二对甲苯基硼酸 | 66117-64-4

• 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: 二对甲苯基硼酸
• 英文名称: di(p-tolyl)borinic acid
• 英文别名: bis(p-tolyl)borinic acid；bis(4-tolyl)borinic acid；bis(4-methylphenyl)borinic acid；hydroxydi-p-tolylborane；Hydroxydip-tolylborane
• CAS: 66117-64-4
• 化学式: C₁₄H₁₅BO
• 分子量: 210.084
• InChiKey: ZJHMSSYDWCPSFN-UHFFFAOYSA-N

物化性质

• 溶解度：
  soluble in No data available

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Hydroxydip-tolylborane
Synonyms: Bis(4-tolyl)boronic acid

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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: Hydroxydip-tolylborane
CAS number: 66117-64-4

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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.
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: C14H15BO
Molecular weight: 210.1

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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：

  二对甲苯基硼酸 在 水 、 溴 作用下， 生成 4-甲苯硼酸
  参考文献：
  名称：

  Mel'nikow, Zhurnal Obshchei Khimii, 1936, vol. 6, p. 636,638,639

  摘要：

  DOI：
• 作为产物：
  描述：

  对溴甲苯 在 magnesium 、 苯基溴化镁 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 二对甲苯基硼酸
  参考文献：
  名称：

  通过胺-硼烷配合物的直接芳基化反应生成的硼酸：空气和水稳定的硼源

  摘要：

  摘要 使用胺-硼烷配合物作为对水和空气不敏感的硼化剂，可以优化硼酸和硼酸酯的合成。该反应在适宜的条件下使用非低温温度进行，并且没有快速色谱，并且没有硼杂质。该反应通过串联脱氢-双重加成机理进行。 使用胺-硼烷配合物作为对水和空气不敏感的硼化剂，可以优化硼酸和硼酸酯的合成。该反应在适宜的条件下使用非低温温度进行，并且没有快速色谱，并且没有硼杂质。该反应通过串联脱氢-双重加成机理进行。

  DOI：

  10.1055/s-0036-1588345

文献信息

• Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis
  作者：Fengze Wang、Chen Wang、Guoping Sun、Gang Zou

  DOI：10.1016/j.tetlet.2019.151491

  日期：2020.2

  A highly efficient cross-coupling of cost-effective diarylborinic acids with both isolatable and latent arenediazoniums, i.e. tetrafluoroborates and aryltriazenes, respectively, has been developed with a practical palladium catalyst system under base-free conditions in open flask at room temperature. A variety of electronically and sterically various biaryls, in particular, those bearing a coordinative

  低成本的二芳基硼酸与可分离的和潜在的芳族重氮鎓（即四氟硼酸酯和芳基三氮烯）的高效交叉偶联已在实用的钯催化剂体系下，在无碱条件下于室温下在敞口烧瓶中开发出来。通过使用0.3mol％的乙酸钯作为催化剂，可以以良好或优异的产率获得多种电子和空间上不同的联芳基，特别是那些带有配位邻位取代基的联芳基。该方案的特征包括二芳基硼酸的成本效益，对杂原子邻位取代底物的功效以及对芳基氯化物的高化学选择性，已在杀菌剂Boscalid的实际合成中得到了明确证明。
• Base-assisted, copper-catalyzed N-arylation of (benz)imidazoles and amines with diarylborinic acids
  作者：Changwei Guan、Yuanyuan Feng、Gang Zou、Jie Tang

  DOI：10.1016/j.tet.2017.10.043

  日期：2017.12

  cost-effective aryl source has been efficiently effected via Cu(OAc)2-catalyzed Chan-Lam coupling in assistance of tetramethylethylenediamine (TMEDA) in methanol and pyridine (Py) in dichloromethane, respectively, in air at room temperature. The diarylborinic acids could be well accommodated by the Chan-Lam coupling oxidative conditions containing a proper combination of bases and solvents. The steric

  借助Cu（OAc）2催化的Chan-Lam偶联，借助四甲基乙二胺（TMEDA）在甲醇和吡啶（Py）中的催化作用，已有效地实现了（苯）咪唑和胺与二芳基硼酸作为具有成本效益的芳基源的N-芳基化作用。室温下分别置于二氯甲烷中。包含适当的碱和溶剂组合的Chan-Lam偶联氧化条件可以很好地容纳二芳基硼酸。与电子因素相比，使用高阶芳基硼试剂时，空间位阻似乎对铜催化的N-芳基化的影响更大，尤其是对于低反应性苯胺和脂肪族胺而言。
• Design, Synthesis and Evaluation of Oxazaborine Inhibitors of the NLRP3 Inflammasome
  作者：Alex G. Baldwin、Victor S. Tapia、Tessa Swanton、Claire S. White、James A. Beswick、David Brough、Sally Freeman

  DOI：10.1002/cmdc.201700731

  日期：2018.2.20

  gout, atherosclerosis, type II diabetes and Alzheimer's disease. In this study, we report the design, synthesis and biological evaluation of novel boron compounds (NBCs) as NLRP3 inflammasome inhibitors. Structure-activity relationships (SAR) show that 4-fluoro substituents on the phenyl rings retain NLRP3 inhibitory activity, whereas more steric and lipophilic substituents diminish activity. Loss of

  NLRP3炎症小体是无菌炎症反应的重要调节因子，其被宿主衍生的无菌分子激活导致胞内caspase-1的激活，促炎细胞因子白细胞介素-1β（IL-1β）/IL-的处理。 18、焦亡细胞死亡。NLRP3 的不当激活会引发慢性炎症反应，并与多种非传染性疾病有关，包括痛风、动脉粥样硬化、II 型糖尿病和阿尔茨海默病。在这项研究中，我们报告了作为 NLRP3 炎性体抑制剂的新型硼化合物 (NBC) 的设计、合成和生物学评价。结构-活性关系 (SAR) 显示苯环上的 4-氟取代基保留了 NLRP3 抑制活性，而更多的空间和亲脂性取代基会降低活性。如果恶唑硼啉环上的 CCl3 基团被 CF3 基团取代，也会观察到抑制活性的丧失。这些发现提供了对 NBC 系列的更多了解，并将有助于开发这些 NLRP3 抑制剂作为无菌炎症性疾病的工具化合物或治疗候选药物。
• Palladium-Catalyzed Cross-CouplingReaction of Potassium Diaryldifluoroborates with Aryl Halides
  作者：Takatoshi Ito、Toshiyuki Iwai、Takumi Mizuno、Yoshio Ishino

  DOI：10.1055/s-2003-40851

  日期：——

  The catalytic cross-coupling reaction of potassium di­aryldifluoroborates with aryl halides proceeds to afford the biphenyls in good yields. These salts on an arylation reagent were readily prepared via a protocol of the Grignard method and transformation to potassium salts. Two aryl groups of these salts were efficiently transferred in the Suzuki-Miyaura reaction.

  钾二芳基二氟硼酸盐与芳烃卤化物的催化交叉耦合反应能够以良好的产率产生产酚。通过格氏试剂法及转化为钾盐的步骤，这些盐作为芳烃化试剂被容易制备。通过铃木-宫浦反应，这些盐的两个芳基高效转移。
• Highly efficient synthesis of aryl ketones by PEPPSI-palladium catalyzed acylative Suzuki coupling of amides with diarylborinic acids
  作者：Chen Wang、Lingyun Huang、Fengze Wang、Gang Zou

  DOI：10.1016/j.tetlet.2018.05.003

  日期：2018.6

  An improved acylative cross-coupling of various N-methyl-N-tosyl amides with diarylborinic acids for synthesis of aryl ketones is developed. In most cases, aryl ketones could be obtained in excellent yields by using 1 mol% 2,6-diisopropylphenylimidazolylidene and 3-chloropyridine co-supported palladium chloride as catalyst in the presence of 3 equiv. K2CO3 as base in refluxing THF. The readily prepared

  已开发了用于合成芳基酮的各种N-甲基-N-甲苯磺酰基酰胺与二芳基硼酸的改进的酰基交叉偶联。在大多数情况下，在3当量的存在下，通过使用1mol％的2,6-二异丙基苯基咪唑基亚甲基和3-氯吡啶共负载的氯化钯作为催化剂，可以以优异的产率获得芳基酮。在回流的THF中，以K 2 CO 3为碱。容易制备且具有成本效益的底物，N-甲基-N-甲苯磺酰胺和二芳基硼酸，以及可商购的催化剂体系，保证了实用和有效地获得芳基酮。