。可见光诱导的硼酸化可以提供结构多样化的硼酸盐，但一种广泛有效的光催化硼酸化方法可以影响包括强 C-O 键在内的多种底物的硼化，仍然难以实现。在此，我们报告了一种通用的、无金属的可见光诱导光催化硼化平台，该平台能够对苯酚和苯胺、氯芳烃以及其他卤代芳烃的富电子衍生物进行硼化。该反应表现出优异的官能团耐受性，正如一系列结构复杂底物的硼化反应所证明的那样。值得注意的是，该反应是由吩噻嗪催化的，这是一种简单的有机光催化剂，MW< 200通过质子耦合电子转移机制介导了以前无法实现的可见光诱导的苯酚衍生物单电子还原，还原电位为~-3 V vs SCE。机理研究指出了光催化剂-碱相互作用的关键作用。
• Efficient metal-free photochemical borylation of aryl halides under batch and continuous-flow conditions
  作者：Kai Chen、Shuai Zhang、Pei He、Pengfei Li

  DOI：10.1039/c5sc04521e

  日期：——

  A rapid, chemoselective and metal-free C-B bond-forming reaction of aryl iodides and bromides in aqueous solution at low temperatures was discovered. This reaction is amenable to batch and continuous-flow conditions...

  发现了在低温下，水溶液中芳基碘化物和溴化物的快速，化学选择性和无金属的CB键形成反应。该反应适合间歇和连续流动条件...
• Redox-Neutral Borylation of Aryl Sulfonium Salts via C–S Activation Enabled by Light
  作者：Chen Huang、Jie Feng、Rui Ma、Shuaishuai Fang、Tao Lu、Weifang Tang、Ding Du、Jian Gao

  DOI：10.1021/acs.orglett.9b03850

  日期：2019.12.6

  photoinduced strategy for the borylation of aryl sulfonium salts using bis(pinacolato)diboron as the boron source. This method exploits redox-neutral aryl sulfoniums to gain access to aryl radicals via C-S bond activation upon photoexcitation under transition-metal-free conditions. Therefore, it grants access to diverse arylboronate esters with good performance from easily available aryl sulfoniums accompanied

  本文报道了一种使用双（频哪醇）二硼作为硼源进行芳基sulf盐的硼化的新光诱导策略。该方法利用氧化还原中性芳基sulf在无过渡金属条件下进行光激发时通过CS键活化来获得芳基自由基。因此，它可从容易获得的芳基sulf获得具有良好性能的各种芳基硼酸酯，并伴有温和的条件，操作简便和易于扩展。
• Synthesis of Pinacol Arylboronates from Aromatic Amines: A Metal-Free Transformation
  作者：Di Qiu、Liang Jin、Zhitong Zheng、He Meng、Fanyang Mo、Xi Wang、Yan Zhang、Jianbo Wang

  DOI：10.1021/jo3018878

  日期：2013.3.1

  A metal-free borylation process based on Sandmeyer-type transformation using arylamines derivatives as the substrates has been developed. Through optimization of the reaction conditions, this novel conversion can be successfully applied to a wide range of aromatic amines, affording borylation products in moderate to good yields. Various functionalized arylboronates, which are difficult to access by

  基于芳基胺衍生物作为底物的基于Sandmeyer型转化的无金属硼化工艺已得到开发。通过优化反应条件，这种新颖的转化方法可以成功地应用于各种芳族胺，从而以中等至良好的收率获得硼酸酯化产物。通过这种无金属的转化，可以容易地获得各种难以通过其他方法获得的官能化的芳基硼酸酯。此外，在不纯化硼酸酯化产物的情况下，Suzuki-Miyaura交叉偶联后即可进行这种转化，从而增强了该方法的实用性。已经提出了可能的涉及自由基物质的反应机理。