2methylphenyl

2-methylphenyl is an aryl substituent derived from benzene by replacing a hydrogen at the 2-position with a methyl group. It denotes a phenyl ring that is bonded to the rest of a molecule at one carbon and bears a methyl group at the adjacent (ortho) position. The common name for this substituent is o-tolyl, and the systematic IUPAC name is 2-methylphenyl. As a substituent, its formula is C7H7.

In the series of methylphenyl substituents, 2-, 3-, and 4-methylphenyl correspond to ortho-, meta-, and para-tolyl, respectively. The 2-methylphenyl group is the ortho isomer, and its position relative to the attachment point can influence steric and electronic properties, which in turn affect reaction outcomes in aromatic substitution and cross-coupling processes.

Uses and preparation in chemistry: 2-methylphenyl is widely used as a building block in organic synthesis. It serves as the aryl moiety in biaryl compounds, dyes, pharmaceuticals, and ligands. Common methods to introduce a 2-methylphenyl group include palladium- or nickel-catalyzed cross-coupling reactions, using 2-methylphenyl halides or 2-methylphenyl boronic reagents with various partners. The group is also encountered in reagents such as aryl Grignard or organolithium derivatives under appropriate conditions.

See also: tolyl, o-tolyl; related isomers 3-methylphenyl and 4-methylphenyl.