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375217

Sigma-Aldrich

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

97%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C5H6ClN3O2
Numero CAS:
3140-73-6
Peso molecolare:
175.57
Beilstein:
148988
Numero CE:
221-541-0
Numero MDL:
MFCD00075607
Codice UNSPSC:
12352100
ID PubChem:
24863373
NACRES:
NA.22

Saggio

97%

Forma fisica

solid

Punto di fusione

71-74 °C (lit.)

Stringa SMILE

COc1nc(Cl)nc(OC)n1

InChI

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

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Descrizione generale

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.

Applicazioni

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.

Avvertenze

Danger

Indicazioni di pericolo

H314,H317,H411

Classi di pericolo

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

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

Certificati d'analisi (COA)

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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
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)
2-Chloro-4, 6-dimethoxy-1, 3, 5-triazine. A new coupling reagent for peptide synthesis.
Kaminski ZJ.
Synthesis, 10, 917-920 (1987)
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
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
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