N,N-Dimethylaniline (NNDMA)

Introduction

N,N-Dimethylaniline (NNDMA, CAS: 121-69-7, Scheme [1]) is colorless liquid with a boiling point of 193–194 °C. It is a simple but widely applied reagent. It is not only used as a starting material in the synthesis of dyestuffs, pharmaceuticals, agrochemicals, and fine chemicals, but also used as a solvent, stabilizer, and analytical reagent.[1] The low price of NNDMA (due to the industrial production) has played an important role for its applications.

Scheme 1

In its original applications, NNDMA was used as a solvent, in electrophilic substitutions on the para-position of the benzene ring, and to prepare quaternary amines. However, in recent years, researchers have paid more and more attention to developing further applications, such as the reactions on the methyl groups attached to the nitrogen atom. According to the literature published in the last years, NNDMA can react with alkenes, alkynes, active methylenes, and cyano groups. By C–C and C–N bond activation of NNDMA, nitrogen compounds can be constructed with reagents containing active hydrogens, and NNDMA can be used to prepare heterocyclic compounds by coupling reactions.

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