4-甲氧甲酰苯硼酸频哪醇酯 | 171364-80-0

• 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 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲氧甲酰苯硼酸频哪醇酯
• 中文别名: 4-(甲氧羰基)苯硼酸频哪酯；对甲氧羰基苯硼酸频哪醇酯；4-(4,4,5,5-四甲基-1,3,2-二氧杂戊硼烷-2-基)苯甲酸甲酯；4-甲氧羰基苯硼酸频哪醇酯；4-甲酯基苯硼酸频呐醇酯
• 英文名称: methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• 英文别名: 4-methoxycarbonylphenylboronic acid pinacol ester；4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester；4-carbomethoxyphenylboronic acid pinacol ester；4-methoxyformylphenylboronic acid pinacol ester；para-methoxycarbonylphenylboronic acid pinacol ester；methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl) benzoate；4-(methoxycarbonyl)benzeneboronic acid pinacol ester
• CAS: 171364-80-0
• 化学式: C₁₄H₁₉BO₄
• mdl: MFCD02179438
• 分子量: 262.113
• InChiKey: REIZEQZILPXYKS-UHFFFAOYSA-N

物化性质

• 熔点：
  77-81 °C(lit.)
• 沸点：
  355.6±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  在常温常压下保持稳定，应避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 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

• TSCA：
  No
• 危险品标志：
  Xi
• 安全说明：
  S26,S37
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  常温下应密闭保存，在阴凉、通风和干燥的地方存放。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Methoxycarbonylphenylboronic acid, pinacol ester
Synonyms: Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

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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-Methoxycarbonylphenylboronic acid, pinacol ester
CAS number: 171364-80-0

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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：

  4-甲氧甲酰苯硼酸频哪醇酯 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 cesium fluoride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 生成 二甲基三联苯二羧酸
  参考文献：
  名称：

  Effect of the functionalisation route on a Zr-MOF with an Ir–NHC complex for catalysis

  摘要：

  一种新的铱N-杂环卡宾（NHC）金属连接物已经合成并首次引入到金属-有机框架（MOF）中，通过两种不同的途径实现：直接合成和后合成交换（PSE）。

  DOI：

  10.1039/c5cc03934g
• 作为产物：
  描述：

  4-丁酰基苯甲酸甲酯 在 吡啶 、 盐酸羟胺 、 sodium acetate 、 potassium carbonate 、 2-(4,5-二氢-4,4-二甲基-2-恶唑基)吡啶 、 四(3,5-二(三氟甲基)苯基)硼酸钠 、 三[3,4-双(三氟甲基)苯基]膦 、 palladium dichloride 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 4-甲氧甲酰苯硼酸频哪醇酯
  参考文献：
  名称：

  通过配体促进的CC键活化来转化芳基酮。

  摘要：

  芳族亲电试剂（芳基卤化物，芳基醚，芳基酸，芳基腈等）与亲核试剂的偶联是合成芳基化合物的核心方法。由于芳基酮的丰度，通过碳-碳键活化以类似方式进行芳基酮的转化可大大扩展合成芳基化合物的工具箱。这种方法的探索性研究通常基于环应变释放和螯合辅助引发的碳-碳裂解，并且产物也仅限于特定的结构基序。在这里，我们报告了一种配体促进β-碳消除的策略，以激活碳-碳键，这导致芳基酮发生一系列转化，从而生成有用的芳基硼酸酯，以及联芳基，芳基腈和芳基烯烃。吡啶-恶唑啉配体的使用对于这种催化转化至关重要。据报道，通过简单的一锅操作，芳基酮的克级硼酸酯化反应。该策略的潜在效用还通过丙磺舒，阿达帕林和脱氧雌酮，芬芳类香囊素和载脂蛋白的天然产物的晚期药物分子多样化而得到证明。

  DOI：

  10.1002/anie.202006740
• 作为试剂：
  描述：

  4-甲氧甲酰苯硼酸频哪醇酯 、 4-[3-iodo-1-[(1S)-1-(2-pyridyl)ethyl]pyrrolo[3,2-b]pyridin-6-yl]-3,5-dimethyl-isoxazole 在 4-甲氧甲酰苯硼酸频哪醇酯 作用下， 以72.7的产率得到methyl 4-[6-(3,5-dimethylisoxazol-4-yl)-1-[(1S)-1-(2-pyridyl)ethyl]pyrrolo[3,2-b]pyridin-3-yl]benzoate
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS AND USES THEREOF
  [FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS UTILISATIONS

  摘要：

  公式（I）的杂环化合物，其制备方法，含有该化合物的药物组合物以及它们的治疗用途。

  公开号：

  WO2014145051A1

文献信息

• Reductive arene ortho-silanolization of aromatic esters with hydridosilyl acetals
  作者：Yuanda Hua、Parham Asgari、Udaya Sree Dakarapu、Junha Jeon

  DOI：10.1039/c4cc09850a

  日期：——

  The design and application of a single-pot, reductive arene C–H bond silanolization of esters for synthesis of ortho-formyl arylsilanols.

  一锅法还原芳烃C-H键硅醇化酯的设计与应用，用于合成邻甲酰基芳基硅醇。
• 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。
• 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...
• Chan–Evans–Lam Amination of Boronic Acid Pinacol (BPin) Esters: Overcoming the Aryl Amine Problem
  作者：Julien C. Vantourout、Robert P. Law、Albert Isidro-Llobet、Stephen J. Atkinson、Allan J. B. Watson

  DOI：10.1021/acs.joc.6b00466

  日期：2016.5.6

  The Chan–Evans–Lam reaction is a valuable C–N bond forming process. However, aryl boronic acid pinacol (BPin) ester reagents can be difficult coupling partners that often deliver low yields, in particular in reactions with aryl amines. Herein, we report effective reaction conditions for the Chan–Evans–Lam amination of aryl BPin with alkyl and aryl amines. A mixed MeCN/EtOH solvent system was found

  Chan–Evans–Lam反应是有价值的C–N键形成过程。但是，芳基硼酸频哪醇（BPin）酯试剂可能很难成为偶合剂，常常导致收率低，特别是在与芳基胺反应时。在此，我们报告了烷基-芳基胺与芳基BPin的Chan-Evans-Lam胺化反应的有效反应条件。发现混合的MeCN / EtOH溶剂系统可以使用芳基胺形成有效的C–N键，而烷基胺的偶联则不需要EtOH。