33994-13-7

Basic information

• Product Name: 1-Propanone, 3-bromo-1-(4-bromophenyl)-
• CAS NO: 33994-13-7
• Molecular Formula: C9H8Br2O
• Molecular Weight: 291.97
• Mol File: 33994-13-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1-Propanone, 3-bromo-1-(4-bromophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 3-bromo-1-(4-bromophenyl)-(33994-13-7)
• EPA Substance Registry System: 1-Propanone, 3-bromo-1-(4-bromophenyl)-(33994-13-7)

Safety Data

• Hazardous Substances Data: 33994-13-7(Hazardous Substances Data)

Usage

Structure

A derivative of acetone with a bromine atom attached to the third carbon atom in the propanone chain and a 4-bromophenyl group attached to the first carbon atom.

Usage

Primarily used as an intermediate in the synthesis of pharmaceuticals and other organic chemicals, as well as in the production of herbicides and insecticides.

Importance

A powerful and versatile building block in organic chemistry, widely used in the production of various compounds with diverse applications in the chemical industry.

Upstream product

• 109240-30-4 1-(4-bromophenyl)cyclopropan-1-ol 
• 10342-83-3 4'-Bromopropiophenone 
• 38786-67-3 2-bromo-1-(4-bromophenyl)propan-1-one 
• 108-86-1 bromobenzene 
• 15486-96-1 3-Bromopropionyl chloride 

Downstream Products

• 33994-21-7 1-bromo-4-(3-bromo-1-chloropropyl)benzene 
• 54287-94-4 3-(4'-bromophenyl)-1-methylpyrazole 
• 1453810-94-0 C₁₄H₁₅BrO₅ 
• 1453811-05-6 dimethyl 2-(4-bromobenzoyl)cyclopropane-1,1-dicarboxylate 
• 509083-38-9 3-bromo-1-(4-bromophenyl)propan-1-ol 
• 92905-62-9 6-(4-bromo-phenyl)-3,5-dimethyl-2-nitro-imidazo[2,1-b]thiazole 
• 92697-08-0 6-(4-bromo-phenyl)-3,5-dimethyl-imidazo[2,1-b]thiazole 

Relevant articles and documents

Electrochemical Synthesis of 2-Bromoethyl and 2-Iodoethyl Ketones from Cyclopropanols

A simple electrochemical protocol for the preparation of 2-bromoethyl- and 2-iodoethyl ketones from cyclopropanols and magnesium halides has been developed. The reaction proceeded with exclusive regioselectivity and without epimerization of the α-stereocenter in the products. We also showed that the synthesized diastereomerically pure 2-bromoethyl ketones undergo smooth copper and nickel-catalyzed alkylation, alkenylation, and arylations reactions.

Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.

Anodic cyclization of dimethyl 2-(3-Oxo-3-arylpropyl) malonates into the corresponding dimethyl 2-aroylcyclopropane-1,1-dicarboxylates

A variety of dimethyl 2-(3-oxo-3-arylpropyl)malonates were electrooxidized in methanol, in the presence of potassium iodide and a base or a neutral salt, to give the corresponding cyclized dimethyl 2-aroylcyclopropane-1,1- dicarboxylates in moderate to good yields. The reactions were carried out under extremely mild reaction conditions, in which the optimal amount of electrolytic current varied from 2.12-2.41 F·mol-1 depending on the substrates. The reaction presumably proceeds via a two-electron oxidation process, in which iodide ions play an important role as the electron carrier between the anode and the substrate. Georg Thieme Verlag Stuttgart. New York.