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2-Chloro-4,6-dimethoxy-1,3,5-triazine is used as a peptide coupling agent for the purification of peptides. It is used in the synthesis of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride through coupling with N-methylmorpholine in tetrahydrofuran. Further, it plays an important role in the production of bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether, through reaction with 2-hydroxy-4,6-dimethoxy-1,3,5-triazine. In addition to this, it is involved in the preparation of 2-(4,6-dimethoxy-1,3,5-triazinyl)trialkylammonium salts through reaction with various tertiary amines.
Reagent for activation of carboxylic acids to nucleophiles: J. Org. Chem., 63, 4248 (1998). Peptide coupling reagent: Synthesis, 917 (1987). With N-methylmorpholine forms the quaternary chloride (DMTMM) which is a valuable low-cost coupling agent in solid-phase peptide synthesis: Synlett, 275 (2000). For a reexamination of the use of the reagent in peptide coupling, see: Tetrahedron Lett., 42, 4161 (2002); see also Appendix 6.
Similarly, carboxylic acids are converted to Weinreb amides by reaction with N,O-dialkyl hydroxylamines: J. Org. Chem., 66, 2534 (2001).
Can also be used for the esterification of carboxylic acids: Synthesis, 593 (1999). The intermediate active esters can be hydrogenolyzed, providing a simple method for reduction of acids to aldehydes; at higher pressures, further reduction to the alcohol can be effected: J. Org. Chem., 64, 8962 (1999).
Iranpoor, N.; Panahi, F.; Jamedi, F. Nickel-catalyzed one-pot synthesis of biaryls from phenols and arylboronic acids via C-O activation using TCT reagent. J. Organomet. Chem. 2015, 781, 6-10.
Duangkamol, C.; Jaita, S.; Wangngae, S.; Phakhodee, W.; Pattarawarapan, M. Catalytic role of PPh3 and its polymer bound analog in the amidation of carboxylic acids mediated by 2,4,6-trichloro-1,3,5-triazine. Tetrahedron Lett. 2015, 56 (35), 4997-5001.
Gefahrenhinweise (EU): H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
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.