Theilacker, W. published the artcilePreparation of O-alkylhydroxylamines, Safety of O-Isobutylhydroxylamine hydrochloride, the publication is Angewandte Chemie (1956), 303, database is CAplus.
cf. Truitt, et al., C.A. 42, 8174a. To a dried (CaCl2) solution of 10 g. ClNH2 (I) in 500 cc. Et2O is added a solution of 6 g. Na in 250-300 cc. of the required alc. and the mixture is allowed to stand 24 hrs.; or to a solution of 6 g. Na in 250-300 cc. of dry alc. (diluted with 200 cc. dioxane if necessary) heated to 80¡ã is added with vigorous stirring over 90 min. a solution of 10 g. I in 600 cc. Et2O in a manner such as to prevent contact of the Et2O solution with the walls of the reaction flask. The Et2O is allowed to distil through a packed column during the addition, and stirring is continued 15 min. more. In each case the reaction mixture is then filtered, the filtrate distilled, HCl gas passed into the distillate to precipitate NH4Cl, the mixture filtered, the filtrate saturated with HCl, and the HCl salt separated by filtration or evaporation of the solvent. Sirupy products are dried in vacuo over P2O5 and purified by recrystallization or sublimation. The following O-alkyl hydroxylamines are reported (temperature of preparation, m.p. of HCl salt, % yield, and b.p. of the base, resp., given): Me (20¡ã, 149-50¡ã, 32, 50¡ã), Et (20¡ã, 125-6¡ã, 29, 69¡ã), Pr (20¡ã, 155-7¡ã 38, 90-1¡ã), iso-Pr (20¡ã, 94-5¡ã, 38, 79-80¡ã), Bu (20¡ã, 159-60¡ã, 46, 115¡ã), iso-Bu (20¡ã, 129-30¡ã, 37, 95-7¡ã), sec-Bu (80¡ã, 68-70¡ã, 34, 103-4¡ã), tert-Bu (80¡ã, 150¡ã, 26, 200-3¡ã), (CH2)7CH3 (80¡ã, 81-2¡ã, 26, 189-92¡ã), sec-octyl, (80¡ã, 71-2¡ã, 26, 189-92¡ã), PhCH2 (80¡ã, 225-30¡ã, 51, 212-15¡ã), and cyclohexyl (80¡ã, 175¡ã, 25, 171-2¡ã).
Angewandte Chemie published new progress about 6084-58-8. 6084-58-8 belongs to catalysis-chemistry, auxiliary class Salt,Amine,Aliphatic hydrocarbon chain, name is O-Isobutylhydroxylamine hydrochloride, and the molecular formula is C4H6N2, Safety of O-Isobutylhydroxylamine hydrochloride.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia