Physical properties
bp 40–41 °C/10 mmHg; n20
D 1.4146.2
Uses
As bis-trimethylsilylated N-methylhydroxylamine N-Methyl-N,O-bis(trimethylsilyl)-
hydroxylamine can convert
aldehydes and ketones to N-methyl nitrones with regio- and
chemoselectivity; source of methylnitrene by pyrolysis;
source of the trimethylsilyl(methyl)aminyl radical by photolysis.
Preparation
It is obtained in 52% yield by reaction of Nmethylhydroxylamine
with chlorotrimethylsilane (2.0 equiv)
and triethylamine (3.3 equiv) in ether at 25 °C.
storage
N-Methyl-N,O-bis(trimethylsilyl)hydroxylamine is hydrolyzes readily upon exposure to moisture; stored without
decomposition for several months in a sealed bottle at -10 to -15 °C; relatively thermally stable, having t1/2
of 46.5 h at 140 °C; dec at 180-190 °C.
