4-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯甲酸乙酯 | 195062-62-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯甲酸乙酯
• 中文别名: 4-乙氧羰基苯硼酸频哪醇酯
• 英文名称: ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• 英文别名: 4-ethoxycarbonylphenylboronic acid pinacol ester；4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid ethyl ester；4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)benzoic acid ethyl ester
• CAS: 195062-62-5
• 化学式: C₁₅H₂₁BO₄
• mdl: MFCD03453659
• 分子量: 276.14
• InChiKey: NCVIYKCFTYSAGN-UHFFFAOYSA-N

物化性质

• 沸点：
  330 °C(lit.)
• 密度：
  1.052 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  避氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.533
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  保存方法：在4°C以下的环境中密闭保存。

SDS

Name:	Ethyl 4-(4 4 5 5-tetramethyl-1 3 2-dioxaborolan-2-yl)benzoate Material Safety Data Sheet
Synonym:
CAS:	195062-62-5

Section 1 - Chemical Product MSDS Name:Ethyl 4-(4 4 5 5-tetramethyl-1 3 2-dioxaborolan-2-yl)benzoate Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
195062-62-5	Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dio		unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Keep refrigerated. (Store below 4C/39F.) Store in a tightly closed container. Store in a dry area.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 195062-62-5: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Viscous liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 330 deg C @760mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density: 1.052
Molecular Formula: C15H21BO4
Molecular Weight: 276.14

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, boron oxides.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 195062-62-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 195062-62-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 195062-62-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 195062-62-5 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯甲酸乙酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 4,4'-二羟甲基联苯
  参考文献：
  名称：

  Synthesis and characterization of novel unnatural bichalcones

  摘要：

  联苯-4,4′-二甲醛（4）和 4,4′-二氧苯甲醛（8）与各自的苯乙酮类似物通过克莱森-施密特缩合反应制备出了五种双卡酮（5-1 ∼ 5-4，9），然后通过 1H-NMR、13C-NMR 和质量分析进行了全面鉴定。

  DOI：

  10.1007/s12272-010-1205-2
• 作为产物：
  描述：

  4-乙酰基苯甲酸乙酯 在 吡啶 、 2,6-二叔丁基-4-甲基苯酚 、 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-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)苯甲酸乙酯
  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

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。
• 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...
• Starburst Triarylamine Donor-Based Metal-Free Photosensitizers for Photocatalytic Hydrogen Production from Water
  作者：Po-Yu Ho、Yi Wang、Sze-Chun Yiu、Wai-Hong Yu、Cheuk-Lam Ho、Shuping Huang

  DOI：10.1021/acs.orglett.7b00042

  日期：2017.3.3

  Three metal-free molecular photosensitizers (S1–S3) featuring a starburst triarylamine donor moiety have been synthesized. They show attractive photocatalytic performance in visible light-driven H2 production from water in their platinized TiO2 composites. A remarkable H2 turnover number (TON) of 10 200 (48 h) was achieved in an S1-anchored system.

  合成了三种具有星爆三芳基胺供体部分的无金属分子光敏剂（S1 - S3）。它们在其镀铂的TiO 2复合材料中由水产生的可见光驱动的H 2中显示出有吸引力的光催化性能。在S1锚固系统中，H 2转换数（TON）达到了10200 （48小时）。
• Stereoselective Synthesis of Highly Substituted Enamides by an Oxidative Heck Reaction
  作者：Yu Liu、Dan Li、Cheol-Min Park

  DOI：10.1002/anie.201101550

  日期：2011.8.1

  Functionalization of enamides under Heck conditions has been limited to those with unsubstituted vinyl groups. By tuning reaction parameters that allow for the balance between stability and reactivity of reactants, the oxidative Heck cross‐coupling to produce highly substituted enamides in good to excellent yields was achieved (see scheme).

  在Heck条件下，酰胺的功能仅限于具有未取代乙烯基的酰胺。通过调整反应参数以实现反应物的稳定性和反应性之间的平衡，可以实现氧化Heck交叉偶联，从而以良好或优异的收率生产高度取代的酰胺（参见方案）。