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2,6-Di-tert-butyl-4-methylpyridine is used for the generation of enol triflates from ketones using trifluoromethanesulfonic anhydride. It is also used in the synthesis of 1,2-dihydro-2-silanaphthalene derivatives, as base in PtCl4-catalyzed cyclization reactions of homopropargyl azide derivatives and in diastereoselective synthesis of β-thiomannopyranosides.
D Crich.; H Li. Direct stereoselective synthesis of beta-thiomannosides. Journal of Organic Chemistry. 2000, 65 (3), 801-805.
Hidekazu Arii.; Takashi Kurihara.; Kunio Mochida.; Takayuki Kawashima.Silylium ion-promoted dehydrogenative cyclization: synthesis of silicon-containing compounds derived from alkynes. Chemical Communications. 2014, 50 (50), 6649-6652.
Sterically-hindered, non-nucleophilic base.
Recommended base for the generation of enol triflates from ketones using Trifluoromethanesulfonic anhydride, A11767: J. Org. Chem., 54, 2886 (1989). For examples, see: Org. Synth. Coll., 8, 97, 126 (1993). For comparison with other hindered bases in peptide coupling reactions, see: J. Org. Chem., 61, 2460 (1996). See also Appendix 6.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.