3,3-二乙氧基-1-丙基硼酸频哪醇醚 | 165904-27-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 3,3-二乙氧基-1-丙基硼酸频哪醇醚
• 中文别名: 3,3-二乙氧基-1-丙硼酸频那醇酯
• 英文名称: 2-(3,3-diethoxypropyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 3,3-Diethoxy-1-propylboronic acid pinacol ester
• CAS: 165904-27-8
• 化学式: C₁₃H₂₇BO₄
• mdl: MFCD03788723
• 分子量: 258.166
• InChiKey: VEDSPUPKZZMMLL-UHFFFAOYSA-N

物化性质

• 稳定性/保质期：

  避免高温、火焰和强光。

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 安全说明：
  S24/25
• 储存条件：
  保存方法：密闭存放于阴凉、通风干燥处。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,3-Diethoxy-1-propylboronic 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: 3,3-Diethoxy-1-propylboronic acid pinacol ester
CAS number: 165904-27-8

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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, under −20◦C.
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: C13H27BO4
Molecular weight: 258.2

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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：

  3,3-二乙氧基-1-丙基硼酸频哪醇醚 在 2,4,5,6-四(9H-咔唑-9-基)异酞腈 作用下， 以 四氢呋喃 、 二丁醚 、 二甲基亚砜 为溶剂， 反应 21.17h， 生成 methyl 1-(4,4-diethoxybutyl)cyclobutane-1-carboxylate
  参考文献：
  名称：

  脱硼自由基加成-极性环化级联光氧化还原催化环丁烷合成

  摘要：

  描述了烷基硼酸酯的光氧化还原催化的甲基环丁烷化。该反应通过单电子转移诱导的脱硼自由基加成到缺电子烯烃上，然后进行单电子还原和极性 4- exo - tet环化与侧烷基卤化物。该方法成功的关键是使用易于氧化的芳基硼酸配合物。结构多样的环丁烷可以方便地由容易获得的烷基硼酸酯和一系列卤代烷基烯烃制备。温和的反应表现出优异的官能团耐受性，自由基加成-极性环化级联也能够合成3-、5-、6-和7-元环。

  DOI：

  10.1002/anie.201813917
• 作为产物：
  描述：

  丙烯醛缩二乙醇 在 Hg 作用下， 以63% (3.26 g, 12.63 mmol)的产率得到3,3-二乙氧基-1-丙基硼酸频哪醇醚
  参考文献：
  名称：

  Process for preparing bisallylboranes and nonaromatic boronic acids

  摘要：

  通过在惰性溶剂中将二烯与硼氢化钠在氧化剂1的存在下反应，制备公式（I）的双烯基硼烷的方法，其中原位生成的硼烷选择性地与二烯反应，形成公式（I）的双(烯基)硼烷，取代基R1至R6具有以下含义：R1-R6为H、芳基或取代或未取代的C1-C4烷基，或两个基团R可以闭合形成环状系统。作为氧化剂，可以使用例如烷基卤化物或二烷基硫酸酯。在一个特别优选的实施例中，所使用的二烯是2,5-二甲基己-2,4-二烯（R1、R2、R5、R6=methyl，R3、R4=H）。

  公开号：

  US20030096995A1

文献信息

• Enantioselective catalytic 1,2-boronate rearrangements
  作者：Hayden A. Sharma、Jake Z. Essman、Eric N. Jacobsen

  DOI：10.1126/science.abm0386

  日期：2021.11.5

  the construction of a wide variety of trisubstituted stereocenters through a catalytically accessed common chiral intermediate could prove highly enabling for the field of synthetic chemistry. We report the discovery of enantioselective, catalytic 1,2-boronate rearrangements for the synthesis of α-chloro pinacol boronic esters from readily available boronic esters and dichloromethane. The chiral building

  一种通过催化获得的常见手性中间体促进构建多种三取代立体中心的策略可以证明对合成化学领域具有高度的促进作用。我们报告了对映选择性、催化 1,2-硼酸酯重排的发现，用于从容易获得的硼酸酯和二氯甲烷合成 α-氯频哪醇硼酸酯。在这些反应中产生的手性结构单元可以经历两个连续的立体定向加工，以产生各种各样的三取代立体中心。对映选择性反应由锂-异硫脲-硼酸盐络合物催化，该络合物被提议通过由催化剂支架上的路易斯碱性官能团协调的双锂诱导氯化物提取来促进重排。
• Di(isopropylprenyl)borane: A New Hydroboration Reagent for the Synthesis of Alkyl and Alkenyl Boronic Acids
  作者：Alexey V. Kalinin、Stefan Scherer、Victor Snieckus

  DOI：10.1002/anie.200351312

  日期：2003.7.28