O-Methylisourea

HCID 75544

Notes Reactions

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Basic information

CAS: 2440-60-0
Standard SMILES: COC(=N)N
InChIKey: RMAHPRNLQIRHIJ-UHFFFAOYSA-N
Molecular formula: C2H6N2O
Average molar mass: 74.08 g/mol
Monoisotopic mass: 74.04801281

Overview

RN given refers to parent cpd

Names & identifiers

Preferred name: O-Methylisourea
IUPAC: methyl carbamimidate
English name: o-methylisourea
Molecular formula: C2H6N2O
Molecular weight: 74.08

Names & synonyms

O-Methylisourea2440-60-0O-MethylisouroniumRefChem:167261methyl carbamimidateCarbamimidic acid, methyl esterCarbamimidic acid,methyl ester (9CI)0-methylisoureaO-methyl isourea2-methyl-isoureamethylcarbamimidatemethoxy-formamidine

Show more names

o-methylisourea (abbreviate OMIU)MethoxyformamidineORTHO-METHYLISOUREAFluorouracil Impurity 16Carbamimidic acid methyl ester

urea, O-methyl-Methyl imidocarbamate #SCHEMBL64656SCHEMBL11655743DTXSID20903781O-Methylisourea methyl carbamimidateBBL009722STL141087

Database identifiers

CAS: 2440-60-0
PubChem CID: 75544
DTXSID: DTXSID20903781
Nikkaji: J25.774E

Properties

Computed structural properties

XLogP: -0.4
Topological polar surface area: 59.1 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 5
Formal charge: 0
Complexity: 42.9

Physicochemical properties

Melting point: 44 · 44-45 °C
Boiling point: 66.9 · 66.9±23.0 °C(Predicted)
Density: 1.17 · 1.17±0.1 g/cm3(Predicted)
solubility: free base readily sol most organic solvents. Salts sol water, methanol, ethanol.
pka: 1 · pK1:9.72(+1) (25°C)

Chemistry & industry

Applications

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

Preparation methods · 1 item

PreparationO-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.