硼酸频哪醇酯 | 25240-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 溴苄基硼酸频哪醇酯
• 中文名称: 硼酸频哪醇酯
• 英文名称: pinacolboronic acid
• 英文别名: pinacolborane；HOBpin；2-Hydroxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 25240-59-9
• 化学式: C₆H₁₃BO₃
• mdl: MFCD15143603
• 分子量: 143.978
• InChiKey: ZZPNDIHOQDQVNU-UHFFFAOYSA-N

物化性质

• 沸点：
  141.8±23.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少量）、氯仿（少量）、甲醇（少量）

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335,H361
• 储存条件：
  存放条件：室温、密封、干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boric acid, pinacol ester
Synonyms: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol

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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: Boric acid, pinacol ester
CAS number: 25240-59-9

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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: C6H13BO3
Molecular weight: 144.0

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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：

  硼酸频哪醇酯 、 二甲基苯基硅烷 在 [Ru(p-cymene)Cl2(pyridine)] 、 水 作用下， 以 甲苯 为溶剂， 反应 26.0h， 以95%的产率得到dimethyl(phenyl)((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane
  参考文献：
  名称：

  钌催化的硼硅氧烷多组分合成

  摘要：

  我们提出了直接从一锅钌催化的硼烷，硅烷和水的多组分方法直接使用多组分方法经济地合成硼烷硅氧烷的方法

  DOI：

  10.1039/c7cc00787f
• 作为产物：
  描述：

  trimethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-methylbenzyl]-quaternaryammonium bromide 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 、 双氧水 作用下， 以 aq. phosphate buffer 、 乙醇 、 重水 、 二甲基亚砜 、 甲苯 、 乙腈 为溶剂， 反应 16.0h， 生成 硼酸频哪醇酯
  参考文献：
  名称：

  取代基对芳基硼酸酯前体的氧化甲基醌氧化生成的影响

  摘要：

  一系列含有不同芳族取代基和各种苄基离去基团（BR或N-芳基硼酸酯的+我3溴- ）已被合成。已经研究了取代基对其与H 2 O 2的反应性和甲基化醌（QM）形成的影响。NMR光谱和乙基乙烯基醚（EVE）捕获实验分别用于确定反应机理和QM形成。在硼酸酯的氧化裂解过程中不会产生QM，而是在生理条件下通过苯酚产物的后续转化产生的。吸电子取代基（例如芳族F，NO 2或苄基N ）促进了氧化脱硼+我3溴- ，而给电子取代基或更好的离去基团有利于QM产生。包含芳香族CH 3或OMe基团或良好离去基团（Br）的化合物可在生理条件下有效产生QM。最后，通过使用哈米特图建立了芳基硼酸酯的结构与活性之间的定量关系。现在可以预测地调整芳基硼酸/酯的反应性以及抑制或促进QM的形成。此调整很重要，因为某些应用程序可能会受益，而其他应用程序可能会受到QM生成的限制。

  DOI：

  10.1002/chem.201300539
• 作为试剂：
  描述：

  对溴甲苯 在 硼酸频哪醇酯 、 magnesium 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 42.5h， 生成 二对甲苯膦
  参考文献：
  名称：

  氧化膦可快速形成无金属的游离膦

  摘要：

  已经开发出一种在温和条件下还原仲膦氧化物的快速方法，可以简单地分离相应的游离膦。该方法涉及使用频哪醇硼烷（HBpin）的，以实现同时避免膦硼烷加合物的形成的减少，如通常与各种其它常用的甲硼烷还原剂的情况下，如硼烷四氢呋喃复合物（BH 3 ⋅THF）和硼烷二甲硫醚复合物（BH 3 ⋅SMe 2）。此外，这种方法只需要少量过量的还原剂，因此不仅可以与不需要金属助催化剂的其他硼烷还原剂进行比较，而且可以与硅烷和铝基试剂进行比较。

  DOI：

  10.1002/adsc.201800723

文献信息

• Anomalous Efficacy of Bimetallic Au/Pd Nanoclusters in C–Cl Bond Activation and Formal Metathesis-type C–B Bond Activation at Room Temperature
  作者：Raghu Nath Dhital、Hidehiro Sakurai

  DOI：10.1246/cl.2012.630

  日期：2012.6.5

  Au/Pd alloy nanoclusters stabilized by poly(N-vinylpyrrolidone) catalyze two different reactions of phenylboronic acid with 4-chlorobenzoic acid at room temperature in a single reaction cycle, cross coupling and metathesis-type homocoupling that is normally inaccessible through conventional catalysis.

  聚乙烯基吡咯烷酮稳定化的Au/Pd合金纳米团簇在室温下单反应周期内催化苯硼酸与4-氯苯甲酸进行两种不同反应：交叉耦合和通常无法通过传统催化实现的换位型均耦合反应。
• [EN] NOVEL SUBSTITUTED PYRIDO-PIPERAZINONE DERIVATIVES AS GAMMA SECRETASE MODULATORS<br/>[FR] DÉRIVÉS SUBSTITUÉS DE PYRIDO-PIPÉRAZINONE D'UN NOUVEAU TYPE EN TANT QUE MODULATEURS DE LA GAMMA-SÉCRÉTASE
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2014111457A1

  公开（公告）日：2014-07-24

  The present invention is concerned with novel substituted pyrido-piperazinone derivatives of Formula (I) wherein R1, R2, R3, R4, R5, L, Z and X have the meaning defined in the claims. The compounds according to the present invention are useful as gamma secretase modulators. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及新颖的Formula (I)中R1、R2、R3、R4、R5、L、Z和X所定义含义的取代吡啶哌唑酮衍生物。根据本发明的化合物可用作γ-分泌酶调节剂。本发明还涉及制备这种新型化合物的方法，包含该化合物作为活性成分的药物组合物，以及将该化合物用作药物的用途。
• Hydrogen Peroxide Inducible DNA Cross-Linking Agents: Targeted Anticancer Prodrugs
  作者：Yunyan Kuang、Kumudha Balakrishnan、Varsha Gandhi、Xiaohua Peng

  DOI：10.1021/ja2073824

  日期：2011.12.7

  The major concern for anticancer chemotherapeutic agents is the host toxicity. The development of anticancer prodrugs targeting the unique biochemical alterations in cancer cells is an attractive approach to achieve therapeutic activity and selectivity. We designed and synthesized a new type of nitrogen mustard prodrug that can be activated by high level of reactive oxygen species (ROS) found in cancer

  抗癌化学治疗剂的主要问题是宿主毒性。开发针对癌细胞中独特生化变化的抗癌前药是实现治疗活性和选择性的有吸引力的方法。我们设计并合成了一种新型氮芥前药，可以被癌细胞中发现的高水平活性氧 (ROS) 激活以释放活性化疗药物。通过NMR分析确定活化机制。这些前药对 ROS 的活性和选择性是通过测量 DNA 链间交联和/或 DNA 烷基化来确定的。这些化合物对各种癌细胞显示出 60-90% 的抑制作用，而正常淋巴细胞不受影响。据我们所知，
• Trapping Formaldehyde in the Homogeneous Catalytic Reduction of Carbon Dioxide
  作者：Sébastien Bontemps、Sylviane Sabo-Etienne

  DOI：10.1002/anie.201304025

  日期：2013.9.23

  Formaldehyde detectives: Evidence for the production of formaldehyde during a ruthenium‐catalyzed CO2 reduction process, and for its involvement in the formation of the resulting C2 compound, is disclosed. Ultimately, formaldehyde can be recovered by methanol trapping. HBPin=pinacolborane.

  甲醛检测剂：公开了在钌催化的CO 2还原过程中产生甲醛的证据，以及其参与生成的C 2化合物形成的证据。最终，可以通过捕集甲醇来回收甲醛。HBPin ＝频哪醇硼烷。
• The Conversion of Phenols to the Corresponding Aryl Halides Under Mild Conditions
  作者：John Huffman、Alicia Thompson、George Kabalka、Murthy Akula

  DOI：10.1055/s-2005-861791

  日期：——

  Mild, novel procedures have been developed for the syntheses of aryl halides from the corresponding phenols in modest to good yields via boronate ester intermediates.

  已经开发了温和、新颖的方法，用于通过硼酸酯中间体从相应的酚类以适度至良好的产率合成芳基卤化物。