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About This Item
Linear Formula:
H2NOSO3H
CAS Number:
Molecular Weight:
113.09
EC Number:
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
NACRES:
NA.21
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Quality Level
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.
As a nitrogen transfer reagent for the conversion of aldehydes to nitriles in aqueous medium.
Synthesis of N-aminopiperidine (NAPP) by reacting with piperidine.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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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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)
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)
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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