CDMT | CAS 3140-73-6 | ≥98%

CDMT — 2-chloro-4,6-dimethoxy-1,3,5-triazine — is a triazine-based condensing reagent for amide, ester and peptide bond formation in solution. With a tertiary amine base such as N-methylmorpholine (NMM), it activates carboxylic acids through a 2-acyloxy-4,6-dimethoxy-1,3,5-triazine active ester, which is then aminolysed or alcoholysed in the same pot to give amides or esters. The same activation chemistry underlies DMTMM, the pre-formed triazinylammonium coupling salt obtained from CDMT and NMM. CDMT is supplied as a white crystalline solid, soluble in many organic solvents; it is moisture-sensitive and should be stored dry.

Common Scientific Applications

• Amide bond formation (CDMT/NMM): CDMT and a tertiary amine base, typically N-methylmorpholine, convert a carboxylic acid into a 2-acyloxy-4,6-dimethoxytriazine active ester that is aminolysed in situ, giving the amide in a one-pot procedure.
• Peptide synthesis: couples N-protected amino acids in solution under mild conditions, with low epimerisation in suitable non-hindered cases.
• Esterification: the same active ester acylates alcohols to give esters; added magnesium chloride is often used to broaden the alcohol scope.
• DMTMM and triazinylammonium salts: reaction with N-methylmorpholine gives DMTMM, the pre-formed water- and protic-solvent-compatible coupling salt; other tertiary amines give the corresponding 2-(4,6-dimethoxytriazinyl)trialkylammonium reagents.
• Enantiodifferentiating coupling: with selected chiral tertiary amines, CDMT forms chiral triazinylammonium species used for enantiodifferentiating coupling of racemic N-protected amino acids.
• Carboxylic-acid reduction: beyond acylation, CDMT activates carboxylic acids for reduction to the corresponding aldehydes or alcohols via the triazine active ester.

Further Reading

For guidance on selecting between carbodiimides, aminium/uronium salts, phosphonium salts and other reagent classes for amide and peptide bond formation, see NorrChemica's Lab Journal guide: Choosing a Coupling Reagent for Amide and Peptide Bond Formation.