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Cerium(IV) ammonium nitrate is widely utilized as an oxidant for many functional groups like alcohols, phenols and ethers as well as C-H bonds. It acts as a deprotection reagent for alcohol in organic synthesis. It is useful in the synthesis of heterocycles like quinoxaline derivatives which is used in dyes, organic semiconductors and DNA cleaving agents. It is an active component of chrome etchant, which is used in the production of photomasks and liquid crystal displays.
Versatile oxidizing agent. For reviews, see: Chem. Rev., 92, 29 (1992); J. Prakt. Chem./ Chem. Ztg., 336, 470 (1994); Synlett, 834 (1999); 3014 (2005); Acc. Chem. Res., 37, 21 (2004). Examples of oxidations with CAN:
Selective conversion of alcohols to aldehydes: J. Chem. Soc., 5777 (1965); J. Org. Chem., 32, 2349, 3865 (1967). Oxidation of benzylic methyl groups to aldehydes or acetates: J. Org. Chem., 31, 2033 (1966); 45, 3906 (1980). For selective oxidation of 2-methylpyrroles to the aldehydes, see: Tetrahedron Lett., 36, 4345 (1995). Phenols to quinones: Synthesis, 347 (1973); Liebigs Ann. Chem., 1655, 1669 (1986). Cleavage of vic-diols to ketones and ɑ-hydroxy ketones to acids: J. Org. Chem., 34, 869 (1969); Synthesis, 560 (1972). Conversion of ɑ-diketones and á-keto esters to carboxylic acids: J. Org. Chem., 71, 4516 (2006). Oxidative bisdecarboxylation of malonic acid derivatives: Tetrahedron Lett., 29, 769 (1988). Regeneration of carbonyl compounds from oximes or semicarbazones: Can. J. Chem., 47, 145 (1969); Synthesis, 347 (1973). Catalytic deprotection of Boc protected alcohols, amines and thiols: Tetrahedron Lett., 37, 2035 (1996). Debenzylation of N-benzyl tertiary amines: J. Chem. Soc., Perkin 1, 3765 (2000). Decomplexation of transition metal π-complexes: Org. Synth. Coll., 8, 460 (1993). Oxidative addition of olefins to the ɑ-position of ketones: Tetrahedron Lett., 28, 5357 (1987); Synth. Commun., 18, 1841 (1988).
Catalyst for mild, selective opening of epoxides: Tetrahedron, 47, 9861 (1991).
The direct conversion of aldehydes to nitriles in aqueous NH3, under extremely mild conditions, is mediated by CAN: Synlett, 262 (2003).
Adler, P.; Fadel, A.; Rabasso, N. Cerium(IV) ammonium nitrate mediated 5-endo-dig cyclization of α-amino allenylphosphonates to spirodienones. Chem. Commun. 2015, 51 (17), 3612-3615.
Najafpour, M. M.; Khoshkam, M.; Sedigh, D. J.; Zahraei, A.; Zareh, M. K. Self-healing for nanolayered manganese oxides in the presence of cerium(IV) ammonium nitrate: new findings. New J. Chem. 2015, 39 (4), 2547-2550.
Hazard Statements: H272-H315-H319-H335
May intensify fire; oxidizer. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P260-P201-P280a-P304+P340-P405-P501a
Do not breathe dust/fume/gas/mist/vapours/spray. Obtain special instructions before use. Wear protective gloves and eye/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.