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22249 Sigma-Aldrich

Ammonium cerium(IV) nitrate

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

Synonym: CAN, Ceric ammonium nitrate

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Properties

Related Categories A-B, Puriss p.a. ACS, Analytical Reagents, Analytical Reagents for General Use, Analytical/Chromatography, Cerium Salts,
Quality Level   200
grade   ACS reagent
InChI Key   WIBGOERAEYJBOT-UHFFFAOYSA-N
grade   puriss. p.a.
assay   ≥98.5% (RT)
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: ≤10 mg/kg
  Ni: ≤5 mg/kg
  Pb: ≤5 mg/kg
  Zn: ≤5 mg/kg

Description

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.

Safety & Documentation

Safety Information

Signal word 
Danger
Hazard statements 
RIDADR 
UN3085 - class 5.1 - PG 2 -EHS - acidic - Oxidizing solid, corrosive, n.o.s., HI: all
WGK Germany 
3

Documents

Certificate of Analysis (COA)

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Single- & multi-channel pipettes from BRAND
Protocols & Articles
Peer-Reviewed Papers
15

References

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