4-溴苯硼酸频那醇酯 | 68716-49-4

• 物质功能分类: 化学试剂 - 有机试剂 - 磺酸/亚磺酸
• 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-溴苯硼酸频那醇酯
• 中文别名: 1-溴-4-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯；4-溴苯硼酸频呐醇酯；2-(4-溴苯基)-4,4,5,5-四甲基-1,3,2-二氧环戊硼烷；4-溴苯硼酸频哪醇酯
• 英文名称: p-bromophenylboronic acid pinacol ester
• 英文别名: 2-(4-bromophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；4-bromophenylboronic acid pinacol ester；4-bromophenyl pinacol borane
• CAS: 68716-49-4
• 化学式: C₁₂H₁₆BBrO₂
• 分子量: 282.973
• InChiKey: AZCNDGAXOZWQPV-UHFFFAOYSA-N

物化性质

• 熔点：
  69.0 to 73.0 °C
• 沸点：
  324.1±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.75
• 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：
  2

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
• 储存条件：
  | 室温 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Bromophenylboronic acid, pinacol ester
Synonyms: 2-(4-Bromophenyl)-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: 4-Bromophenylboronic acid, pinacol ester
CAS number: 68716-49-4

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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, refrigerated.
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: C12H16BBrO2
Molecular weight: 283.0

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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 bromide.

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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-溴苯硼酸频那醇酯 在 tetrabutylammonium tetrafluoroborate 、 氧气 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 以83 %的产率得到4-溴苯酚
  参考文献：
  名称：

  无金属条件下芳基硼酸脱硼羟基化的电化学方法

  摘要：

  各种芳基硼的电化学脱硼羟基化已被很好地建立以在无金属条件下合成酚，其应用在药物合成和克级制备中得到突出。该协议具有简单的反应体系、良好的官能团耐受性和生态友好的反应条件。

  DOI：

  10.1002/asia.202200780
• 作为产物：
  描述：

  4-溴茴香硫醚 在 吡啶 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 24.0h， 生成 4-溴苯硼酸频那醇酯
  参考文献：
  名称：

  通过光激活的CS活化，芳基S盐的氧化还原中性硼化反应。

  摘要：

  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。

  DOI：

  10.1021/acs.orglett.9b03850
• 作为试剂：
  描述：

  苯甲腈 在 4-溴苯硼酸频那醇酯 作用下， 反应 4.0h， 生成 五氯苯甲腈
  参考文献：
  名称：

  多氯苯腈催化氟化制备多氟苯腈的方法

  摘要：

  本发明公开了多氯苯腈催化氟化制备多氟苯腈的方法，属于精细化工中间体制备领域。将氟化盐、有机溶剂和吸电子取代苯硼酸酯，加热活化反应；接着加入多氯苯腈，加热升温至80‑120℃，边反应边精馏，接着补加多氯苯腈和氟化钾，边反应边精馏，得到多氟苯腈。该反应体系催化活性高，解决活性较低单腈基类化合物，在氟化反应时转化率低/选择性中等的技术难点，在反应过程中通过边反应边将产品蒸馏出来的方式，促进了反应不断正向进行，提高了反应收率，非常容易进行工业化生产。

  公开号：

  CN111004149B

文献信息

• Rapid and Direct Photocatalytic C(sp ³ )−H Acylation and Arylation in Flow
  作者：Daniele Mazzarella、Antonio Pulcinella、Loïc Bovy、Rémy Broersma、Timothy Noël

  DOI：10.1002/anie.202108987

  日期：2021.9.20

  photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon-centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp3)−C(sp2) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced

  在此，我们报告了一种光催化程序，该程序可以使未官能化的烷基衍生物在流动中酰化/芳基化。该方法利用十钨酸盐阴离子作为氢原子提取物并产生亲核碳中心自由基的能力，这些自由基被镍催化剂拦截以最终形成 C(sp 3 )-C(sp 2 ) 键。由于流动条件的强化，反应时间可以从 12-48 小时减少到仅 5-15 分钟。最后，动力学测量强调了强化条件如何不改变反应机制，而是可靠地加速整个过程。
• Additive- and Photocatalyst-Free Borylation of Arylazo Sulfones under Visible Light
  作者：Yuliang Xu、Xinying Yang、Hao Fang

  DOI：10.1021/acs.joc.8b01662

  日期：2018.10.19

  developed a photocatalyst-free and additive-free, visible light induced borylation reaction using arylazo sulfones as starting material. This protocol shows some advantages such as mild conditions, simple equipment, and wide substrate scope, which gives a complementary protocol for the preparation of arylboronates.

  我们开发了一种以芳基偶氮砜为起始原料的无光催化剂和无添加剂的可见光诱导的硼酸酯化反应。该方案显示出一些优点，例如温和的条件，简单的设备和广泛的底物范围，为制备芳基硼酸酯提供了补充方案。
• Efficient Synthesis of Aryl Boronates via Zinc-Catalyzed Cross-Coupling of Alkoxy Diboron Reagents with Aryl Halides at Room Temperature
  作者：Shubhankar Kumar Bose、Todd B. Marder

  DOI：10.1021/ol502120q

  日期：2014.9.5

  A zinc(II)/NHC system catalyzes the borylation of aryl halides with diboron (4) reagents in the presence of KOMe at rt. This transformation can be applied to a broad range of substrates with high functional group compatibility. Radical scavenger experiments do not support a radical-mediated process.

  锌（II）/ NHC系统在室温下在KOMe存在下催化芳基卤化物与二硼（4）试剂的硼酸酯化反应。这种转变可应用于具有高官能团相容性的各种基材。自由基清除剂实验不支持自由基介导的过程。
• Arylsulfonyl fluoride boronic acids: Preparation and coupling reactivity
  作者：Terry Shing-Bong Lou、Michael C. Willis

  DOI：10.1016/j.tet.2019.130782

  日期：2020.1

  meta-isomers commence with the appropriate bromo-substituted benzenesulfonyl chlorides, and the ortho-isomer is prepared from benzenesulfonyl fluoride. The para- and meta-substituted boronic acids undergo efficient Sukuki-Miyaura coupling reactions with a range of aryl halides. We also report an efficient Rh(I)-catalyzed conjugate addition reaction using the para-substituted boronic acid.

  我们报告了邻，间和对磺酰氟取代的苯硼酸的高效和实用合成。对-和间-异构体的合成从适当的溴取代的苯磺酰氯开始，而邻位异构体由苯磺酰氟制备。对位和间位取代的硼酸会与一系列芳基卤化物进行有效的Sukuki-Miyaura偶联反应。我们还报道了使用对位取代的硼酸的有效的Rh（I）催化的共轭加成反应。
• 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。