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Maximum level of impurities: Insoluble in dilute sulfuric acid 0.05%, Cl 0.01%, PO4 0.02%, Fe 0.005%
Analytical chemistry, as an oxidant for organic compounds, as a polymerization catalyst for olefins, and as a scavenger in the manufacture of azides. 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-H290-H302-H314-H317-H335
May intensify fire; oxidizer. May be corrosive to metals. Harmful if swallowed. Causes severe skin burns and eye damage. May cause an allergic skin reaction. May cause respiratory irritation.
Precautionary Statements: P210-P220-P221-P234-P260-P264b-P270-P271-P272-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P333+P313-P363-P370+P378q-P390-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Take any precaution to avoid mixing with combustibles. Keep only in original container. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. If skin irritation or rash occurs: Get medical advice/attention. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Absorb spillage to prevent material damage. Dispose of contents/ container to an approved waste disposal plant