N-Methylhydroxylamine

N-Methylhydroxylamine or methylhydroxylamine is a hydroxylamine derivative with a methyl group replacing one of the hydrogens of the amino group. It is an isomer of methoxyamine and aminomethanol. It decomposes in an exothermic reaction (-63 kJ/mol) into methane and azanone unless stored as a hydrochloride salt.^[2]

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N-Methylhydroxylamine

Names
Preferred IUPAC name N-Hydroxymethanamine
Other names Methylhydroxylamine
Identifiers
CAS Number	593-77-1 (Free material) Y 4229-44-1 (hydrochloride) Y
3D model (JSmol)	Interactive image
ChemSpider	11157
PubChem CID	11647
UNII	V8920J3L6R (Free material) Y MGW04SJ1LZ (hydrochloride) Y
CompTox Dashboard (EPA)	DTXSID10208035
InChI InChI=1S/CH5NO/c1-2-3/h2-3H,1H3 Key: CPQCSJYYDADLCZ-UHFFFAOYSA-N
SMILES CNO
Properties
Chemical formula	CH5NO
Molar mass	47.057 g·mol−1
Melting point	38.5 °C (101.3 °F; 311.6 K)[1]
Boiling point	115.0 °C (239.0 °F; 388.1 K)[1]
Basicity (pKb)	8.04[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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The compound is commercially available as its hydrochloride salt. This can be produced by electrochemical reduction of nitromethane in hydrochloric acid using a copper anode and a graphite cathode.^[3]