166330-03-6

Basic information

• Product Name: Bromomethylboronic acid, pinacol ester
• Synonyms: 2-(Bromomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 166330-03-6
• Molecular Formula: C₇H₁₄BBrO₂
• Molecular Weight: 220.91
• Product Categories: Alkyl;Organoborons;B (Classes of Boron Compounds);Boronic Acids Esters;organic boroinic acid;Organic boronic acid
• Mol File: 166330-03-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 68 °C / 6mmHg
• Flash Point: 62.8±22.6℃
• Appearance: /
• Density: 1.26
• Vapor Pressure: 1.224mmHg at 25°C
• Refractive Index: 1.4520-1.4560
• Storage Temp.: 0-10°C
• CAS DataBase Reference: Bromomethylboronic acid, pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Bromomethylboronic acid, pinacol ester(166330-03-6)
• EPA Substance Registry System: Bromomethylboronic acid, pinacol ester(166330-03-6)

Safety Data

• Hazardous Substances Data: 166330-03-6(Hazardous Substances Data)

Usage

General Description

Bromomethylboronic acid, pinacol ester is a chemical compound with the molecular formula C6H13BO3Br. It is commonly used in organic synthesis as a reagent for building carbon-carbon bonds and for its ability to form stable complexes with a variety of organic molecules. Bromomethylboronic acid, pinacol ester is a member of the boronic acid family, which are known for their versatility in chemical reactions. Bromomethylboronic acid, pinacol ester is particularly useful in Suzuki-Miyaura cross-coupling reactions, where it can be used to link two carbon atoms together. Its reactivity and selectivity make it an important tool for synthetic chemists in the development of new pharmaceuticals, agrochemicals, and materials.

InChI:InChI=1/C7H14BBrO2/c1-6(2)7(3,4)11-8(5-9)10-6/h5H2,1-4H3

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 5419-55-6 Triisopropyl borate 
• 74-95-3 1,1-dibromomethane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 137297-49-5 (bromomethyl)boronic acid bis(isopropyl)ester 

Downstream Products

• 475250-52-3 2-[(4-methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 70557-99-2 2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1478-53-1 Diethyl difluoromethylphosphonate 
• 1425747-00-7 4,4,5,5-tetramethyl-2-(3-phenylprop-2-yn-1-yl)-1,3,2-dioxaborolane 
• 1373874-65-7 (E)-2-(4,8-dimethylnona-3,7-dien-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1378427-40-7 [({(2S)-3-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]-2-methylpropyl}oxy)methyl]boronic acid 
• 1378427-39-4 [({(2R)-3-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]-2-methylpropyl}oxy)methyl]boronic acid 
• 1378427-20-3 [({3-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]propyl}oxy)methyl]boronic acid 
• 1378427-06-5 [({2-[{2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-5-[(1-methylethyl)oxy]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid 
• 1378427-26-9 [({2-[{5-cyclopropyl-2-(4-fluorophenyl)-3-[(methylamino)carbonyl]-1-benzofuran-6-yl}(methylsulfonyl)amino]ethyl}oxy)methyl]boronic acid 
• 1378868-49-5 ((2-(N-(2-(4-chlorophenyl)-5-cyclopropyl-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-6-yl)methylsulfonamido)ethoxy)methyl)boronic acid 
• 1013915-58-6 sodium 2,6-dichlorobenzyloxymethyl trifluoroborate 
• 1013915-60-0 sodium 2-chloro-4-fluorobenzyloxymethyl trifluoroborate 
• 1013915-52-0 sodium 2-chlorobenzyloxymethyl trifluoroborate 

Relevant articles and documents

Neighboring phenolic group-activated: Gem -difluoroallylboration of imines for the catalyst-free synthesis of gem -difluorohomoallylamines

We herein report an unprecedented addition reaction of pinacol gem-difluoroallylborates and imines enabled by a neighboring phenolic group in an N-protecting group under catalyst-free conditions, thus facilitating the construction of a wide range of racemic gem-difluorohomoallylamine derivatives. Based on the control experiments, a plausible transition state via the Zimmerman-Traxler model was proposed to elucidate the significance of the neighboring phenolic group, as well as the γ-selectivity of the boronate reagents.

Structure-based development of (1-(3′-Mercaptopropanamido)methyl)boronic Acid Derived Broad-Spectrum, Dual-Action Inhibitors of Metallo- And Serine-β-lactamases

The emergence and spread of bacterial pathogens acquired metallo-β-lactamase (MBL) and serine-β-lactamase (SBL) medicated β-lactam resistance gives rise to an urgent need for the development of new dual-action MBL/SBL inhibitors. Application of a pharmacophore fusion strategy led to the identification of (2′S)-(1-(3′-mercapto-2′-methylpropanamido)methyl)boronic acid (MS01) as a new dual-action inhibitor, which manifests broad-spectrum inhibition to representative MBL/SBL enzymes, including the widespread VIM-2 and KPC-2. Guided by the VIM-2:MS01 and KPC-2:MS01 complex structures, further structural optimization yielded new, more potent dual-action inhibitors. Selectivity studies indicated that the inhibitors had no apparent inhibition to human angiotensin-converting enzyme-2 and showed selectivity across serine hydrolyases in E. coli and human HEK293T cells labeled by the activity-based probe TAMRA-FP. Moreover, the inhibitors displayed potentiation of meropenem efficacy against MBL- or SBL-positive clinical isolates without apparent cytotoxicity. This work will aid efforts to develop new types of clinically useful dual-action inhibitors targeting MBL/SBL enzymes.

Br?nsted Acid Catalyzed gem-Difluoroallylation of Aldehydes and Ketone with β-Tosyloxy-γ,γ-difluroallylboronic Acid Pinacol Ester

A shelf-stable gem-difluorinated reagent β-tosyloxy-γ,γ-difluroallylboronic acid pinacol ester has been prepared, which can be easily used for the preparation of gem-difluorinated homoallylic alcohols through Br?nsted acid (PhCO2H) catalyzed ge