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.

N-Methylhydroxylamine
N-methylhydroxylamine
N-methylhydroxylamine
Names
Preferred IUPAC name
N-Hydroxymethanamine
Other names
Methylhydroxylamine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/CH5NO/c1-2-3/h2-3H,1H3
    Key: CPQCSJYYDADLCZ-UHFFFAOYSA-N
  • CNO
Properties
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

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.[2]

See also

References
  1. Bissot, T. C.; Parry, R. W.; Campbell, D. H. (1957). "The Physical and Chemical Properties of the Methylhydroxylamines". Journal of the American Chemical Society. 79 (4): 796–800. doi:10.1021/ja01561a005.
  2. Gan, Yongping; Zhang, Wenkui; Huang, Hui; Xia, Xinhui; Cheng, Yongsheng (2006). "Industrial Synthesis of N-Methylhydroxylamine Hydrochloride by Electrochemical Reduction of Nitromethane". Chinese Journal of Chemical Engineering. 14 (5): 649. doi:10.1016/S1004-9541(06)60129-8.


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