18982-54-2

Basic information

• Product Name: 2-Bromobenzyl alcohol
• Synonyms: 2-BROMOBENZYL ALCOHOL;RARECHEM AL BD 0014;O-BROMOBENZYL ALCOHOL;o-Bromo Benzylalcohol 2-Bromo Benzylalcohol;2-BROMOBENZYL ALCOHOL 98%;2-Bromobenzylalkohol;2-Bromobenzylalcohol98%;Benzenemethanol, 2-bromo-
• CAS NO: 18982-54-2
• Molecular Formula: C₇H₇BrO
• Molecular Weight: 187.03
• EINECS: 242-719-4
• Product Categories: Aromatics;Benzhydrols, Benzyl & Special Alcohols;Alcohol;Alcohols;Bromine Compounds;C7 to C8;Oxygen Compounds
• Mol File: 18982-54-2.mol
• Article Data: 137

Chemical Properties

• Melting Point: 78-80 °C(lit.)
• Boiling Point: 220.79°C (rough estimate)
• Flash Point: 112.1 ºC
• Appearance: white to beige crystalline powder or needles
• Density: 1.3839 (rough estimate)
• Vapor Pressure: 0.00572mmHg at 25°C
• Refractive Index: 1.5840 (estimate)
• Storage Temp.: Store at RT.
• Solubility: DMSO, Methanol
• PKA: 13.95±0.10(Predicted)
• BRN: 2243418
• CAS DataBase Reference: 2-Bromobenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromobenzyl alcohol(18982-54-2)
• EPA Substance Registry System: 2-Bromobenzyl alcohol(18982-54-2)

Safety Data

• Hazard Codes: Xi
• Statements: 52/53-22
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 18982-54-2(Hazardous Substances Data)

Usage

Description

2-Bromobenzyl alcohol is a white to beige crystalline powder or needle-like solid that is used as an intermediate in the synthesis of various organic compounds.

Uses

Used in Microwave Assisted Palladium-Catalyzed Synthesis:
2-Bromobenzyl alcohol is used as a reactant in the microwave-assisted palladium-catalyzed synthesis of phthalides, which are important organic compounds with a wide range of applications in the pharmaceutical, agrochemical, and fragrance industries.
Used in Synthesis of 1-Hydroxy-3(1H)-1,2-Benzoboroxole:
2-Bromobenzyl alcohol is also used in the synthesis of 1-hydroxy-3(1H)-1,2-benzoboroxole, a compound with potential applications in the development of new materials and pharmaceuticals.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 3365, 1985 DOI: 10.1016/S0040-4039(00)98299-6

InChI:InChI=1/C7H7BrO/c8-7-4-2-1-3-6(7)5-9/h1-4,9H,5H2

Upstream product

• 3433-80-5 1-Bromo-2-bromomethyl-benzene 
• 88-65-3 2-bromobenzoic-acid 
• 7664-93-9 sulfuric acid 
• 601-84-3 2,6-dibromobenzoic acid 
• 109-63-7 trifluoroborane diethyl ether 
• 95-46-5 2-methylphenyl bromide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 7154-66-7 2-bromobenzoic acid chloride 
• 6091-64-1 2-bromobenzoic acid ethyl ester 
• 80070-87-7 bis(o-bromobenzyl) peroxydicarbonate 
• 933-77-7 2,7-dibromotropone 
• 27081-10-3 tropylium tetrafluoroborate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 18698-97-0 ortho-bromophenylacetic acid 

Downstream Products

• 578-51-8 2-bromobenzylchloride 
• 6630-33-7 ortho-bromobenzaldehyde 
• 208035-01-2 4-(2-bromobenzyl)phenol 
• 55549-01-4 α,α-dimethyl-o-xylene α,α'-diol 
• 17100-66-2 2-(tetrahydropyranyloxy)methylbromobenzene 
• 156642-71-6 4,5-Dimethoxy-1,2-bis(2-bromobenzyl)benzene 
• 32521-21-4 2-(Hydroxymethyl)acetophenon 
• 114468-79-0 1-amino-1,3-dihydro-1-phenylisobenzofuran 
• 15286-11-0 diethyl o-tolylphosphonate 
• 132286-87-4 (2-Bromo-benzyloxy)-tert-butyl-diphenyl-silane 
• 128346-27-0 o-(butyltelluro)benzyl alcohol 
• 89942-45-0 2-(hydroxymethyl)benzenecorbonitrile 
• 51293-49-3 α,α-diethyl-o-xylene-α,α'-diol 
• 38157-49-2 1-(o-Hydroxymethylphenyl)cycloheptanol 

Relevant articles and documents

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Silver-Catalyzed Hydroboration of C-X (X = C, O, N) Multiple Bonds

AgSbF6 was developed as an effective catalyst for the hydroboration of various unsaturated functionalities (nitriles, alkenes, and aldehydes). This atom-economic chemoselective protocol works effectively under low catalyst loading, base- A nd solvent-free moderate conditions. Importantly, this process shows excellent functional group tolerance and compatibility with structurally and electronically diverse substrates (>50 examples). Mechanistic investigations revealed that the reaction proceeds via a radical pathway. Further, the obtained N,N-diborylamines were showcased to be useful precursors for amide synthesis.

Visible Light Induced Reduction and Pinacol Coupling of Aldehydes and Ketones Catalyzed by Core/Shell Quantum Dots

We present an efficient and versatile visible light-driven methodology to transform aryl aldehydes and ketones chemoselectively either to alcohols or to pinacol products with CdSe/CdS core/shell quantum dots as photocatalysts. Thiophenols were used as proton and hydrogen atom donors and as hole traps for the excited quantum dots (QDs) in these reactions. The two products can be switched from one to the other simply by changing the amount of thiophenol in the reaction system. The core/shell QD catalysts are highly efficient with a turn over number (TON) larger than 4 × 104 and 4 × 105 for the reduction to alcohol and pinacol formation, respectively, and are very stable so that they can be recycled for at least 10 times in the reactions without significant loss of catalytic activity. The additional advantages of this method include good functional group tolerance, mild reaction conditions, the allowance of selectively reducing aldehydes in the presence of ketones, and easiness for large scale reactions. Reaction mechanisms were studied by quenching experiments and a radical capture experiment, and the reasons for the switchover of the reaction pathways upon the change of reaction conditions are provided.

The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes

In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.