| Identification | Back Directory | [Name]
o-methylisourea | [CAS]
2440-60-0 | [Synonyms]
o-methylisourea
Methoxyformamidine
o-Methylisouronium
ORTHO-METHYLISOUREA
24285-39-0 (Sulfate)
Methyl carbamimidate
Fluorouracil Impurity 16
29427-58-5 (Monosulfate)
52328-05-9 (Sulfate[2:1])
5329-33-9 (Hydrochloride)
Carbamimidic acid methyl ester
o-methylisourea (abbreviate OMIU)
Carbamimidic acid,methyl ester (9CI) | [Molecular Formula]
C2H6N2O | [MOL File]
2440-60-0.mol | [Molecular Weight]
74.0818 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [Chemical Properties]
O-Methylisourea is a colorless crystal with a temperature of 44-45°C. It can evaporate with ethanol and ether vapors and absorb moisture and carbon dioxide from the air. | [Application]
Methyl Carbamimidate is preparation of Ph (3-methoxy-1,2,4-thiadiazol-5-yl)carbamate from O-methylisourea hydrochloride. | [Uses]
O-methylisourea can be used in the synthesis of heterocyclic compounds; it is a guanylation reagent and a selective alkylating agent. | [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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