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16774-21-3 - Cerium(IV) ammonium nitrate, 98+% - Ammonium cerium(IV) nitrate - CAN - A12882 - Alfa Aesar

A12882 Cerium(IV) ammonium nitrate, 98+%

CAS Number
16774-21-3
Synonyms
Ammonium cerium(IV) nitrate
CAN

Size Price ($) Quantity Availability
50g 26.06
250g 79.21
1000g 257.50
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Cerium(IV) ammonium nitrate, 98+%

MDL
MFCD00151121
EINECS
240-827-6

Chemical Properties

Formula
H8CeN8O18
Formula Weight
548.23
Solubility
Soluble in water and alcohol.

Applications

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.

Notes

Store in cool place. Hygroscopic. Incompatible with strong reducing agents and powdered metals.

Literature References

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).

For formation of dithioacetals, see 1,2-Ethanedithiol, L12865. For cleavage of dithioacetals, see 1,3-Dithiane, A10505.

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H272-H315-H319-H335

May intensify fire; oxidizer. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P221-P210-P220-P261-P280-P305+P351+P338-P304+P340-P362-P405-P501a

Take any precaution to avoid mixing with combustibles. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep/Store away from clothing/combustible materials. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,1992
Hazard Class
5.1
Packing Group
II
Harmonized Tariff Code
2846.10
TSCA
Yes

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