diisopropylamino

Diisopropylamino refers to the N,N-diisopropylamino substituent, commonly written as -N(i-Pr)2, where i-Pr stands for the isopropyl group. In this arrangement nitrogen is bonded to two isopropyl groups and to the parent molecule, giving a tertiary amine with no N–H bond. The group is bulky and moderately lipophilic due to the two isopropyl substituents.

As a tertiary amine, the diisopropylamino group behaves as a typical organic amine: it acts as a base and a nucleophile, can form ammonium salts upon protonation, and participates in N-alkylation and related transformations. The electronic effect is generally electron-donating, while steric hindrance from the isopropyl groups can slow some reactions and influence selectivity. The conjugate acid of such a group is typically in the moderately basic range, with pKa values around 9–11 for similar N,N-disubstituted amines.

Synthesis and use: The diisopropylamino substituent is introduced by alkylation of an existing amine with isopropylating agents (for example, isopropyl halides or related reagents) under appropriate basic conditions to furnish a tertiary amine. In practice, installing this bulky, lipophilic amine can be useful for tuning the basicity and steric environment of organic molecules, including ligands, catalysts, or pharmacophores, where such properties are desirable.

Safety and handling: Compounds bearing the diisopropylamino group are irritants and can be harmful if inhaled or absorbed. They should be handled with appropriate ventilation and personal protective equipment, following standard chemical-safety protocols.