54757-29-8

Basic information

• Product Name: Benzene, 2-(bromomethyl)-1,3,4-trimethyl-
• CAS NO: 54757-29-8
• Molecular Formula: C10H13Br
• Molecular Weight: 213.117
• Mol File: 54757-29-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzene, 2-(bromomethyl)-1,3,4-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 2-(bromomethyl)-1,3,4-trimethyl-(54757-29-8)
• EPA Substance Registry System: Benzene, 2-(bromomethyl)-1,3,4-trimethyl-(54757-29-8)

Safety Data

• Hazardous Substances Data: 54757-29-8(Hazardous Substances Data)

Upstream product

• 77743-10-3 (2,5,6-trimethylbenzyl)bis(dimethylglyoximato)pyridinecobalt(III) 
• 75-62-7 Bromotrichloromethane 
• 488-23-3 1,2,3,4-Tetramethylbenzene 
• 7726-95-6 bromine 

Downstream Products

• 854830-49-2 (2,3,6-trimethyl-benzyl)-malonic acid 
• 18237-73-5 (2,3,6-trimethylphenyl)methyl alcohol 
• 2529-36-4 2,3,6-trimethylbenzoic acid 
• 86361-13-9 (bicyclo<2.2.1>heptene-5 yle-2)-1 methyl-1 (trimethyl-2,3,6 phenyl)-3 propanol-1, endo 
• 86361-13-9 (bicyclo<2.2.1>heptene-5 yle-2)-1 methyl-1 (trimethyl-2,3,6 phenyl)-3 propanol-1, exo 
• 86361-13-9 (bicyclo<2.2.1>heptene-5 yle-2)-1 methyl-1 (trimethyl-2,3,6 phenyl)-3 propanol-1 
• 58720-40-4 4-(2,3,6-trimethyl-phenyl)-butan-2-one 
• 86361-11-7 (bicyclo<2.2.1>heptene-5 yle-2)-1 (trimethyl-2,3,6 phenyl)-3 propanone-1, endo 
• 86361-11-7 (bicyclo<2.2.1>heptene-5 yle-2)-1 (trimethyl-2,3,6 phenyl)-3 propanone-1, exo 
• 86361-11-7 (bicyclo<2.2.1>heptene-5 yle-2)-1 (trimethyl-2,3,6 phenyl)-3 propanone-1 
• 18237-71-3 acetic acid-(2,3,6-trimethyl-benzyl ester) 
• 854821-92-4 (2,3,6-trimethyl-benzyl)-malonic acid diethyl ester 
• 59700-21-9 methyl-3 (trimethyl-2,3,6 phenyl)-5 pentene-1 ol-3 

Relevant articles and documents

Nuclear versus Side-Chain Bromination of Methyl-Substituted Anisoles by N-Bromosuccinimide

The reactions of methyl-substituted anisoles with N-bromosuccinimide in CCl4 are reported.In the absence of a catalyst and under irradiation, some of these substrates undergo nuclear bromination in competition with the well-known side-chain bromination.With 2-methylanisole and with 2,6-dimethylanisole, nuclear bromination is not observed, whereas with 3,5-dimethylanisole, nuclear bromination at the 4-position is the dominating reaction.Investigation of the reactivity of several other methyl-substituted anisoles revealed the following general trend: methyl-substituted anisoles are attacked at the position para to the methoxy group rather than at the side chain when (at least) two methyl groups are present at positions 3 and 5.When positions 2 and 6 are both occupied, nuclear bromination is retarded; in 2,6-dimethylanisole and 2,3,6-trimethylanisole, only side-chain bromination is observed.In contrast, in 2,3,5,6-tetramethylanisole, the 4-position is sufficiently reactive to be brominated, because the decrease in reactivity by the presence of two methyl groups at positions 2 and 6 is overruled by the two additional methyl groups at positions 3 and 5; as a result, both nuclear and side-chain bromination occur.The observed chemospecificity can be rationalized by a difference in mechanism: the side-chain bromination is radical reaction, while the nuclear bromination is an electrophilic aromatic substitution reaction, which is so far contrary to expectation, as irradiation had been expected to favor radical processes.

HOMOLYTIC DISPLACEMENT AT CARBON VI. SYNTHESIS OF TRICHLOROETHYLARENES FROM BENZYLCOBALOXIMES

Benzylbis(dimethylglyoximato)pyridinecobalt(III) reacts with bromotrichloromethane at from 50 to 90 deg C in chloroform to give good yields of trichloroethylbenzene, which are higher when imidazole is present in the reaction mixture.Methyl- and polymethyl-substituted benzylbis(dimethylglyximato)pyridinecobalt(III) complexes give higher yields of the corresponding trichloroethylarenes (85-90percent), whereas 4-chlorobenzylbis(dimethylglyoximato)pyridinecobalt(III) only gives the 4-nitro-trichloroethylarene when imidazole is present during the reaciton.Similar reactions were observed with benzylcobaloximes and trichloromethanesulphonyl chloride both thermally and under irradiation by tungsten lamps through all-pyrex apparatus.The reactions are interpreted as a direct attack of the trichloromethyl radical on the α-carbon of the benzyl ligand.