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22249

Sigma-Aldrich

Ammonium cerium(IV) nitrate

puriss. p.a., ACS reagent, ≥98.5% (RT)

Synonym(s):

CAN, Ceric ammonium nitrate

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About This Item

Linear Formula:
Ce(NH4)2(NO3)6
CAS Number:
16774-21-3
Molecular Weight:
548.22
EC Number:
240-827-6
MDL number:
MFCD00151121
UNSPSC Code:
12352302
PubChem Substance ID:
329752291
NACRES:
NB.24

grade

ACS reagent
puriss. p.a.

Quality Level

200

Assay

≥98.5% (RT)

form

powder or crystals

reaction suitability

reagent type: oxidant

anion traces

chloride (Cl-): ≤10 mg/kg
phosphate (PO43-): ≤200 mg/kg

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤50 mg/kg
K: ≤10 mg/kg
Mg: ≤20 mg/kg
Mn: ≤5 mg/kg
Na: ≤100 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

SMILES string

N.N.[Ce+4].O[N+]([O-])=O.O[N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O

InChI

1S/Ce.2HNO3.4NO3.2H3N/c;6*2-1(3)4;;/h;2*(H,2,3,4);;;;;2*1H3/q+4;;;4*-1;;

InChI key

WIBGOERAEYJBOT-UHFFFAOYSA-N

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General description

Ammonium cerium(IV) nitrate (Cerium(IV) ammonium nitrate, CAN) is a versatile reagent for oxidative electron transfer reactions. It participates in various novel carbon-carbon bond-forming reactions involved in one-pot synthesis of dihydrofurans, tetrahydrofurans and aminotetralins. Iodine/ammonium cerium(IV) nitrate has been employed in direct α-iodination of various ketones to afford the corresponding α-iodo ketones. CAN has been reported as an powerful one-electron oxidant. It also participates in various carbon-heteroatom bond-forming reactions.

Application

Ammonium cerium(IV) nitrate (CAN) may be employed as catalyst for the oxidation of aliphatic or aromatic sulfides to the corresponding sulfoxides. CAN in polyethylene glycol has been employed as an ecofriendly catalytic medium for the green synthesis of 2,5-disubstituted 1,3,4-oxadiazoles.
Ammonium cerium(IV) nitrate may be used in the following processes:
  • As a catalyst for the condensation reaction between 1,2-diketones and 1,2-diamines to form quinoxaline derivatives in water.
  • Along with iodine for the direct α-iodination/bromination of various ketones to form the corresponding α-iodo/bromo ketones.
  • As a reoxidant during the palladium-catalyzed carbonylation of triarylstibines to form carbonylated products.
  • As an oxidant for the selective oxidation of aliphatic or aromatic sulfides to sulfoxides under mild heterogeneous conditions.
  • To catalyze the formation of aryl thiocyanates by the reaction of arenes with ammonium thiocyanate.
  • Along with potassium bromide for the bromination of alkenes to corresponding dibromides.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Met. Corr. 1 - Ox. Sol. 2 - Skin Corr. 1B - Skin Sens. 1A

Storage Class Code

5.1B - Oxidizing hazardous materials

WGK

WGK 3

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Facile palladium-catalyzed carbonylation of triarylstibines in the presence of ammonium cerium (IV) nitrate.
Cho CS, et al.
The Journal of Organic Chemistry, 60(1), 274-275 (1995)
A direct synthesis of aryl thiocyanates using cerium (IV) ammonium nitrate.
Nair V, et al.
Tetrahedron Letters, 40(6), 1195-1196 (1999)
Selective and efficient oxidation of sulfides to sulfoxides using ammonium cerium (IV) nitrate in the presence of a catalytic amount of KBr or NaBr.
Zolfigol MA, et al.
Monatshefte fur Chemie / Chemical Monthly, 139(8), 895--895- (2008)
Carbon-heteroatom bond-forming reactions mediated by cerium (IV) ammonium nitrate: An overview.
Nair V, et al.
Synlett, 14(2), 156-165 (2003)
A New. ALPHA.-Iodination of Ketones Using Iodine-Ammonium Cerium (IV) Nitrate in Alcohol or Acetic Acid.
Horiuchi CA and Kiji S.
Bulletin of the Chemical Society of Japan, 70(2), 421-426 (1997)
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