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Hydroxylamine-O-sulfonic acid is used in the synthesis of quinolones for the benzodiazepine site of GABAA receptors. It is also used as a polymerization catalyst and an amination reagent. It is involved in the preparation of diazene by reacting with an alkali. It is also used in the inhibition of polychlorinated dibenzo-p-dioxins (PCDD) as well as (polychlorinated biphenyl) PCB formation in co-combustion.
Aminating agent for nucleophiles. For a review of chemistry, see: Org. Prep. Proced. Int., 14, 265 (1982).
Primary and secondary amines are converted to hydrazines: J. Org. Chem., 14, 813 (1949); Chem. Ber., 92, 2521 (1959); pyridine to 1-aminopyridinium salts: Org. Synth. Coll., 5, 43 (1977); benzotriazole to the benzyne precursor 1-aminobenzotriazole: J. Chem. Soc., Chem. Commun., 192, 193 (1965); for preparation of the bis(aminotriazolobenzene), a precursor of "1,4-dibenzyne", see: Tetrahedron Lett., 25, 2073 (1984).
Aromatic rings can be aminated in the presence of AlCl3: J. Am. Chem. Soc., 83, 221 (1961). Reaction is more successful with certain heterocycles, N,N'-dimethyluracil giving the 5-amino-derivative almost quantitatively: Tetrahedron Lett., 2751 (1973).
Reaction with ketones results in oxime sulfates which undergo the Beckmann rearrangement to amides on heating: J. Org. Chem. USSR, 17, 2284 (1981); the conversion of cyclic ketones to lactams can conveniently be carried out as a one-step operation: Synthesis, 537 (1979); J. Org. Chem., 54, 4419 (1989); Org. Synth. Coll., 7, 254 (1988).
Aldehydes are converted directly to nitriles: Tetrahedron Lett., 3187 (1974): Helv. Chim. Acta, 59, 2786 (1976).
A one-pot synthesis of aryl or heteroaryl amines from carboxylic acids (as their chlorides) has been reported, equivalent to the Schmidt or Hofmann reactions: Synthesis, 1143 (1990).
Can also provide a source of the reducing agent diimide: Liebigs Ann. Chem., 645, 1 (1962); 721, 240 (1969). For examples of the use of diimide in the reduction of alkenes, see Hydrazine monohydrate, A14005.
With aqueous NaOH, hydrodeamination of primary amines to alkanes is possible for simple aliphatic amines, amino acids or even peptides: J. Am. Chem. Soc., 100, 341 (1978).
Abe, M.; Nakano, M.; Kosaka, A.; Miyoshi, H. Syntheses of photoreactive cardiolipins for a photoaffinity labeling study. Tetrahedron Lett. 2015, 56 (17), 2258-2261.
Yang, T.; Liu, Z.; Li, X. D. Developing diazirine-based chemical probes to identify histone modification readers and erasers. Chem. Sci. 2015, 6 (2), 1011-1017.
Gefahrenhinweise (EU): H314-H318-H317-H341
Causes severe skin burns and eye damage. Causes serious eye damage. May cause an allergic skin reaction. Suspected of causing genetic defects.
Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.