22249

Ammonium cerium(IV) nitrate

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

• Synonym(s): CAN, Ceric ammonium nitrate
• 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

Properties

• grade: ACS reagent; puriss. p.a.
• Assay: ≥98.5% (RT)
• form: powder or crystals
• reaction suitability: reagent type: oxidant
• anion traces: chloride (Cl^-): ≤10 mg/kg; phosphate (PO₄^3-): ≤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

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 Information

• Pictograms: GHS03,GHS05,GHS07,GHS09
• Signal Word: Danger
• Hazard Statements: H272,H290,H302,H314,H317,H410
• Precautionary Statements: P210 - P260 - P273 - P280 - P303 + P361 + P353 - P305 + P351 + P338
• 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