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220930

Sigma-Aldrich

Potassium nitrosodisulfonate

Synonym(s):

Dipotassium nitrosodisulfonate, Fremy’s salt

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About This Item

Linear Formula:
(KSO3)2NO
CAS Number:
14293-70-0
Molecular Weight:
268.33
EC Number:
238-219-0
MDL number:
MFCD00010878
UNSPSC Code:
12352000
PubChem Substance ID:
24853200
NACRES:
NA.22

form

powder

reaction suitability

reagent type: oxidant

storage temp.

2-8°C

SMILES string

[K+].[K+].[O]N(S([O-])(=O)=O)S([O-])(=O)=O

InChI

1S/2K.H2NO7S2/c;;2-1(9(3,4)5)10(6,7)8/h;;(H,3,4,5)(H,6,7,8)/q2*+1;/p-2

InChI key

IHSLHAZEJBXKMN-UHFFFAOYSA-L

General description

Potassium nitrosodisulfonate is an oxidizing reagent that can be used to convert phenols, naphthols, and anilines to quinones, benzylic alcohols to aldehydes or ketones, and amino acids to α-keto acids. It can also be used for the preparation of heterocyclic quinones and oxidative aromatization.

Application

Potassium nitrosodisulfonate can be used as an oxidizing reagent for the oxidation of:
  • Aromatic amines to their corresponding quinones.
  • Hydroethidine to 2-hydroxyethidium.
  • Tyrosine to o-quinones.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H260,H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Oral - Water-react 1

Supplementary Hazards

EUH014

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

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)

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F J Hornicek et al.
Chemico-biological interactions, 55(3), 289-302 (1985-11-01)
Nitroxyldisulfonate [Fremy's salt; (KSO3)2NO.] and bisulfite (NaHSO3) have abolished periodic acid (H5IO6)-induced blastogenesis of human peripheral blood lymphocytes (HPBL), but only inhibited the blastogenic response of H5IO6-oxidized rat and mouse lymphocytes, as determined by the rates of nucleic acids synthesis
Potassium Nitrosodisulfonate
Parker K, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2001)
Oxidation of aromatic amines to quinones by iodic acid under microwave irradiation in the presence of montmorillonite K10 and silica gel
Hashemi M, et al.
Monatshefte fur Chemie / Chemical Monthly, 134, 1561-1563 (2003)
M Yoshida et al.
Bioscience, biotechnology, and biochemistry, 65(6), 1444-1446 (2001-07-27)
Bisphenol A was oxidized to monoquinone and bisquinone derivatives by Fremy's salt, a radical oxidant, though salcomine and alkali did not catalyze the oxidation by molecular oxygen. Bisphenol A, bisphenol B, and 3,4'-(1-methylethylidene)bisphenol were converted to their monoquinone derivatives in
Maria-Teresa Türke et al.
Physical chemistry chemical physics : PCCP, 14(2), 502-510 (2011-11-10)
The effectiveness of dynamic nuclear polarization (DNP) as a tool to enhance the sensitivity of liquid state NMR critically depends on the choice of the optimal polarizer molecule. In this study the performance of (15)N labelled Frémy's salt as a
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