Frémy's salt

Frémy's salt

Chembox new
ImageFile = Potassium-nitrosodisulfonate-2D.png ImageSize =
IUPACName = Potassium nitrosodisulfonate
OtherNames =
Section1 = Chembox Identifiers
CASNo = 14293-70-0
PubChem = 3032624
SMILES =
Section2 = Chembox Properties
Formula = (KSO3)2NO
MolarMass = 268.33 g/mol (Potassium salt)
Appearance =
Density =
MeltingPt =
BoilingPt =
Solubility =
Section3 = Chembox Hazards
MainHazards = Harmful (Xn)
RPhrases = R14 R20/21/22
SPhrases = S36
FlashPt =
Autoignition =

Frémy's salt, discovered in 1845 by Edmond Frémy (1814 - 1894), is a chemical compound and a strong oxidizing agent. The formal name is disodium nitrosodisulfonic acid or NO(SO3Na)2 but Frémy's salt refers equally well to the potassium salt potassium nitrosodisulfonate.

Properties and reactions

The nitroso compound is a persistent organic radical like TEMPO. It is especially useful in oxidations of phenols to hydroquinones in the Teuber reaction. [cite journal | first = Hans-J. | last = Teuber | coauthors = Benz, Siegfired | journal = Chem. Ber. | url = http://www3.interscience.wiley.com/cgi-bin/fulltext/112293483/PDFSTART | volume = 100 | pages = 2918–29 | title = Reaktionen mit Nitrosodisulfonat, XXXVI. Chinolin-chinone-(5.6) aus 5-Hydroxy-chinolinen | issue = 9 | year = 1967 [http://www3.interscience.wiley.com/journal/112293483/abstract?CRETRY=1&SRETRY=0 Abstract] (in German). OrgSynth | author = Teuber, Hans-J. | title = Use of dipotassium nitrosodisulfonate (Fremy's salt): 4,5-dimethyl-"o"-benzoquinone | prep = cv6p0480 | collvol = 6 | collvolpages = 480 | volume = 52 | pages = 88 | year = 1972]

Preparation

The salt can be prepared from sodium nitrite, sodium bicarbonate and sulfur dioxide to disodium hydroxylaminedisulfonate and carbon dioxide followed by one-electron oxidation by electrolysis in a basic solution. [OrgSynth | author = Wehrli, Pius A.; Pigott, Foster | title = Oxidation with the nitrosodisulfonate radical. I. Preparation and use of sodium nitrosodisulfonate: trimethyl-"p"-benzoquinone | collvol = 6 | collvolpages = 1010 | volume = 52 | pages = 83 | year = 1972 | prep = cv6p1010]

References


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