3-Nitrobenzoic acid

The two substituents are in a meta position with respect to each other, giving the alternative name of m-nitrobenzoic acid.

[2] Since carboxylic acid functional groups are electron withdrawing, during an electrophilic aromatic substitution reaction of nitration, substituents are directed to a meta position which explains this regiochemistry.

A less efficient route involves nitration of methyl benzoate, followed by hydrolysis.

[3] Alternatively, oxidative C-C bond cleavage of 3-nitroacetophenone to the corresponding aryl carboxylic acid, has been demonstrated.

[6] The presence of both carboxylic acid and nitro functional groups deactivate the ring with respect to electrophilic aromatic substitution reactions.

Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model