CAS 599-71-3, Cat. No EN300-15863
Reagent-precursor to nitroxyl group
N-Hydroxybenzenesulfonamide (Piloty's acid) is a white crystalline solid (mp 120–125 °C) soluble in ethanol, diethyl ether, ethyl acetate, acetone, and warm water, but sparingly soluble in non-polar solvents. It is a precursor to nitroxyl group (HNO)1, which is generated under mildly basic, anaerobic aqueous conditions; oxygen promotes decomposition to nitric oxide (NO). Its main application is the Angeli–Rimini aldehyde test2, forming hydroxamic acids that give colored ferric complexes. It also promotes oxidative rearrangements of chlorophosphoramidites to phosphordiamidic esters, participates in hetero-Diels–Alder reactions with high regioselectivity, and can act as a catalyst in ketalization/hydrolysis. Its reactivity is influenced by pH and oxygen levels, requiring inert storage below 8 °C.
Synonyms: Piloty's acid; benzenesulfohydroxamic acid; N-hydroxybenzenesulonamide; (hydroxyamino)phenylsulfone
Selected publication
-
N-Hydroxybenzenesulfonamide.
Shenvi, R. A. Encyclopedia of Reagents for Organic Synthesis 2010. DOI: 10.1002/047084289X.rn01124
-
Angeli-Rimini’s Reaction on Solid Support: A New Approach to Hydroxamic Acids.
Porcheddu, A.; Giacomelli, G. Journal of Organic Chemistry 2006, 71 (18), 7057–7059. DOI: 10.1021/jo061018g