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213136

Sigma-Aldrich

Hydroxylamine-O-sulfonic acid

97%

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About This Item

Fórmula lineal:
H2NOSO3H
Número de CAS:
2950-43-8
Peso molecular:
113.09
EC Number:
220-971-6
MDL number:
MFCD00011604
UNSPSC Code:
12352300
PubChem Substance ID:
57647921
NACRES:
NA.21

Quality Level

200

assay

97%

mp

210 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

NOS(O)(=O)=O

InChI

1S/H3NO4S/c1-5-6(2,3)4/h1H2,(H,2,3,4)

InChI key

DQPBABKTKYNPMH-UHFFFAOYSA-N

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General description

Hydroxylamine-O-sulfonic acid is a versatile synthetic reagent. It is widely employed as a nucleophile and as an electrophile in various organic syntheses. It can be synthesized by reacting hydroxylamine sulfate with 30% fuming H2SO4.

Application

Hydroxylamine-O-sulfonic acid (HOSA) may be employed in the preparation of the following:
  • monosubstituted and 1,1-disubstituted hydrazines
  • symmetrically substituted pyrroles
  • aniline
  • C-substituted amino derivatives
  • lactams
Hydroxylamine-O-sulfonic acid may be used in the following processes:
As a nitrogen transfer reagent for the conversion of aldehydes to nitriles in aqueous medium.
Synthesis of N-aminopiperidine (NAPP) by reacting with piperidine.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
STBL2883
STBL1999
STBK7420
STBK6555
STBK4932

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A New Strategy for the Preparation of N-Aminopiperidine Using Hydroxylamine-O-Sulfonic Acid: Synthesis, Kinetic Modelling, Phase Equilibria, Extraction and Processes."
Labarthe E, et al.
Advances in Chemical Engineering and Science, 3(2) (2013)
Direct synthesis of nitriles from aldehydes with hydroxylamine-O-sulfonic acid in acidic water.
Quinn DJ, et al.
Tetrahedron Letters, 57(34), 3844-3847 (2016)
Synthetic Methods and Reactions; 671. One-Step Conversion of Alicyclic Ketones into Lactams with Hydroxylamine-O-sulfonic Acid/Formic Acid.
Olah GA and Fung AP.
Synthesis, 07, 537-538 (1979)
Hydroxylamine-O-sulfonic Acid.
Erdik E and Saczewski J.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2013)
K Kohda et al.
Nucleic acids symposium series, (17)(17), 145-148 (1986-01-01)
Amination of guanosine (Guo) with 2,4-dinitrophenoxyamine in aqueous DMF gave 7-amino-Guo, which was readily converted to 8,5'-O-cyclo-Guo, and 8-hydroxy-Guo. Deoxyguanosine (dG) gave only deglycosylated 7-amino-G under the same reaction condition. Aminations of Guo and dG with hydroxylamine-O-sulfonic acid above pH
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