2,4-Dihydro-5-methoxy-4-methyl-3H-1,2,4-triazol-3-one Chemical Properties

Melting point:

138 - 140°C

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly, Sonicated), Methanol (Slightly), Water (Slightly, Sonicated)

form 

Solid

pka

6.85±0.20(Predicted)

color 

White to Off-White

InChI

InChI=1S/C4H7N3O2/c1-7-3(8)5-6-4(7)9-2/h1-2H3,(H,5,8)

InChIKey

AMHDHUVBOKXALL-UHFFFAOYSA-N

SMILES

N1=C(OC)N(C)C(=O)N1

LogP

-0.6--0.5 at 24-25℃ and pH5-9

Dissociation constant

10.4 at 25℃

EPA Substance Registry System

3H-1,2,4-Triazol-3-one, 2,4-dihydro-5-methoxy-4-methyl- (135302-13-5)

Safety Information

HS Code 

2933998090

2,4-Dihydro-5-methoxy-4-methyl-3H-1,2,4-triazol-3-one Usage And Synthesis

Uses

2,4-Dihydro-5-methoxy-4-methyl-3H-1,2,4-triazol-3-one is a white powder and is mainly used as a pesticide intermediate.

Uses

is used in process for the preparation of herbicide Thiencarbazone-Me in the presence of substituted Imidazole.

Synthesis

Example 7 Preparation of 5-methoxy-4-methyl-2,4-dihydro-1,2,4-triazol-3-one: 4.77 g (25.0 mmol) of methyl N'-dimethoxymethylidenehydrazine carboxylate (85% purity) was mixed with 15.3 g of 51% methanol solution of methylamine (containing 250 mmol of methylamine), and stirred at room temperature for 3 days. After completion of the reaction, the orange-red solution was concentrated under reduced pressure to remove excess methylamine to give the crude product methyl N'-(methoxymethylaminomethylene) hydrazine carboxylate. The crude product was dissolved in 15 ml of methanol, 4.95 g (27.5 mmol) of a methanolic solution of 30% sodium methanolate was added, and the reaction was heated to 50 °C for 3 h 50 min. After the reaction mixture was cooled to room temperature, it was neutralized with 2N HCl and concentrated under reduced pressure. The residue was dissolved in 6 ml of water and placed in a refrigerator overnight for crystallization. Colorless crystals were collected by filtration, washed with cold water and dried under reduced pressure to give 1.70 g (52.7% yield) of 5-methoxy-4-methyl-2,4-dihydro-1,2,4-triazol-3-one as a colorless solid with a melting point of 146-148 °C.

References

[1] Patent: US6248900, 2001, B1
[2] Patent: US6248900, 2001, B1

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