Hydroxylamine-O-sulfonic acid

Hydroxylamine-O-sulfonic acid
Identifiers


CAS Number	2950-43-8
3D model (JSmol)	Interactive image
ChemSpider	68763
ECHA InfoCard	100.019.065
EC Number	220-971-6
PubChem CID	76284
InChI InChI=1S/H3NO4S/c1-5-6(2,3)4/h1H2,(H,2,3,4) Key: DQPBABKTKYNPMH-UHFFFAOYSA-N
SMILES NOS(=O)(=O)O
Properties
Chemical formula	H₃NO₄S
Molar mass	113.09
Appearance	white solid
Melting point	210 °C
Solubility in water	cold water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hydroxylamine-O-sulfonic acid ("HOSA") is the inorganic compound with the formula HONHSO₃H. It is a white, water-soluble, hygroscopic solid. It is produced formed by the sulfonation of hydroxylamine. It is a reagent for introduction of amino groups, for the conversion of aldehydes into nitriles, alicyclic ketones into lactams and for the formation of variety of nitrogen-containing heterocycles.

According to a laboratory procedure hydroxylamine-O-sulfonic acid can be prepared by treating hydroxylamine sulfate with fuming sulfuric acid (oleum). The industrial process is similar.

The sulfonation of hydroxylamine can also be effected with chlorosulfonic acid.

Analogous to sulfamic acid (H₃N⁺SO₃⁻), HOSA exists in the solid state as a zwitterion. It is H₃N⁺OSO₃⁻), consisting of ammonia attached to a sulfate group.

HOSA reacts under basic conditions as nucleophile and under neutral and acid conditions as electrophile.

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