4962-45-2

Usage

Synonyms

2-(Bromomethyl)phenyl methanol
1-(Bromomethyl)-2-hydroxybenzene

Physical Properties

Color: Colorless to pale yellow
Odor: Faint
State: Liquid

Primary Uses

Intermediate in pharmaceutical production
Intermediate in dye synthesis
Intermediate in organic compound manufacturing

Function

Acts as a reagent in organic synthesis
Functions as a nucleophile in various reactions

Safety Concerns

Requires careful handling
Potentially hazardous if not used and stored properly

Upstream product

• 1196-45-8 (1-bromoethyl)benzyl bromide 
• 67-64-1 acetone 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 93-54-9 1-Phenyl-1-propanol 
• 93-55-0 1-phenyl-propan-1-one 
• 766-90-5 cis-1-phenyl-1-propylene 
• 1196-45-8 (1,2-dibromopropyl)benzene 
• 873-66-5 1-propenylbenzene 
• 637-50-3 1-phenylpropene 
• 2114-36-5 1-bromopropylbenzene 

Downstream Products

• 16735-28-7 N-(1-methyl-2-oxo-2-phenylethyl)acetamide 
• 4962-46-3 (1RS,2RS)-1-acetoxy-2-bromo-1-phenyl-propane 
• 73568-86-2 (1RS,2RS)-1-hydroxy-1-phenyl-propane-2-sulfonic acid ; sodium-salt 
• 4541-87-1 cis-1-phenylpropene oxide 
• 491-82-7 (+/-)-pseudoisoephedrine 
• 90-82-4 rac-pseudoephedrine 
• 4830-43-7 (1RS,2RS)-2-isopropylamino-1-phenyl-propan-1-ol 
• 128864-79-9 Fluoro-phenyl-acetic acid 2-bromo-1-phenyl-propyl ester 
• 128864-79-9 Fluoro-phenyl-acetic acid 2-bromo-1-phenyl-propyl ester 
• 40626-59-3 (2-Bromo-1-fluoro-propyl)-benzene 
• 40626-59-3 (2-Bromo-1-fluoro-propyl)-benzene 
• 23355-97-7 1-phenylpropylene oxide 
• 54624-37-2 (E)-(2-bromoprop-1-en-1-yl)benzene 
• 21453-89-4 (Z)-(2-bromoprop-1-en-1-yl)benzene 

Relevant academic research and scientific papers

Electrochemical bromofunctionalization of alkenes in a flow reactor

The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste production are the most persisting problems of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, thein situgeneration of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted to their corresponding dibromides, bromohydrines, bromohydrin ethers and cyclized products in good to excellent yields.

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups

The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.

Halofunctionalization of alkenes by vanadium chloroperoxidase from: Curvularia inaequalis

The vanadium-dependent chloroperoxidase from Curvularia inaequalis is a stable and efficient biocatalyst for the hydroxyhalogenation of a broad range of alkenes into halohydrins. Up to 1 200 000 TON with 69 s-1 TOF were observed for the biocatalyst. A bienzymatic cascade to yield epoxides as reaction products is presented.

On the bromination of aromatics, alkenes and alkynes using alkylammonium bromide: Towards the mimic of bromoperoxidases reactivity

This article describes an efficient method of bromination of organic substrates including aromatics, alkenes and alkynes with NH4VO3as a catalyst and H2O2as an oxidant agent using a non-toxic and easy-to-handle source of bromine, tetrabutylammonium bromide. The process was developed under mild reaction conditions and is an innovation from reported methods in aspects such as: i) short reaction times, ii) the ability to work at room temperature, iii) regioselectivity and good yields.

Catalytic transformation of esters of 1,2-azido alcohols into α-amido ketones

The esters of 1,2-azido alcohols were transformed into α-amido ketones without external oxidants through the Ru-catalyzed formation of N-H imines with the liberation of N2 followed by intramolecular migration of the acyl moiety. A wide range of α-amido ketones were obtained, and one-pot transformation into the corresponding oxazoles (or a thiazole) was demonstrated.

Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions - Synthesis of halohydrins and epoxides

β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br+ and I+ ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.

From simple organobromides or olefins to highly value-added bromohydrins: A versatile performance of dimethyl sulfoxide

A novel and efficient direct transformation of secondary bromides or olefins to highly value-added bromohydrins has been disclosed. Dimethyl sulfoxide (DMSO), a cheap and common solvent, performs its versatile role as a solvent, an essential oxidant, and also as an oxygen source in this bromohydrin synthesis.

Halogen and chalcogen cation pools stabilized by DMSO. Versatile reagents for alkene difunctionalization

Halogen and chalcogen cations (X+ = Br+, I +, ArS+, and ArSe+) were generated by low-temperature electrochemical oxidation in the presence of dimethyl sulfoxide (DMSO) and were accumulated in the solution. DFT calculations indicated that DMSO stabilizes these cations by coordination. The complexes of I+ with one and two DMSO molecules were observed by cold-spray-ionization MS analyses. The stability of the resulting cation pools of X+ increased in the order of Br+ + + +, which could be explained in terms of the electronegativity of X. The cation pools served as versatile reagents for organic synthesis; the reactions with alkenes gave β-X-substituted alkoxysulfonium ions, which were converted to the corresponding carbonyl compounds by the treatment with triethylamine, whereas the treatment with methanol gave the corresponding alcohols. The reactions with aminoalkenes and 1,6-dienes gave the cyclized products.

CF3CO2ZnEt-mediated highly regioselective rearrangement of bromohydrins to aldehydes

A highly efficient and selective rearrangement reaction of bromohydrins to aldehydes mediated by CF3CO2ZnEt was described. The secondary and tertiary aldehydes were prepared under mild conditions in good to excellent yields (85-99%). The scope and limitations of this rearrangement process were also investigated.