N,N-Diisopropylethylamine

[3] DIPEA is a sterically hindered organic base that is commonly employed as a proton scavenger.

This is often hampered by an unwanted Menshutkin reaction forming a quaternary ammonium salt, but is absent when DIPEA is present.

[7] Although triethylamine is traditionally employed as the hindered base in Swern oxidations, the structurally similar DIPEA can be used instead, as exemplified below.

[8] DIPEA forms a complex heterocyclic compound called scorpionine (bis([1,2]dithiolo)-[1,4]thiazine) upon reaction with disulfur dichloride that is catalyzed by DABCO in a one-pot synthesis.

[9] DIPEA and triethylamine are structurally very similar, with both compounds considered hindered organic bases.

Skeletal formula of N,N-diisopropylethylamine
Skeletal formula of N,N-diisopropylethylamine