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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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