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Sigma-Aldrich

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

97%

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Synonym(s):
2,4-Dimethoxy-6-chloro-1,3,5-triazine, 2,4-Dimethoxy-6-chloro-s-triazine, 2-Chloro-4,6-dimethoxy-1,3,5-triazine, 2-Chloro-4,6-dimethoxy-s-triazine, 4,6-Dimethoxy-2-chloro-s-triazine, 6-Chloro-2,4-dimethoxy-s-triazine, CDMT, Chlorodimethoxytriazine
Empirical Formula (Hill Notation):
C5H6ClN3O2
CAS Number:
3140-73-6
Molecular Weight:
175.57
Beilstein:
148988
EC Number:
221-541-0
MDL number:
MFCD00075607
PubChem Substance ID:
24863373
NACRES:
NA.22

Assay

97%

form

solid

mp

71-74 °C (lit.)

SMILES string

COc1nc(Cl)nc(OC)n1

InChI

1S/C5H6ClN3O2/c1-10-4-7-3(6)8-5(9-4)11-2/h1-2H3

InChI key

GPIQOFWTZXXOOV-UHFFFAOYSA-N

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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.

Application

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.
A stable, yet highly reactive, peptide coupling agent.

Signal Word

Danger

Hazard Statements

H314 - H317 - H411

Hazard Classifications

Aquatic Chronic 2 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Munetaka Kunishima et al.
Chemical & pharmaceutical bulletin, 61(8), 882-886 (2013-08-02)
Effect of the basic property of reactants (tertiary amine catalysts, a substrate amine, and acid neutralizers) on catalytic dehydrocondensation between a carboxylic acid and an amine by using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) was studied. The reaction yield was affected by the acid-base
2-Chloro-4, 6-dimethoxy-1, 3, 5-triazine. A new coupling reagent for peptide synthesis.
Kaminski ZJ.
Synthesis, 10, 917-920 (1987)
An improved procedure for the large scale preparation of 2-chloro-4, 6-dimethoxy-1, 3, 5-triazine.
Cronin JS, et al.
Synthetic Communications, 26(!8), 3491-3494 (1996)
Munetaka Kunishima et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 18(49), 15856-15867 (2012-10-13)
The reaction of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) with various nitrogen-containing compounds, particularly tertiary amines (tert-amines), has been studied for the preparation of 2-(4,6-dimethoxy-1,3,5-triazinyl)trialkylammonium salts [DMT-Am(s)]. DMT-Ams derived from aliphatic tert-amines exhibited activity for the dehydrocondensation between a carboxylic acid and an amine
Konrad Jastrzabek et al.
Chemistry & biodiversity, 10(5), 952-961 (2013-05-18)
Bis(4,6-dimethoxy-1,3,5-triazin-2-yl) ether (4) was prepared by treatment of 2-hydroxy-4,6-dimethoxy-1,3,5-triazine with 2-chloro-4,6-dimethoxy-1,3,5-triazine in 61% yield. Ether 4, isoelectronic with pyrocarbonates, was found capable to activate carboxylic acids in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) to yield, under mild reaction conditions, superactive triazine
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