o-methylisourea Chemical Properties

Melting point:

44-45 °C

Boiling point:

66.9±23.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

solubility 

free base readily sol most organic solvents. Salts sol water, methanol, ethanol.

pka

pK1:9.72(＋1) (25°C)

o-methylisourea Usage And Synthesis

Uses

O-methylisourea can be used in the synthesis of heterocyclic compounds; it is a guanylation reagent and a selective alkylating agent.

Application

Methyl Carbamimidate is preparation of Ph (3-methoxy-1,2,4-thiadiazol-5-yl)carbamate from O-methylisourea hydrochloride.

Preparation

O-methylisourea hydrochloride is prepared in 69-80% yield by adding 1.15 equiv  HCl(g) with ice cooling to cyanamide dissolved in excess anhydrous methanol. The free base is obtained  from the salt using powdered KOH in a water-ether mixture or with sodium methoxide in methanol. The  monoacetate salt can be prepared from the free base with 1 equiv of HOAc. Drying: vacuum desiccator  over P2O5.

storage

Salts are hygroscopic and should be stored in a desiccator even for  brief periods. Heating O-methylisourea to decomposition can liberate toxic fumes of NOx. Use in a fume  hood.

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