2-乙酰氧基苯硼酸频那醇酯 | 480424-68-8

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 2-乙酰氧基苯硼酸频那醇酯
• 中文别名: 2-乙酰基氨基苯硼酸频哪醇酯；2-乙酰氧基苯硼酸频哪醇酯；醋酸-2-(4,4,5,5-四甲基-1,3,2-二氧杂硼烷-2-基)苯酯
• 英文名称: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate
• 英文别名: [2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] acetate
• CAS: 480424-68-8
• 化学式: C₁₄H₁₉BO₄
• mdl: MFCD03453062
• 分子量: 262.113
• InChiKey: KFBOKXXUJHAZIH-UHFFFAOYSA-N

物化性质

• 熔点：
  47-51 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  按规定使用和贮存不会分解，避免接触氧化物和水分。

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  N
• 安全说明：
  S61
• 危险类别码：
  R51/53,R40
• WGK Germany：
  3
• 危险品运输编号：
  UN 3077 9/PG 3
• 海关编码：
  2934999090
• 危险性防范说明：
  P210,P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P332+P313,P337+P313,P362,P370+P378,P403+P233,P403+P235,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  应将其存放在干燥、阴凉、密闭且惰性气体保护的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Acetoxyphenylboronic 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-Acetoxyphenylboronic acid, pinacol ester
CAS number: 480424-68-8

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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: C14H19BO4
Molecular weight: 262.1

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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.

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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-乙酰氧基苯硼酸频那醇酯 、 单氧化(~11~C)碳 在 四丁基氢氧化铵 、 palladium diacetate 、 三苯基膦 、 对苯醌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以15%的产率得到[(11)C]-aspirin
  参考文献：
  名称：

  的Pd（0）介导的[ 11 C]与[芳基和杂芳基硼酸频哪醇酯的羰基化11 C]在环境条件下一氧化碳和用于转化的简便方法[羰基- 11 C]酯[羰基- 11 C ^ ]酰胺

  摘要：

  已开发出一种新方法，用于在对苯醌和三苯膦在N，N的混合物中，用[ 11 C]一氧化碳进行Pd（0）介导的芳基/杂芳基硼酸频哪醇酯的[ 11 C]羰基化-二甲基甲酰胺（DMF）和甲醇（MeOH）或仅在环境温度和65°C下的MeOH。使用该方法，以各种不同的芳基/杂芳基硼酸酯的转化为相应的[羰基- 11 C]酯具有在6-80％的范围内衰变校正的放射化学产率。此外，一些[中羰基- 11C]酯用氢氧化钠或铵水溶液处理，得到对应的[羰基- 11 C]羧酸和酰胺，分别。该新方法还用于在水或DMF中使用甲醇或氢氧化四甲铵代替MeOH来直接合成[ 11 C]阿司匹林。

  DOI：

  10.1016/j.tet.2015.01.008
• 作为产物：
  描述：

  苯酚 在 5-甲基-2-(噻吩-3-基)吡啶 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 cobalt(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 24.11h， 生成 2-乙酰氧基苯硼酸频那醇酯
  参考文献：
  名称：

  用于定向 C(sp2)–H 和 C(sp3)–H 硼酸化不同类型底物的显着高效铱催化剂

  摘要：

  在这里，我们描述了一类新的 C-H 硼化催化剂的发现及其在芳族、杂芳族和脂肪族系统的区域选择性 C-H 硼化中的应用。新催化剂具有 Ir-C(噻吩基) 或 Ir-C(呋喃基) 阴离子配体，而不是标准 C-H 硼化条件中使用的二胺型中性螯合配体。据报道，这些新发现的催化剂的使用对不同种类的芳烃底物显示出优异的反应性和邻位选择性，并具有高分离产率。此外，该催化剂被证明对大量脂肪族底物的选择性 C(sp 3)–H 键硼化。杂环分子利用 C-H 键固有的高反应性选择性地硼化。已经使用相同的催化剂描述了许多后期 C-H 功能化。此外，我们表明其中一种催化剂甚至可以在露天用于 C(sp 2 )-H 和 C(sp 3 )-H 硼酸化，从而使该方法更加通用。初步的机理研究表明，活性催化中间体是 Ir(bis)boryl 络合物，连接的配体作为双齿配体。总的来说，这项研究强调了新型 C-H 硼酸化催化剂的发现，这些催化剂应该在

  DOI：

  10.1021/jacs.0c13415

文献信息

• Mechanism and Scope of Nickel-Catalyzed Decarbonylative Borylation of Carboxylic Acid Fluorides
  作者：Christian A. Malapit、James R. Bour、Simon R. Laursen、Melanie S. Sanford

  DOI：10.1021/jacs.9b08961

  日期：2019.10.30

  Article describes the development of a base-free, nickel-catalyzed decarbonylative coupling of carboxylic acid fluorides with diboron reagents to selectively afford aryl boronate ester products. Detailed studies were conducted to assess the relative rates of direct transmetalation between aryl boronate esters and diboron reagents and a bisphosphine nickel(aryl)(fluoride) intermediate. These investigations

  本文描述了无碱、镍催化的羧酸氟化物与二硼试剂的脱羰偶联的开发，以选择性地提供芳基硼酸酯产品。进行了详细研究以评估芳基硼酸酯和二硼试剂与双膦镍（芳基）（氟化物）中间体之间直接金属转移的相对速率。这些研究表明，二硼试剂与这种 Ni（芳基）（氟化物）中间体发生金属转移的速度明显快于它们的芳基硼酸酯同类物。此外，两种硼试剂对金属转移的反应性随着硼中心亲电性的增加而增强。这些机理见解被用来开发酰基氟的催化脱羰硼酰化，证明适用于各种（杂）芳基羧酸氟以及各种二硼试剂。酰基氟可直接由羧酸原位生成。此外，机理研究指导了这种转变的各种空气稳定镍预催化剂的鉴定。
• Catalyst‐Free Enantiospecific Olefination with In Situ Generated Organocerium Species
  作者：Arif Music、Clément Hoarau、Nicolas Hilgert、Florian Zischka、Dorian Didier

  DOI：10.1002/anie.201810327

  日期：2019.1.21

  triorganocerium reagents and their application in catalyst‐free Zweifel olefinations. These unique cerium species were generated through novel exchange reactions of organohalides with n‐Bu3Ce reagents. The adequate electronegativity of cerium allowed for compensating the disadvantages of both usually functional‐group‐sensitive organolithium species and less reactive organomagnesium reagents. Exchange reactions

  描述了三有机铈试剂的原位形成及其在无催化剂的Zweifel烯烃中的应用。这些独特的铈物种是通过有机卤化物与n- Bu 3 Ce试剂的新型交换反应生成的。铈具有足够的负电性，可以弥补通常对官能团敏感的有机锂物质和反应性较低的有机镁试剂的缺点。在芳基和烯基溴上进行交换反应，从而实现手性硼频哪醇酯的对映体特异性转化。最终，这些新的有机铈物种参与了可选择性和空间受阻的酮的选择性1,2-加成反应。
• PYRROLOTRIAZINES AS ALK AND JAK2 INHIBITORS
  申请人：Breslin Henry J.

  公开号：US20120028919A1

  公开（公告）日：2012-02-02

  The present invention provides a compound of formula I or a salt form thereof, wherein Q 1 , Q 2 , Q 3 , and Q 4 are as defined herein. The compound of formula I has ALK and/or JAK2 inhibitory activity, and may be used to treat proliferative disorders.

  本发明提供了公式I或其盐形式的化合物，其中Q1、Q2、Q3和Q4的定义如本文所述。公式I的化合物具有ALK和/或JAK2抑制活性，可用于治疗增生性疾病。
• Pyrrolotriazines as ALK and JAK2 inhibitors
  申请人：Breslin Henry J.

  公开号：US08471005B2

  公开（公告）日：2013-06-25

  The present invention provides a compound of formula I or a salt form thereof, wherein Q1, Q2, Q3, and Q4 are as defined herein. The compound of formula I has ALK and/or JAK2 inhibitory activity, and may be used to treat proliferative disorders.

  本发明提供了公式I或其盐形式的化合物，其中Q1、Q2、Q3和Q4的定义如本文所述。公式I的化合物具有ALK和/或JAK2抑制活性，并可用于治疗增殖性疾病。
• N,B-Bidentate Boryl Ligand-Supported Iridium Catalyst for Efficient Functional-Group-Directed C–H Borylation
  作者：Guanghui Wang、Li Liu、Hong Wang、You-Song Ding、Jing Zhou、Shuai Mao、Pengfei Li

  DOI：10.1021/jacs.6b11867

  日期：2017.1.11

  Convenient silylborane precursors for introducing N,B-bidentate boryl ligands onto transition metals were designed, prepared, and employed in ready formation of irdium(III) complexes via Si-B oxidative addition. A practical, efficient catalytic ortho-borylation reaction of arenes with a broad range of directing groups was developed using an in situ generated catalyst from the silylborane preligand 3c and [IrCl(COD)](2).