Related compounds Molar mass 129.25 g/mol Formula C8H19N | Density 742 kg/m³ Boiling point 127 °C Appearance Colorless liquid | |
Related amines | ||
N n diisopropylethylamine
N,N-Diisopropylethylamine, or Hünig's base, DIPEA or DIEA, is an organic compound and an amine. It is used in organic chemistry as a base. Because the nitrogen atom is shielded by the two isopropyl groups and an ethyl group only a proton is small enough to easily fit. Like 2,2,6,6-tetramethylpiperidine, this compound is a good base but a poor nucleophile, which makes it a useful organic reagent. Hünig's base is named after the German chemist Siegfried Hünig. The compound is a colourless liquid.
Contents
Hünig's base is commercially available. It is traditionally prepared by the alkylation of diisopropylamine with diethyl sulfate. If necessary, the compound can be purified by distillation from potassium hydroxide.
Non-nucleophilic base
Hünig's base was investigated for its use as a selective reagent in the alkylation of secondary amines to tertiary amines by alkyl halides. This organic reaction is often hampered by a quaternization reaction to the quaternary ammonium salt but this side-reaction is absent when Hünig's base is present.
Synthesis of scorpionine
Hünig's base forms a complex heterocyclic compound called scorpionine by a reaction with disulfur dichloride catalyzed by DABCO in a one-pot synthesis.