51901-85-0

Basic information

• Product Name: 2-BROMO-1,3,2-BENZODIOXABOROLE
• Synonyms: B-BROMOCATECHOLBORANE;2-BROMO-1,3,2-BENZODIOXABOROLE;beta-Bromocatecholborane;2-bromo-1,3,2-benzodioxaborale;1,3,2-Benzodioxaborole, 2-bromo-;2-Bromo-1,3,2-benzodioxaborole,B-Bromocatechol-borane;2-broMobenzo[d][1,3,2]dioxaborole;2-Bromo-1,3,2-benzodioxaborole 97%
• CAS NO: 51901-85-0
• Molecular Formula: C₆H₄BBrO₂
• Molecular Weight: 198.81
• Product Categories: B (Classes of Boron Compounds);B-Bromocatecholborane, etc.
• Mol File: 51901-85-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: 51-53 °C(lit.)
• Boiling Point: 76 °C9 mm Hg(lit.)
• Flash Point: 107 °F
• Appearance: /
• Density: 1.67g/cm³
• Vapor Pressure: 0.346mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: −20°C
• BRN: 2445073
• CAS DataBase Reference: 2-BROMO-1,3,2-BENZODIOXABOROLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1,3,2-BENZODIOXABOROLE(51901-85-0)
• EPA Substance Registry System: 2-BROMO-1,3,2-BENZODIOXABOROLE(51901-85-0)

Safety Data

• Hazard Codes: C
• Statements: 14-34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2925 4.1/PG 2
• WGK Germany: 3
• F: 8-10-21
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 51901-85-0(Hazardous Substances Data)

Usage

Purification Methods

Keep at 20o/15mm for some time and then fractionally distil. [Gerrard J Chem Soc 1529 1959, Beilstein 6 IV 5612.]

InChI:InChI=1/C6H4BBrO2/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H

Upstream product

• 161470-27-5 1-methoxy-2-(2-phenylethoxy)benzene 
• 835-79-0 1-(benzyloxy)-2-methoxybenzene 
• 57100-59-1 (o-C₆H₄O₂)BSH 

Downstream Products

• 193978-23-3 2-thiopheneboronic acid pinacol ester 
• 195062-61-4 4-chlorophenylboronic acid pinacol ester 
• 214360-65-3 4-trifluoromethylphenylboronic acid pinacol ester 
• 171364-80-0 methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 171364-81-1 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone 
• 214360-70-0 4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane 
• 171364-82-2 4-cyanophenylboronic acid pinacol ester 
• 190788-58-0 4,4,5,5-tetramethyl-2-(4-methylsulfanylphenyl)-[1,3,2]-dioxaborolane 
• 195062-62-5 ethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 214360-48-2 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 
• 269410-00-6 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzoic acid ethyl ester 
• 32999-10-3 2-butyl-1,3,2-benzodioxaborole 
• 210970-73-3 2-[di(benzenesulfonyl)amino]-benzo-1,3,2-dioxaborol 

Relevant articles and documents

BBr3-Assisted Preparation of Aromatic Alkyl Bromides from Lignin and Lignin Model Compounds

For the first time, BBr3-assisted nucleophilic substitution was applied to a variety of β-O-4 and α-O-4 model compounds for the highly effective cleavage of different C-O bonds, including C-Oα-OH, Cβ-O/Cα-O and CMe-O bonds (99% conversion for most cases). Without any pretreatment, the substitution proceeds at room temperature in the absence of any catalyst, or additive, selectively affording phenols and important organic synthesis reagents, aromatic alkyl bromides, in high to excellent yields (up to 98%). Preliminary studies also highlight the prospect of this method for the effective cleavage of different types of C-O bonds in real lignin. A total 14 wt % yield of aromatic alkyl bromide, 4-(1,2-dibromo-3-hydroxypropyl)benzene-1,2-diol (10), has been obtained from an extracted lignin through this method.