2-Chloro-4,6-dimethoxy-1,3,5-triazine

Chemical Properties

white to almost white crystalline powder

Uses

2-Chloro-4,6-dimethoxy-1,3,5-triazine may be used in the following studies:

• The specific labeling of streptavidin by the modular method for affinity labeling (MoAL).
• The preparation of bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether, via reaction with 2-hydroxy-4,6-dimethoxy-1,3,5-triazine.
• The preparation of 2-(4,6-dimethoxy-1,3,5-triazinyl)trialkylammonium salts, via reaction with various tertiary amines.
• The synthesis of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, via coupling with N-methylmorpholine in THF.

Uses

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.

General Description

2-Chloro-4,6-dimethoxy-1,3,5-triazine is a stable, yet highly reactive, peptide coupling agent. It is reported as useful coupling reagent for the purification of peptides. Catalytic amide-forming reactions of 2-chloro-4,6-dimethoxy-1,3,5-triazine has been reported. Procedure for the preparation of multikilogram quantities of 2-chloro-4,6-dimethoxy-1,3,5-triazine has been reported.

Synthesis

A preparation method of 2-chloro-4,6-dimethoxy-1,3,5-triazine comprises the following steps: using cyanuric chloride and sodium methoxide solid as reaction raw materials and N, N-dimethylformamide as a reaction solvent, gradually heating to obtain a 2-chloro-4,6-dimethoxy-1,3,5-triazine crude product, and finally, recrystallizing with heptane for purification. The reaction temperature is controlled to prepare the product, and the yield is up to 91%.