13664-98-7

Basic information

• Product Name: 2,2-DIBROMO-1-P-TOLYLETHANONE
• Synonyms: 2,2-DIBROMO-1-P-TOLYLETHANONE;2,2-dibromo-1-(4-methylphenyl)ethanone
• CAS NO: 13664-98-7
• Molecular Formula: C₉H₈Br₂O
• Molecular Weight: 291.97
• Mol File: 13664-98-7.mol
• Article Data: 45

Chemical Properties

• Melting Point: 97-98 °C
• Boiling Point: 290.3±25.0 °C(Predicted)
• Appearance: /
• Density: 1.780±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2,2-DIBROMO-1-P-TOLYLETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DIBROMO-1-P-TOLYLETHANONE(13664-98-7)
• EPA Substance Registry System: 2,2-DIBROMO-1-P-TOLYLETHANONE(13664-98-7)

Safety Data

• Hazardous Substances Data: 13664-98-7(Hazardous Substances Data)

Usage

General Description

2,2-DIBROMO-1-P-TOLYLETHANONE is a chemical compound that belongs to the group of benzyl ketones. It is a white to light yellow crystalline solid with a molecular formula of C9H8Br2O. 2,2-DIBROMO-1-P-TOLYLETHANONE is commonly used in organic synthesis and as a building block for the preparation of other compounds. It is also a useful intermediate in the production of pharmaceuticals, dyes, and other organic substances. 2,2-DIBROMO-1-P-TOLYLETHANONE is a potentially hazardous chemical and should be handled with caution, as it may cause skin and eye irritation and should be stored in a cool, dry place away from direct sunlight and heat sources.

Upstream product

• 122-00-9 para-methylacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 766-97-2 4-n-methylphenylacetylene 
• 104-87-0 4-methyl-benzaldehyde 
• 93979-10-3 1-(p-methylphenyl)-2,2,2-tribromoethanol 
• 7559-36-6 4-methyl-β-nitrostyrene 
• 18103-98-5 3-dimethylamino-1-(4-methyl-phenyl)-2-propen-1-one 
• 536-50-5 CH₃C₆H₄CH(CH₃)OH 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 74-95-3 1,1-dibromomethane 
• 2089-33-0 4-methylacethophenone oxime 
• 108-88-3 toluene 
• 67-66-3 chloroform 

Downstream Products

• 99-94-5 p-Toluic acid 
• 1068459-70-0 2-bromo-2-p-tolylpent-4-enal 
• 34966-53-5 methyl 4-methylphenylglyoxylate 
• 1357932-22-9 3-hydroxypropyl 2-oxo-2-p-tolylacetate 
• 1357932-85-4 propane-1,3-diyl bis (2-oxo-2-p-tolylacetate) 
• 1284150-89-5 N-(2-(1H-indol-3-yl)ethyl)-2-oxo-2-(p-tolyl)acetamide 
• 881597-49-5 N-(2-(1H-indol-3-yl)ethyl)-4-methylbenzamide 
• 61820-95-9 2-(toluene-4-sulfonyl)-1-p-tolylethanone 
• 17565-28-5 p-tolyl-glyoxal-bis-phenylhydrazone 
• 17286-62-3 2-(4-methylphenyl)quinoxaline 
• 120116-88-3 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide 

Relevant articles and documents

A H2O2/HBr system-several directions but one choice: oxidation-bromination of secondary alcohols into mono- or dibromo ketones

In this work we found that a H2O2-HBr(aq) system allows synthesis of α-monobromo ketones and α,α′-dibromo ketones from aliphatic and secondary benzylic alcohols with yields up to 91%. It is possible to selectively direct the process toward the formation of mono- or dibromo ketones by varying the amount of hydrogen peroxide and hydrobromic acid. The convenience of application, simple equipment, multifaceted reactivity, and compliance with green chemistry principles make the application of the H2O2-HBr(aq) system very attractive in laboratories and industry. The proposed oxidation-bromination process is selective in spite of known properties of ketones to be oxidized by the Baeyer-Villiger reaction or peroxidated with the formation of compounds with the O-O moiety in the presence of hydrogen peroxide and Bronsted acids.

Reactivity of substrates with multiple competitive reactive sites toward NBS under neat reaction conditions promoted by visible light

Regioselectivity of visible-light-induced transformations of a range of (hetero)aryl alkyl-substituted ketones bearing several competitive reactive sites (α-carbonyl, benzyl and aromatic ring) with N-bromosuccinimide (NBS) was studied under solvent-free reaction conditions (SFRC) and in the absence of inert-gas atmosphere, radical initiators and catalysts. An 8-W energy-saving household lamp was used for irradiation. Heterogeneous reaction conditions were dealt with throughout the study. All substrates were mono- or dibrominated at the α-carbonyl position, and additionally, some benzylic or aromatic bromination was observed in substrates with benzylic carbon atoms or electron-donating methoxy groups, respectively. Surprisingly, ipso-substitution of the acyl group with a bromine atom took place with (4-methoxynaphthyl) alkyl ketones. While the addition of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidin-1-yloxy) decreased the extent of α- and ring bromination, it completely suppressed the benzylic bromination and α,α-dibromination with NBS under SFRC.

Selective Debromination of α,α,α-Tribromomethylketones with HBr–H2O Reductive Catalytic System

A debromination of α,α,α-tribromomethylketones is developed for chemoselective synthesis of α-mono- and α,α-dibromomethylketones with high selectivity under H2O–HBr reductive conditions. This method offers an efficient and direct way to synthesize α-mono or α,α-dibromomethylketone compounds in high to excellent yields through the process of HBr self-circulation in water.