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2,6-Lutidine is used as a solvent in organic synthesis and as a sterically hindered mild base. It is also used as a vulcanization accelerator for dyes, resins and rubber. It also acts as a food additive.
This hindered base has been recommended for the exhaustive methylation of aromatic amines: J. Org. Chem., 35, 1558 (1970), and for the Rosenmund reduction of acyl halides to aldehydes: Synthesis, 767 (1976).
Base catalyst for the silylation of highly-hindered secondary or tertiary alcohols by tert-Butyldimethylsilyl trifluoromethanesulfonate, A12174.
For monometallation with potassium amide in liquid ammonia, and subsequent carboethoxylation with diethyl carbonate, see: Org. Synth. Coll., 6, 611 (1988)./
Timmiatia, S. N.; Jalila, A. A.; Triwahyono, S.; Setiabudi, H. D.; Annuar, N. H. R. Formation of acidic Brönsted (MoOx)-(Hy)+ evidenced by XRD and 2,6-lutidine FTIR spectroscopy for cumene cracking. Appl. Catal., A2013, 459, 8-16.
Geoghegan, K.; Bode, J. W. Bespoke SnAP Reagents for the Synthesis of C-Substituted Spirocyclic and Bicyclic Saturated N-Heterocycles. Org. Lett. 2015, 17 (8), 1934-1937.
Hanson, S. K.; Baker, R. T. Knocking on Wood: Base Metal Complexes as Catalysts for Selective Oxidation of Lignin Models and Extracts. Acc. Chem. Res. 2015,48 (7), 2037-2048.
Gefahrenhinweise (EU): H226-H302-H315-H319-H335
Flammable liquid and vapour. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Wear protective gloves/clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.