4-三甲硅基苯硼酸频呐醇酯 | 1186026-67-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 4-三甲硅基苯硼酸频呐醇酯
• 中文别名: 4-三甲基甲硅烷基苯硼酸频那醇酯
• 英文名称: trimethyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane
• 英文别名: 4-trimethylsilylphenylboronic acid pinacol ester；trimethyl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane
• CAS: 1186026-67-4
• 化学式: C₁₅H₂₅BO₂Si
• 分子量: 276.259
• InChiKey: OPGOPAKVZDQUMR-UHFFFAOYSA-N

物化性质

• 沸点：
  335.4±25.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

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：
  存储条件：2-8℃，干燥且密封。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Trimethylsilylphenylboronic acid pinacol ester
Synonyms: 4,4,5,5-Tetramethyl-2-(4-trimethylsilanyl-phenyl)-[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: 4-Trimethylsilylphenylboronic acid pinacol ester
CAS number: 1186026-67-4

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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: C15H25BO2Si
Molecular weight: 276.3

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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, sulfur 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：

  4-三甲硅基苯硼酸频呐醇酯 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 、 邻四氯苯醌 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 10.0h， 以70%的产率得到4,4'-二(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)联苯
  参考文献：
  名称：

  Pd/邻氯苯醌催化芳基三甲基硅烷的氧化均偶联反应

  摘要：

  Pd/o-氯苯醌催化体系实现了芳基三甲基硅烷的实际氧化均偶联反应。该反应显示出对溴、氟、酯和甲氧基的良好官能团耐受性，得到一系列带有吸电子和供电子基团的联芳基。硼酸酯基团也保留在联芳基上，没有任何 Ar-B 键断裂，这对于正交耦合非常有利。

  DOI：

  10.1246/cl.170723
• 作为产物：
  描述：

  对-(三甲基甲硅烷)苯硫酚 在 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride 、 sodium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.5h， 生成 4-三甲硅基苯硼酸频呐醇酯
  参考文献：
  名称：

  钯催化本位芳基硫化物与Diborons的-Borylation

  摘要：

  一种催化宫浦型本位与二硼试剂芳基硫化物的-borylation已经实现，从而提供合成的使用arylboronate酯。将本来就不愿意的C–S键转换为C–B键的关键条件包括钯-NHC（N-杂环卡宾）预催化剂，双（频哪醇）二硼和六甲基二硅叠氮化锂。该协议适用于合理范围的芳基烷基硫化物。在二苯硫醚的反应中观察到双重硼化。

  DOI：

  10.1021/acs.orglett.6b01305

文献信息

• Selective Transformation of Strychnine and 1,2-Disubstituted Benzenes by C–H Borylation
  作者：Yutaro Saito、Kotono Yamanoue、Yasutomo Segawa、Kenichiro Itami

  DOI：10.1016/j.chempr.2020.02.004

  日期：2020.4

  as natural products, pharmaceuticals, and π-conjugated systems are at the heart of constructing and modifying organic molecules, whereby the selectivity and predictability are of the utmost importance. Herein, we report the highly C3-selective C–H borylation of strychnine along with olefin isomerization, catalyzed by an iridium complex with a diphosphine ligand. This method enabled us to rapidly produce

  复杂分子（例如天然产物，药物和π共轭体系）的C–H功能化是构建和修饰有机分子的核心，因此，选择性和可预测性至关重要。在本文中，我们报道了由铱与二膦配体的配合物催化的士的宁的高度C3选择性C–H硼氢化以及烯烃异构化。这种方法使我们能够通过使用相应的C3硼化和异构化的类似物作为常见的合成中间体，快速生产15种士的宁衍生物。目前的催化剂体系通常对不对称1,2-二取代苯衍生物的C–H官能化也有效，包括稠合的π-体系（黄嘌呤，芴，萘和蒽）和药物（硝苯地平），
• Identification and structure activity relationship of novel flavone derivatives that inhibit the production of nitric oxide and PGE 2 in LPS-induced RAW 264.7 cells
  作者：Ji-Young An、Hwi-Ho Lee、Ji-Sun Shin、Hyung-Seok Yoo、Jong Seon Park、Seung Hwan Son、Sang Won Kim、Jihyun Yu、Jun Lee、Kyung-Tae Lee、Nam-Jung Kim

  DOI：10.1016/j.bmcl.2017.03.057

  日期：2017.6

  In an effort to identify novel anti-inflammatory compounds, a series of flavone derivatives were synthesized and biologically evaluated for their inhibitory effects on the production of nitric oxide (NO) and prostaglandin E2 (PGE2), representative pro-inflammatory mediators, in LPS-induced RAW 264.7 cells. Their structure-activity relationship was also investigated. In particular, we found that compound

  为了鉴定新型抗炎化合物，合成了一系列黄酮衍生物，并对其在LPS-中对代表性的促炎性介质一氧化氮（NO）和前列腺素E2（PGE2）产生的抑制作用进行了生物学评估。诱导的RAW 264.7细胞。还研究了它们的构效关系。尤其是，我们发现与木犀草素（一种被称为强效抗炎剂的天然黄酮）相比，化合物3g对PGE2的产生显示出更强的抑制活性，对NO生成具有类似的抑制活性，并且细胞毒性也较弱。
• Direct Stereospecific Amination of Alkyl and Aryl Pinacol Boronates
  作者：Scott N. Mlynarski、Alexander S. Karns、James P. Morken

  DOI：10.1021/ja305448w

  日期：2012.10.10

  The direct amination of alkyl and aryl pinacol boronates is accomplished with lithiated methoxyamine. This reaction directly provides aliphatic and aromatic amines, stereospecifically, and without preactivation of the boronate substrate.

  烷基和芳基频哪醇硼酸酯的直接胺化是用锂化甲氧基胺完成的。该反应直接提供脂肪族和芳香族胺，立体定向，并且没有硼酸酯底物的预活化。
• Cross‐Coupling through Ag(I)/Ag(III) Redox Manifold
  作者：Luca Demonti、Nathalie Saffon‐Merceron、Nicolas Mézailles、Noel Nebra

  DOI：10.1002/chem.202102836

  日期：2021.11.5

  trifluoromethylation via AgI/AgIII redox shuttles are herein deciphered. This innovative cross-coupling, analogous to the CEL coupling popularized by copper, involves: i) easy AgI/AgIII 2e− oxidation; ii) phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) benzotrifluoride production from aryl-AgIII intermediates. Now, AgIIICF3 chemistry is safe and reachable from AgF, KF, CF3TMS and air.

  教银做伎俩。通过Ag I / Ag III氧化还原穿梭进行氧化三氟甲基化的最关键步骤在本文中被破译。这种创新的交叉耦合类似于铜普及的 CEL 耦合，包括：i)容易的 Ag I /Ag III 2 e -氧化；ii)苯连接到 Ag III 上；iii)硼到 Ag III芳基转移；和ⅳ）三氟甲苯产量从芳基的Ag III中间体。现在，Ag III CF 3化学是安全的，可以从 AgF、KF、CF 3 TMS 和空气中获得。
• Sodium silylsilanolate enables nickel-catalysed silylation of aryl chlorides
  作者：Kenshiro Hitoshio、Hiroki Yamagishi、Jun Shimokawa、Hideki Yorimitsu

  DOI：10.1039/d1cc02683f

  日期：——

  Structurally diverse aryl chlorides were silylated with sodium silylsilanolate reagents in the presence of a Ni(cod)2 catalyst complexed with a phosphine ligand; PMe2Ph for electron-rich substrates, and PCy2Ph for electron-deficient ones. The mild reaction conditions allowed the silylation of various aryl chlorides including functionalised drug molecules.

  在与膦配体络合的 Ni(cod) 2催化剂存在下，结构多样的芳基氯化物用甲硅烷基硅烷醇钠试剂甲硅烷基化；PMe 2 Ph 用于富电子底物，PCy 2 Ph 用于缺电子底物。温和的反应条件允许包括官能化药物分子在内的各种芳基氯化物进行硅烷化。

表征谱图