2,6-Diisopropylphenyl group

The 2,6-diisopropylphenyl group, abbreviated Dipp, is an aromatic functional group in organic chemistry. The chemical formula can be written C6H3((CH3)2CH)2\s, but it is frequently shortened to C6H3iPr2\s, similarly to the use of C6H2Me3\s for mesityl. It offers considerable steric bulk, making it of interest for researching unstable compounds and designing ligands in organometallic chemistry. Preparation Preparation of 2,6-diisopropylphenyl compounds from 1,3-diisopropylbenzene is impractical. Steric hindrance from the isopropyl substitutents means aromatic substitution reactions will primarily produce 1,3,5-substituted benzenes (3,5-diisopropylphenyl in functional group nomenclature).November 2025 A major source of diisopropylphenyl substituents is 2,6-diisopropylaniline. Diisopropyl compounds may also be prepared from halobenzene derivatives such as 2,6-diisopropylbromobenzene.Knorr Rudolf Ruhdorfer Jakob Böhrer Petra Bronberger Hildegard Räpple Edith Sterically Congested Molecules, 11. The 2,6-Diisopropylphenyl Substituent at C=C and C=N Groups Liebigs Annalen der Chemie 1994 4 433–438 10.1002/jlac.199419940417 Applications Diisopropylphenyl substituents make up most of this NacNac ligand.|thumb The diisopropylphenyl structure consists of alkane-substituted benzene, so it is not very chemically reactive. It serves instead to provide steric hindrance, limiting reactions of other nearby functional groups. The diisopropylphenyl structure is found in many ligands calling for steric bulk. NacNac ligands can be prepared from 2,6-diisopropylaniline. Terphenyl ligands featuring two diisopropylphenyl substituents, systematically bis(diisopropylphenyl)phenyl, are capable of stabilising high-bond order compounds such as dimetallenes.Rivard Eric Power Philip P. Multiple Bonding in Heavier Element Compounds Stabilized by Bulky Terphenyl Ligands Inorganic Chemistry 2007 46 24 10047–10064 10.1021/ic700813h 17975890 The first stable digermyne was prepared using DIPP-based terphenyl ligands. Stender Matthias Phillips Andrew D. Wright Robert J. Power Philip P. Synthesis and Characterization of a Digermanium Analogue of an Alkyne Angewandte Chemie International Edition 2002 41 10 1785–1787 10.1002/1521-3773(20020517)41:10<1785::AID-ANIE1785>3.0.CO;2-6 19750717 Persistent carbenes containing 2,6-diisopropylphenyl substituents are sterically demanding Lewis bases, and can be used as chelating agents to stabilise diborenes.Mihm Cornelius Kar Sourav Sachs Andreas Duwe Dario Dewhurst Rian D. Braunschweig Holger Synthesis of symmetrical and unsymmetrical cyclic diborenes via NHC-directed C–H borylation Chemical Science 2025 16 25 11637–11643 10.1039/D5SC03150H 40463428 12127849 References Category:Aryl groups Category:Benzene derivatives