4-氯甲基苯硼酸频哪醇酯 | 1072945-04-0

• 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-氯甲基苯硼酸频哪醇酯
• 中文别名: 4-氯甲基苯基硼酸频哪醇酯；4-氯甲基苯硼酸频那醇酯
• 英文名称: 2-(4-(chloromethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-[4-(chloromethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1072945-04-0
• 化学式: C₁₃H₁₈BClO₂
• 分子量: 252.549
• InChiKey: BCRBYHCRLQCNNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 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
• 包装等级：
  III
• 危险类别：
  8
• 危险性防范说明：
  P260,P264,P270,P280,P301+P330+P331+P310,P303+P361+P353+P310+P363,P304+P340+P310,P305+P351+P338+P310,P405,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H314,H302
• 储存条件：
  存储条件：2-8°C，建议使用惰性气体保护。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-Chloromethylphenylboronic acid, pinacol ester
Synonyms: 2-(4-(Chloromethyl)phenyl)-4,4,5,5-tetramethyl-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-Chloromethylphenylboronic acid, pinacol ester
CAS number: 1072945-04-0

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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: C13H18BClO2
Molecular weight: 252.5

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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, hydrogen chloride.

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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-氯甲基苯硼酸频哪醇酯 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四丁基碘化铵 、 sodium carbonate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 N-ethyl-5-(2-methyl-8-{[2′-(trifluoromethyl)[1,1′-biphenyl]-4-yl]methoxy}imidazo[1,2-a]pyridin-3-yl)pyridine-2-carboxamide hydrogen chloride
  参考文献：
  名称：

  Optimization and biological evaluation of imidazopyridine derivatives as a novel scaffold for γ-secretase modulators with oral efficacy against cognitive deficits in Alzheimer’s disease model mice

  摘要：

  Gamma-secretase modulators (GSMs) selectively lower amyloid-beta 42 (A beta 42) and are therefore potential disease-modifying drugs for Alzheimer's disease (AD). Here, we report the discovery of imidazopyridine derivatives as GSMs with oral activity on not only A beta 42 levels but also cognitive function. Structural optimization of the biphenyl group and pyridine-2-amide moiety of compound 1a greatly improved GSM activity and rat microsomal stability, respectively. 5-{8-[(3,4'-Difluoro[1,1'-biphenyl]-4-yl)methoxy]-2-methylimidazo[1,2-a]pyridin3-yl}-N-methylpyridine-2-carboxamide (1o) showed high in vitro potency and brain exposure, induced a robust reduction in brain A beta 42 levels, and exhibited undetectable inhibition of cytochrome p450 enzymes. Moreover, compound 1o showed excellent efficacy against cognitive deficits in AD model mice. These findings suggest that compound 1o is a promising candidate for AD therapeutics.

  DOI：

  10.1016/j.bmc.2020.115455
• 作为产物：
  描述：

  4-(羟甲基)苯硼酸频哪醇酯 在 N,N'-二甲基硫脲 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以63%的产率得到4-氯甲基苯硼酸频哪醇酯
  参考文献：
  名称：

  硫脲介导的醇卤化反应。

  摘要：

  提出了在亚化学计量的硫脲添加剂的存在下加速的在温和条件下醇的卤化。硫脲的添加量决定了反应的途径，该途径可能与所需的卤化反应不同，在没有硫脲的情况下朝着醇的氧化，或者在使用过量的硫脲时朝着原料的回收。溴化和氯化对于伯醇，仲醇，叔醇和苄醇都非常有效，并且可以耐受各种官能团。详细的电子顺磁共振（EPR）研究，同位素标记和其他对照实验表明，基于自由基的机理。反应是在环境条件下进行的，使用的试剂普遍存在且价格便宜，具有广泛的应用范围，并且可以实现高度原子经济，

  DOI：

  10.1021/acs.joc.0c01431

文献信息

• Copper-catalyzed sp3-sp3 cross-coupling of turbo grignards with benzyl halides
  作者：Greg Petruncio、Synah Elahi-Mohassel、Michael Girgis、Mikell Paige

  DOI：10.1016/j.tetlet.2021.153516

  日期：2021.12

  benzyl halides and sulfonates imparts unique reactivity at the benzylic carbon atom. Photoredox sp3-sp3 cross-coupling proved ineffective for coupling p-methoxybenzyl chloride (PMBCl), leading to a new strategy for the sp3-sp3 cross-coupling of benzyl halides and sulfonates. This strategy involved LiCl-accelerated synthesis of a Grignard reagent followed by a copper-catalyzed cross-coupling. The conditions

  苄基卤化物和磺酸盐中的芳环赋予苄基碳原子独特的反应性。Photoredox sp 3 -sp 3交叉偶联被证明对偶联对甲氧基苄基氯 (PMBCl)无效，导致了苄基卤化物和磺酸盐的 sp 3 -sp 3交叉偶联的新策略。该策略涉及 LiCl 加速格氏试剂的合成，然后是铜催化的交叉偶联。由于 PMBCl 的特殊反应性，该条件对 PMBCl 工作良好，但其他苄基溴或磺酸盐反应不佳。
• A visible-light mediated three-component radical process using dithiocarbamate anion catalysis
  作者：Sara Cuadros、Matthew A. Horwitz、Bertrand Schweitzer-Chaput、Paolo Melchiorre

  DOI：10.1039/c9sc00833k

  日期：——

  We report a photoinduced three-component radical process, which couples readily available alkyl chlorides, maleimides, and heteroaromatic fragments to rapidly generate complex chiral products with high diastereocontrol. This method generates radicals via an SN2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the precursors. It therefore grants access to open-shell

  我们报告了光诱导的三组分自由基过程，该过程耦合随时可用的烷基氯化物，马来酰亚胺和杂芳族片段，以快速生成具有高非对映异构控制性的复杂手性产物。该方法通过基于S N 2的光化学催化机理产生自由基，这不依赖于前体的氧化还原性质。因此，它可以从底物中获得与经典自由基产生策略不相容或惰性的底壳中间体。该过程的氧化还原中性条件使其对氧化还原敏感的底物具有耐受性，并允许在级联产物中安装多个生物学相关的杂环。
• Efficient Synthesis of Aryl Boronates via Cobalt-Catalyzed Borylation of Aryl Chlorides and Bromides
  作者：Piyush Kumar Verma、Souvik Mandal、K. Geetharani

  DOI：10.1021/acscatal.8b00536

  日期：2018.5.4

  An efficient catalytic system based on a Co(II)-NHC precursor has been developed for the cross coupling of bis(pinacolato)diboron with aryl halides including aryl chlorides, affording the aryl boronates in good to excellent yields. A wide range of functional groups are tolerated under mild reaction conditions. The reaction shows excellent chemoselectivity for bromide over chloride. Preliminary mechanistic

  已经开发了基于Co（II）-NHC前体的有效催化体系，用于双（频哪醇）二硼与芳基卤化物（包括芳基氯化物）的交叉偶联，从而提供了高至优异收率的硼酸芳基酯。在温和的反应条件下可以耐受多种官能团。该反应对溴的氯化物显示出优异的化学选择性。初步的机理研究表明，催化循环可能依赖于钴（I）-（III）氧化还原对。
• [EN] BETA-LACTAM COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE BÊTA-LACTAME ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV HONG KONG

  公开号：WO2020057592A1

  公开（公告）日：2020-03-26

  Beta-lactam compounds to detect carbapenemases or microbial carbapenem resistance are disclosed. The compounds contain a chemical probe. Upon hydrolysis by carbapenemases, the compounds undergo intramolecular rearrangement and release the chemical probe. Detection of the released chemical probe indicates the presence of carbapenemases and the presence of microbial carbapenem resistance.

  本文披露了用于检测碳青霉烯酶或微生物对碳青霉烯的抗性的β-内酰胺化合物。这些化合物含有化学探针。在碳青霉烯酶的水解作用下，这些化合物会发生分子内重排并释放出化学探针。检测释放的化学探针表明存在碳青霉烯酶和微生物对碳青霉烯的抗性。
• 6H-IMIDAZO[1,5-a]PYRROLO[2,3-e]PYRAZINE COMPOUNDS
  申请人：Breinlinger Eric

  公开号：US20140315883A1

  公开（公告）日：2014-10-23

  The invention provides a compound of Formula (I as defined herein, pharmaceutically acceptable salts, pro-drugs, biologically active metabolites, stereoisomers and isomers thereof wherein the variables are defined herein. The compounds of the invention are useful for treating immunological and oncological conditions.

  该发明提供了一种符合本处定义的化合物的化学式(I)，包括药用盐、前药、生物活性代谢物、立体异构体和同分异构体，其中变量在本处定义。该发明的化合物可用于治疗免疫和肿瘤病症。