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480975

Sigma-Aldrich

Hydroxylamine-O-sulfonic acid

99.998%

Synonym(s):

(Aminooxy)(hydroxy)sulfane dioxide, (Aminooxy)sulfonic acid, Amidoperoxymonosulfuric acid, Amidosulfonic peracid, Aminomonopersulfuric acid, Ammonia-N-oxide-O-sulfonic acid betaine, Permonosulfamic acid, Sulfoperamidic acid

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About This Item

Linear Formula:
H2NOSO3H
CAS Number:
2950-43-8
Molecular Weight:
113.09
EC Number:
220-971-6
MDL number:
MFCD00011604
UNSPSC Code:
12352100
PubChem Substance ID:
24871729
NACRES:
NA.22

Quality Level

200

Assay

99.998%

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 (HOSA), an O-substituted hydroxylamine, is a widely used aminating agent. It can behave as a nucleophile as well as an electrophile. The conversion of organoboranes obtained from hydroboration of olefins to amines using HOSA has been reported.

Application

Hydroxylamine-O-sulfonic acid (HOSA) may be used to synthesize (Z)-1H-purin-6(7H)-ylideneaminooxysulfonic acid.
HOSA may be used as an aminating reagent in the synthesis of:
  • 1-aminotetrazoles and 2-aminotetrazoles
  • N-aminopiperidine (NAPP)
  • 1H,1′ H-2,2′-biimidazole-1,1′-diamine

Signal Word

Danger

Hazard Statements

H302,H314,H410

Hazard Classifications

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG8992
BCCG6881
BCBZ5283
BCBW9443
BCBS3855V

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Hydroxylamine-O-sulfonic Acid.
Erdik E and Saczewski J.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2013)
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)
N-Trinitroethylamino functionalization of nitroimidazoles: a new strategy for high performance energetic materials.
Yin P, et al.
Journal of Material Chemistry A, 1(25), 7500-7510 (2013)
Chen Zhu et al.
Journal of the American Chemical Society, 134(44), 18253-18256 (2012-10-23)
Herein, we disclose the first metal-free synthesis of primary aromatic amines from arylboronic acids, a reaction that has eluded synthetic chemists for decades. This remarkable transformation affords structurally diverse primary arylamines in good chemical yields, including a variety of halogenated
Synthesis and molecular structure of (Z)-1H-purin-6-ylideneaminooxysulfonic acid: a possible secondary metabolite of adenine.
Saczewski J and Gdaniec M.
Heterocyclic Communications, 18(3), 109-112 (2012)
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