3,4,5-三甲氧基苯硼酸频那醇酯 | 214360-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3,4,5-三甲氧基苯硼酸频那醇酯
• 英文名称: 4,4,5,5-tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolane
• 英文别名: 3,4,5-trimethoxyphenylboronic acid pinacol ester；2-(3,4,5-trimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 214360-67-5
• 化学式: C₁₅H₂₃BO₅
• 分子量: 294.156
• InChiKey: SEARINNLCHQTJH-UHFFFAOYSA-N

物化性质

• 熔点：
  100-101.5 °C
• 沸点：
  385.6±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3,4,5-Trimethoxyphenylboronic acid, pinacol ester
Synonyms: 4,4,5,5-Tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolane

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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: 3,4,5-Trimethoxyphenylboronic acid, pinacol ester
CAS number: 214360-67-5

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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, refrigerated.
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: C15H23BO5
Molecular weight: 294.2

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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：

  3,4,5-三甲氧基苯硼酸频那醇酯 在 吡啶 、 potassium [¹⁸F]fluoride 、 potassium trifluoromethansulfonate 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 1-[¹⁸F]fluoro-3,4,5-trimethoxybenzene
  参考文献：
  名称：

  Synthesis of [¹⁸F]Arenes via the Copper-Mediated [¹⁸F]Fluorination of Boronic Acids

  摘要：

  A copper-mediated radiofluorination of aryl- and vinylboronic acids with (KF)-F-18 is described. This method exhibits high functional group tolerance and is effective for the radiofluorination of a range of electron-deficient, -neutral, and -rich aryl-, heteroaryl-, and vinylboronic acids. This method has been applied to the synthesis of [F-18]FPEB, a PET radiotracer for quantifying metabotropic glutamate 5 receptors.

  DOI：

  10.1021/acs.orglett.5b02875
• 作为产物：
  描述：

  1-溴-3,4,5-三甲氧基苯 在 盐酸 、 [1,3-双(二苯基膦基)丙烷]二氯化钯(II) 、 二异丙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 21.0h， 生成 3,4,5-三甲氧基苯硼酸频那醇酯
  参考文献：
  名称：

  胺-硼烷配合物：空气和水分稳定的伙伴，用于钯催化芳基溴化物和氯化物的硼化反应

  摘要：

  已经开发了一种直接在钯催化的硼化反应中使用胺-硼烷配合物的方法。该反应通过依次形成硼物质然后进行去质子化而产生氨基硼烷而进行。然后，该试剂可直接用于硼化过程中，经过处理后可生成各种硼酸衍生物。将反应物应用于（杂）芳基三氟甲磺酸酯，碘化物，溴化物和氯化物。

  DOI：

  10.1002/adsc.201401153

文献信息

• Regioselective Conversion of Arenes to<i>N</i>-aryl-1,2,3-triazoles Using CH Borylation
  作者：Rajavel Srinivasan、Anthony G. Coyne、Chris Abell

  DOI：10.1002/chem.201403021

  日期：2014.9.8

  A one‐pot protocol for the synthesis of N‐aryl 1,2,3‐triazoles from arenes by an iridium‐catalyzed CH borylation/copper catalyzed azidation/click sequence is described. 1 mol % of Cu(OTf)2 was found to efficiently catalyze both the azidation and the click reaction. The applicability of this method is demonstrated by the late‐stage chemoselective installation of 1,2,3‐triazole moiety into unactivated

  的单釜协议用于合成Ñ -芳基的1,2,3-三唑从芳烃通过铱催化的Ç  ħ硼化/铜催化的叠氮化/击序列进行说明。发现1mol％的Cu（OTf）2有效地催化了叠氮化和点击反应。1,2,3-三唑部分在化学上重要的未活化分子的后期化学选择性安装证明了该方法的适用性。
• Synthesis and biological evaluation of cis-restrained carbocyclic combretastatin A-4 analogs: Influence of the ring size and saturation on cytotoxic properties
  作者：Christina Nowikow、Rita Fuerst、Maria Kauderer、Christian Dank、Walther Schmid、Marian Hajduch、Jiri Rehulka、Sona Gurska、Olena Mokshyna、Pavel Polishchuk、István Zupkó、Petr Dzubak、Uwe Rinner

  DOI：10.1016/j.bmc.2019.07.048

  日期：2019.10

  physiological conditions, reducing the overall activity of the drug candidates. Herein, we report the preparation of cis-restrained carbocyclic analogs of CA-4. The compounds, which differ by the size and hybridization of the carbocyclic ring have been evaluated for their cytotoxic properties and their ability to inhibit tubulin polymerization. Biological data, supported by molecular docking studies, identified

  Combretastatin A-4（CA-4）是一种高度细胞毒性的天然产物，已经制备了几种衍生物，并已进行了临床试验。这些研究表明，天然产物的顺式-lb部分在生理条件下易于进行顺式/反式异构化，从而降低了候选药物的总体活性。在这里，我们报告顺式的制备约束的CA-4碳环类似物。已经评估了因碳环的大小和杂交而异的化合物的细胞毒性和抑制微管蛋白聚合的能力。在分子对接研究的支持下，生物学数据确定了天然产物的环丁烯基和环丁基衍生物是高度有前途的候选药物。
• Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C–H Borylation/N–C(O) Activation
  作者：Pengcheng Gao、Michal Szostak

  DOI：10.1021/acs.orglett.0c02105

  日期：2020.8.7

  Herein, we demonstrate that amides can be readily coupled with nonactivated arenes via sequential Ir-catalyzed C–H borylation/N–C(O) activation. This methodology provides facile access to biaryl ketones and biaryls by the sterically controlled Ir-catalyzed C–H borylation and divergent acyl and decarbonylative amide N–C(O) and C–C activation. The methodology diverts the traditional acylation and arylation

  在这里，我们证明酰胺可以通过连续的Ir催化的C–H硼酸酯化/ N–C（O）活化而容易地与未活化的芳烃偶联。这种方法可通过空间控制的Ir催化的C–H硼化以及不同的酰基和脱羰基酰胺N–C（O）和C–C活化来轻松获得联芳基酮和联芳基。该方法转移了传统的酰化和芳基化区域选择性，使我们能够直接利用容易获得的芳烃和酰胺来产生有价值的酮和联芳基。
• Rapid synthesis of bis(hetero)aryls by one-pot Masuda borylation–Suzuki coupling sequence and its application to concise total syntheses of meridianins A and G
  作者：Eugen Merkul、Elisabeth Schäfer、Thomas J. J. Müller

  DOI：10.1039/c1ob05310h

  日期：——

  3-(Hetero)aryl substituted indoles, 7-azaindoles, and pyrroles can be obtained in a very concise fashion via a one-pot Masuda borylation–Suzuki coupling sequence. The concise total syntheses of the marine natural products meridianins A (5) and G (4i) nicely illustrate the utility of this methodology.

  通过一锅增田（Masuda）硼酸酯化-铃木（Suzuki）偶联序列可以非常简明的方式获得3-（杂）芳基取代的吲哚，7-氮杂吲哚和吡咯。海洋天然产物子午线素A（5）和G（4i）的简洁的总合成很好地说明了该方法的实用性。
• Iron‐Catalyzed Fluoroalkylation of Arylborates with Sulfone Reagents: Beyond the Limitation of Reduction Potential
  作者：Zhiqiang Wei、Wenjun Miao、Chuanfa Ni、Jinbo Hu

  DOI：10.1002/anie.202102597

  日期：2021.6.7

  alkyl–aryl coupling reaction between sulfones and arylboron compounds has remained a challenge. We report the first iron-catalyzed radical difluoroalkylation of arylborates with N-heteroaryl sulfones. The coordination between the iron catalyst and the nitrogen atom of N-heteroaryl sulfones was identified to be important in overcoming the reduction potential limitation of sulfones in the intermolecular single-electron-transfer

  砜和芳基硼化合物之间的铁催化烷基-芳基偶联反应仍然是一个挑战。我们报告了第一个铁催化的芳基硼酸酯与 N-杂芳基砜的自由基二氟烷基化。铁催化剂与 N-杂芳基砜的氮原子之间的配位被认为对于克服分子间单电子转移过程中砜的还原电位限制很重要，这使得氟烷基 N-杂芳基砜（具有相对较高的还原电位）和非氟化烷基 N-杂芳基砜（具有低还原电位）作为强大的烷基化试剂。