129848-99-3

Basic information

• Product Name: (3R,4S)-3-Bromo-4-hydroxy-4-phenyl-butan-2-one
• CAS NO: 129848-99-3
• Molecular Weight: 243.1
• Mol File: 129848-99-3.mol

Chemical Properties

• CAS DataBase Reference: (3R,4S)-3-Bromo-4-hydroxy-4-phenyl-butan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-3-Bromo-4-hydroxy-4-phenyl-butan-2-one(129848-99-3)
• EPA Substance Registry System: (3R,4S)-3-Bromo-4-hydroxy-4-phenyl-butan-2-one(129848-99-3)

Safety Data

• Hazardous Substances Data: 129848-99-3(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 598-31-2 1-bromoacetone 
• 1896-62-4 (E)-benzalacetone 
• 122-57-6 1-Phenylbut-1-en-3-one 

Downstream Products

• 6249-79-2 trans-2-acetyl-3-phenyloxirane 
• 6249-79-2 1-(3-phenyloxiran-2-yl)ethanone 

Relevant articles and documents

Green approach for the conversion of olefins into vic-halohydrins using N-halosuccinimides in ionic liquids

Alkenes undergo smooth bromo- and iodohydroxylation with N-bromo- and N-iodosuccinimides/water, respectively, using the air and moisture stable ionic liquid [bmim]BF4 as a novel recyclable reaction medium in high to quantitative yields. N-Halosuccinimides show enhanced reactivity in ionic liquids thereby reducing the reaction times and improving the yields considerably.

Efficient diastereoselective synthesis of anti-α-bromo-β-hydroxyketones

Anti-α-bromo-β-hydroxyketones were synthesized in high diastereoselectivity via the enolboration of a representative series of bromomethylketones using dicyclohexylboron chloride, followed by aldolization with aldehydes.

Amphiphilic Indoles as Efficient Phase-Transfer Catalysts for Bromination in Water

Brominated compounds are important, but they are usually prepared in organic solvents. Here, efficient amphiphilic indole-based phase-transfer organocatalysts were developed for environmentally benign bromination reactions in water. As test reactions, hydroxybromination of olefins and aromatic bromination could be conducted in a greener and more sustainable manner compared with methods using organic solvents, producing the corresponding bromides in good yields. Some pure products could be obtained without column chromatography.

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.

I2O5-mediated bromohydroxylation and dibromination of olefins using KBr in water

An efficient and green bromohydroxylation and dibromination of various olefins mediated by I2O5 has been developed in this work. A series of olefins gave the corresponding α-bromo-alcohols and dibromides as the major products using KBr as the brominating reagent in aqueous medium at room temperature. The diastereo- and regio-selectivities are extremely high.

Regio-and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone

An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio-and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov's rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone in CH3CN/H2O (1:1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed instantaneously.

Synthesis of bromo- And iodohydrins from deactivated alkenes by use of N-Bromo- and W-iodosaccharin

N-Bromo and N-iodosaccharin react with electron-deficient alkenes such as α,β-unsaturated ketones, acids, esters and nitriles in aqueous organic solvents, yielding the corresponding halohydrins in good yields. The reactions take place at room temperature,

A New Synthetic Method of Preparing Iodohydrin and Bromohydrin Derivatives through in Situ Generation of Hypohalous Acids from H5IO6 and NaBrO3 in the Presence of NaHSO3

Hypohydrous acids such as hypoiodous acid (IOH) and hypobromous acid (BrOH) were found to be easily generated from H5IO6 and NaBrO3 in the presence of an appropriate reducing agent such as NaHSO3.Iodohydrin and bromohydrin derivatives were synthesized in good yields from the reaction of a wide variety of organic compounds bearing carbon-carbon double bonds, with H5IO6 or NaBrO3 and NaHSO3.The iodohydroxylation of internal alkenes was achieved with high stereoselectivity to give anti products, although no stereoselectivity was observed in the bromohydroxylation of these alkenes.It was found that allylic alcohols undergo iodohydroxylation in anti-Markovnikov fashion to form iodo diols in good yields.Treatment of alkynes with H5IO6 combined with NaHSO3 afforded the corresponding ketones in fair yields, but the same treatment with NaBrO3 rather than H5IO6 produced the corresponding α,α-dibromo ketones along with small amounts of the dibromoalkenes.

SYNTHETIC CONTROL LEADING TO CHIRAL COMPOUNDS

A highly diastereoselective cross aldol reaction is developed using divalent tin enolates formed from stannous trifluoromethanesulfonate and carbonyl compounds.The reaction is extended to a highly enantioselective cross aldol reaction employing chiral dia

STEREOSELECTIVE SYNTHESIS OF CIS-α,β-EPOXYKETONES VIA DIVALENT TIN ENOLATE

A convenient method for the stereoselective synthesis of cis-β-substituted-α,β-epoxyketone is established employing Sn(OTf)2 mediated cross aldol reaction between α-bromoketone and aldehyde followed by successive treatment of the adduct with KF-dicyclohex