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2,4,6-Collidine is used as a tissue fixative for electron microscopy. It is useful in dehydrohalogenation reactions and acts as a solvent for the cleavage of hindered esters by anhydrous lithium iodide.
Hindered base. For use in the dehydrochlorination of ɑ-chloroketones to enones, see: Org. Synth. Coll., 4, 162 (1963). For use in combination with Trifluoromethanesulfonic anhydride, A11767 for the generation of ketenimines from olefins, see N,N-Dimethylacetamide, A10924.
Superior base for peptide coupling reactions, causing less racemization than the more commonly used N-ethyldiisopropylamine or N-methylmorpholine: J. Org. Chem., 59, 695 (1994). For comparison with other hindered bases, see: J. Org. Chem., 61, 2460 (1996). For peptide reagents, see Appendix 6.
Solvent for various O-alkyl cleavage reaction by LiI, including hindered esters: J. Org. Chem., 28, 2184 (1963), and methyl ethers of phenols: Chem. Commun., 616 (1969)./n
Dufour-Gallant, J.; Chatenet, D.; Lubell, W. D. De Novo Conception of Small Molecule Modulators Based on Endogenous Peptide Ligands: Pyrrolodiazepin-2-one γ-Turn Mimics That Differentially Modulate Urotensin II Receptor-Mediated Vasoconstriction ex Vivo. J. Med. Chem. 2015, 58 (11), 4624-4637.
Fujioka, H.; Matsumoto, N.; Ohta, R.; Yamakawa, M.; Shimizu, N.; Kimura, T.; Murai, K. Organic synthesis based on the Beckmann fragmentation: generation of an electrophilic salt intermediate and successive C-C bond formation using Gilman reagents. Tetrahedron Lett. 2015, 56 (21), 2656-2658.
Gefahrenhinweise (EU): H226-H302-H311-H315-H319-H335
Flammable liquid and vapour. Harmful if swallowed. Toxic in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.