Hydroxylamine-O-sulfonic acid

Hydroxylamine-O-sulfonic acid

  Oxygen, O
  Nitrogen, N
  Sulfur, S
  Hydrogen, H
Names
Other names
Aminosulfuric acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.019.065 Edit this at Wikidata
EC Number
  • 220-971-6
  • InChI=1S/H3NO4S/c1-5-6(2,3)4/h1H2,(H,2,3,4)
    Key: DQPBABKTKYNPMH-UHFFFAOYSA-N
  • NOS(=O)(=O)O
Properties
H3NO4S
Molar mass 113.09
Appearance white solid
Melting point 210 °C
cold water
Acidity (pKa) 1.48[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Hydroxylamine-O-sulfonic acid (HOSA) or aminosulfuric acid is the inorganic compound with molecular formula H3NO4S that is formed by the sulfonation of hydroxylamine with oleum.[2] It is a white, water-soluble and hygroscopic, solid, commonly represented by the condensed structural formula H2NOSO3H, though it actually exists as a zwitterion[3] and thus is more accurately represented as +H3NOSO3−. It is used as a reagent for the introduction of amine groups (–NH2), for the conversion of aldehydes into nitriles and alicyclic ketones into lactams (cyclic amides), and for the synthesis of variety of nitrogen-containing heterocycles.[3][4][5]

  1. ^ Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 115. ISBN 0-08-029214-3. LCCN 82-16524.
  2. ^ Cite error: The named reference LabPrep was invoked but never defined (see the help page).
  3. ^ a b Wiberg, Egon; Wiberg, Nils (2001). "Sulfur Compounds of Nitrogen". Inorganic Chemistry. Academic Press. pp. 675–677. ISBN 978-0-12-352651-9.
  4. ^ Wallace, Raymond G. (1980). "Hydroxylamine-O-sulfonic acid – a versatile synthetic reagent". Aldrichimica Acta. 13 (1): 3–11.
  5. ^ Rademacher, P. (2014). "Product Class 7: Hydrazines and Hydrazinium Salts (40.7.1.1.9.2 – Using Hydroxylamine-O-sulfonic Acids". In Enders, Dieter; Schaumann, E. (eds.). Compounds with One Saturated Carbon–Heteroatom Bond: Amine N-Oxides, Haloamines, Hydroxylamines and Sulfur Analogues, and Hydrazines. Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. Vol. 40b. Georg Thieme Verlag. p. 1171. ISBN 978-3-13-172181-5.