4-乙酰苯基硼酸,醇酯 | 171364-81-1

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙酰苯基硼酸,醇酯
• 中文别名: 4-乙酰苯硼酸频哪醇酯；1-[4-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-YL)苯基]乙酮
• 英文名称: 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone
• 英文别名: 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-one；4-acetylphenylboronic acid pinacol ester；2-(4-acetylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone
• CAS: 171364-81-1
• 化学式: C₁₄H₁₉BO₃
• mdl: MFCD05863922
• 分子量: 246.114
• InChiKey: BATKIZWNRQGSKE-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65°C
• 沸点：
  356.6±25.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 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
• 储存条件：
  存放在室温、干燥且密封的环境中。

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Acetylphenylboronic 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: 4-Acetylphenylboronic acid, pinacol ester
CAS number: 171364-81-1

---

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, refrigerated.
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: C14H19BO3
Molecular weight: 246.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide.

---

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：

  4-乙酰苯基硼酸,醇酯 在 air 作用下， 反应 16.0h， 以22.1 mg的产率得到对羟基苯乙酮
  参考文献：
  名称：

  芳基卤化物的可见光光氧化还原硼化和随后的好氧氧化羟化反应

  摘要：

  开发了有效和实用的芳基卤化物的可见光光氧化还原硼化和随后的好氧氧化羟基化反应。该方案使用容易获得的芳基卤化物和双（频哪醇）二硼烷为原料，fac- Ir（ppy）3作为光催化剂，并以高收率获得了相应的芳基硼酸酯和苯酚。该方法显示出一些优点，包括简单的设备，温和的条件，容易的操作和广泛的底物范围。因此，它们应该为化学转化提供有价值的策略。

  DOI：

  10.1021/acs.orglett.6b02553
• 作为产物：
  描述：

  4-乙酰基苯甲酰氯 在 4-二甲氨基吡啶 、 Wilkinson's catalyst 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 27.0h， 生成 4-乙酰苯基硼酸,醇酯
  参考文献：
  名称：

  Rh催化的酰胺酰胺的无碱脱羰基硼化反应

  摘要：

  我们报告了铑催化的酰胺的无碱脱羰基硼化。由芳基扭曲酰胺合成通用的芳基硼酸酯是通过脱羰铑（I）催化和高度选择性的N–C（O）插入来实现的。该方法在非常实用的无添加剂Rh（I）催化剂体系中非常引人注目。该方法显示出宽泛的官能团耐受性和出色的底物范围，包括通过不同的N-C / C-Br裂解和后期药物硼化进行的位点选择性脱羰基硼化/ Heck交叉偶联。

  DOI：

  10.1021/acs.joc.0c02157

文献信息

• 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 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...
• Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities
  作者：Bing Zhang、Xin Xu、Lei Tao、Zhenyang Lin、Wanxiang Zhao

  DOI：10.1021/acscatal.1c02685

  日期：2021.8.6

  available ketones. Mechanistic studies suggest that this Rh-catalyzed deoxygenative borylation of ketones goes through an alkene intermediate, which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates. The different steric effects of PPh2Me and P(nBu)3 were found to be responsible for product selectivity by density functional theory calculations. The alkene intermediate

  在这里，我们报告了一种有效的铑催化酮脱氧硼酸化合成烷基硼酸酯，其中区域选择性可以通过选择配体来切换。直链烷基硼酸酯仅在 P( n Bu) 3存在下获得，PPh 2 Me 有利于支链烷基硼酸酯的形成。该协议还允许从现成的酮中获取 1,1,2-三硼酸酯。机理研究表明，这种 Rh 催化的酮类脱氧硼酸化反应经过烯烃中间体，该中间体经历区域发散硼氢化反应，得到直链和支链烷基硼酸酯。PPh 2 Me 和 P( n Bu) 3的不同空间位阻效应通过密度泛函理论计算发现是产物选择性的原因。烯烃中间体也可以依次进行脱氢硼酸化和硼氢化反应以提供三硼酸酯。
• 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。
• Iridium-Catalyzed Arene <i>Ortho</i>-Silylation by Formal Hydroxyl-Directed C−H Activation
  作者：Eric M. Simmons、John F. Hartwig

  DOI：10.1021/ja1086547

  日期：2010.12.8

  the ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives has been developed in which a hydroxyl group formally serves as the directing element for Ir-catalyzed arene C-H bond activation. One-pot generation of a (hydrido)silyl ether from the carbonyl compound or alcohol is followed by dehydrogenative cyclization at 80-100 °C in the presence of norbornene as a hydrogen acceptor

  已开发出芳基酮、苯甲醛和苯甲醇衍生物的邻甲硅烷化策略，其中羟基正式作为 Ir 催化芳烃 CH 键活化的指导元素。从羰基化合物或醇一锅生成（氢化）甲硅烷基醚，然后在降冰片烯作为氢受体和 1 mol % [Ir(cod)OMe ]2 和 1,10-菲咯啉作为催化剂形成苯并恶唑。通过 Tamao-Fleming 氧化或 Hiyama 交叉偶联转化为苯酚或联芳基衍生物证明了苯并恶唑产品的合成效用。CH 甲硅烷基化产物的这两种转化都利用系统中的 Si-O 键，并通过用氢氧化物活化甲硅烷基部分来进行，