3-(N,O-二甲基羟基L甲酰氨)苯基硼酸 | 723281-57-0

• 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-(N,O-二甲基羟基L甲酰氨)苯基硼酸
• 中文别名: 3-(N,O-二甲基羟氨基羰基)苯硼酸；3-[甲氧基(甲基)氨甲酰基]苯硼酸
• 英文名称: 3-(N,O-dimethylhydroxylaminocarbonyl)phenylboronic acid
• 英文别名: 3-(N,O-dimethylhydroxylaminocarbonyl)benzeneboronic acid；(3-(methoxy(methyl)carbamoyl)phenyl)boronic acid；[3-[methoxy(methyl)carbamoyl]phenyl]boronic acid
• CAS: 723281-57-0
• 化学式: C₉H₁₂BNO₄
• mdl: MFCD04115699
• 分子量: 209.01
• InChiKey: IYZAWDLXZOCCSB-UHFFFAOYSA-N

物化性质

• 熔点：
  66-70°C
• 沸点：
  453.9±47.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S26,S36/37/39

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
3-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid
Product Name:
Synonyms: N-Methoxy-N-Methyl 3-boronobenzamide

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
3-(N,O-Dimethylhydroxylaminocarbonyl)phenylboronic acid
Ingredient name:
CAS number: 723281-57-0

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C9H12BNO4
Molecular weight: 209.0

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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, nitrogen oxides.

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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：

  3-(N,O-二甲基羟基L甲酰氨)苯基硼酸 在 1,10-菲罗啉 、 copper iodide - dimethyl sulfide complex 、 二叔丁基过氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 64.0h， 生成 3-(N,O-dimethylhydroxylaminocarbonyl)diphenylmethane
  参考文献：
  名称：

  药效团的原料：铜催化的廉价芳烃氧化芳基化，可直接获得二芳基烷烃

  摘要：

  已经确定了一种 Cu 催化的方法，用于苄基 CH 键与芳基硼酸酯的选择性氧化芳基化。所得的 1,1-二芳基烷烃可直接从含有伯和仲苄基 CH 键的廉价烷基芳烃（如甲苯或乙苯）中获得。所有催化剂组分均可以低成本商购获得，并且芳基硼酸酯可商购获得或容易从商购硼酸获得。强调了这些方法在药物化学应用中的潜在效用。

  DOI：

  10.1021/jacs.7b03387

文献信息

• Copper-Catalyzed Synthesis of Activated Sulfonate Esters from Boronic Acids, DABSO, and Pentafluorophenol
  作者：Vincent Vedovato、Eric P. A. Talbot、Michael C. Willis

  DOI：10.1021/acs.orglett.8b02445

  日期：2018.9.7

  The synthesis of pentafluorophenyl (PFP) sulfonate esters based on the Pd-catalyzed sulfination of aryl and heteroaryl boronic acids is reported. The sulfinate intermediates are converted in situ to the corresponding sulfonate esters using a copper-catalyzed oxidative process, providing a broad range of PFP esters in good yields.

  报道了基于Pd催化的芳基和杂芳基硼酸的硫化，合成五氟苯基（PFP）磺酸酯。使用铜催化的氧化过程将亚磺酸盐中间体原位转化为相应的磺酸酯，从而以良好的收率提供了多种PFP酯。
• Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids
  作者：Thomas J. A. Graham、Abigail G. Doyle

  DOI：10.1021/ol300364s

  日期：2012.3.16

  nes is described. Under base-free conditions, readily accessible 2-ethoxy-2H-chromenes undergo Csp3–O activation and Csp3–C bond formation in the presence of an inexpensive nickel catalyst and boronic acids. This new strategy enables broad access to 2-substituted-2H-chromenes and has been applied to the late-stage incorporation of complex molecules, including the pharmaceuticals loratidine and indomethacin

  描述了一种用于合成 2-芳基-和杂芳基-2 H-色烯的模块化和高效方案。在无碱条件下，容易获得的 2-乙氧基-2 H-色烯在廉价的镍催化剂和硼酸存在下经历 C sp 3 -O 活化和 C sp 3 -C 键形成。这种新策略可以广泛使用 2-取代-2 H-色烯，并已应用于复杂分子的后期掺入，包括药物氯雷他定和吲哚美辛甲酯。
• A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C–C Bond Scission
  作者：Neil J. McAlpine、Long Wang、Brad P. Carrow

  DOI：10.1021/jacs.8b10007

  日期：2018.10.24

  Substituted 1,3-dienes are valuable synthetic intermediates used in myriad catalytic transformations, yet modern catalytic methods for their preparation in a highly modular fashion using simple precursors are relatively few. We report here an aerobic boron Heck reaction with cyclobutene that forms exclusively linear 1-aryl-1,3-dienes using (hetero)arylboronic acids, or 1,3,5-trienes using alkenylboronic

  取代的 1,3-二烯是用于无数催化转化的有价值的合成中间体，但使用简单前体以高度模块化方式制备它们的现代催化方法相对较少。我们在此报告了与环丁烯的需氧硼 Heck 反应，该反应使用（杂）芳基硼酸形成专门的线性 1-芳基-1,3-二烯，或使用烯基硼酸形成 1,3,5-三烯，而不是典型的 Heck 产物（即取代的环丁烯）。实验和计算机理数据支持 CC 键断裂的周环机制，该机制使环烯烃能够规避 Heck 型反应中与二烯试剂相关的既定限制。