51134-60-2

Usage

InChI:InChI=1/C8H15BrO/c1-3-4-5-6-8(9)7(2)10/h8H,3-6H2,1-2H3

Upstream product

• 122-56-5 tributyl borane 
• 78-94-4 methyl vinyl ketone 
• 18402-82-9 (3E)-oct-3-en-2-one 
• 108-22-5 Isopropenyl acetate 
• 111-13-7 hexyl-methyl-ketone 
• 67810-87-1 2-Octyl benzyl ether 
• 4128-31-8 rac-octan-2-ol 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 21894-17-7 2r-chloro-3c-methyl-2-pentyl-oxirane 

Downstream Products

• 111-13-7 hexyl-methyl-ketone 
• 146329-67-1 (R)-3-Hydroxy-2-octanone 
• 86838-20-2 (+)-(3S)-3-hydroxyoctan-2-one 
• 21419-30-7 hydrochloride salt of 3-amino-2-octanone 

Relevant academic research and scientific papers

SYNTHESIS OF IMIDAZOLES

Silica gel was found to facilitate the conversion of 3-bromo-2-alkanones to imidazoles by the action of formamide.The selective 3-bromination of 2-alkanones was carried out in ethyl acetate.

Catalytic dehydrogenative dual functionalization of ethers: Dealkylation-oxidation-bromination accompanied by C-O bond cleavage: Via aerobic oxidation of bromide

Catalytic dehydrogenative dual functionalization (DDF) of ethers via oxidation, dealkylation, and α-bromination by the aerobic oxidation of bromide was developed to obtain the corresponding α-bromo ketones in high yields. In particular, the reaction of substituted tetrahydrofurans as cyclic ethers provided 3,3-dibromo tetrahydrofuran-2-ols in high yields selectively through the double α-bromination.

Solvent-free oxidation of aliphatic alcohols with ceric ammonium nitrate-lithium bromide system

Esters are formed during the solvent-free oxidation of primary aliphatic C5-C9 alcohols with Ce(NH4)2(NO 3)6-LiBr, whereas secondary octan-2-ol gives a mixture of isomeric 1-and 3-bromooctan-2-ones.

Chemoenzymatic synthesis of 'α-bichiral' synthons. Application to the preparation of chiral epoxides

Microbiological reduction of 3-bromo-2-octanone and 3-azido-2-octanone led to all the stereoisomers of 3-bromo-2-octanol and 3-azido-2-octanol. Chiral 2,3-epoxyoctanes were prepared from the 3-bromo-2-octanols.

SYNTHESIS OF 4-IMIDAZOLIN-2-ONES

The reaction of α-bromoketones with CO(NH2)2 and AcONH4 in aqueous acetic acid gave substituted 4-imidazolin-2-ones.

4,3-ADDITIONS TO α,β-UNSATURATED KETONES VIA η2 C=C BINDING TO A RUTHENIUM COMPLEX.

The *Ru(CO)2>+ fragment (Cp* = η5-C5Me5) binds α,β-unsaturated ketones in an η2-C=C fashion.The resulting complex is subject to attack by H- at the 4-position, leaving the ruthenium bound to the substrate at the 3-position.The Ru-C bond, formed in this way, can be cleaved to give a variety of 4,3-addition products.

REACTION OF ALDEHYDES AND KETONES WITH t-BUTYL BROMIDE-DIMETHYL SULPHOXIDE

Reacting aldehydes and ketones with the "ButBr-Me2SO" system produces the corresponding α-bromoderivatives 2.In the case of ketones, where more than one regioisomer is possible, bromination is obtained exclusively at the more highly substituted α-position.With slight modifications of the reaction conditions (addition of Me2S, Me2SO) it is possible to obtain "in situ" formation of either dimethyl(2-oxo-phenylalkyl)sulphonium salts 3 or of α-methylthioderivatives 4.Dimethyl(1-methyl-2-oxo-2-phenylethyl)sulphonium bromide (3h) during crystallization undergoes spontaneous resolution of the two enantiomers, as demonstrated by single crystal X-ray analysis and absolute configuration assignment.