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Cerium(III) chloride heptahydrate is used in the preparation of allylsilanes from esters. It is used as a reducing agent in organic synthesis in place of sodium borohydride. In Luche reaction, carvone gives selectively allylic alcohol.
Reagent for selective cleavage of MEM ethers (see 2-Methoxyethoxymethyl chloride, L01050 ) under mild conditions: Org. Lett., 3, 1149 (2001).
Useful in modifying the reactivity of Sodium borohydride, 35788 , allowing selective reduction of ketones in the presence of aldehydes: J. Am. Chem. Soc., 101, 5848 (1979), and giving increased selectivity for 1,2-reduction of enones to allylic alcohols: J. Chem. Soc., Chem. Commun., 601 (1978); cyclohexenones can be reduced in an alkyl alcohol to give the alkyl allylic ether in high yield: Pol. J. Chem., 69, 1655 (1995).
With a catalytic amount of NaI in acetonitrile, dioxolanes (ethylene acetals) are deprotected to the parent carbonyl compounds: J. Org. Chem., 62, 4183 (1997), as are 4-methoxybenzyl ethers: J. Org. Chem., 64, 5696 (1999), and allyl ethers: Tetrahedron Lett., 40, 7293 (1999), to the parent alcohols. With a stoichiometric amount of NaI, alcohols can be converted to alkyl iodides: J. Org. Chem., 65, 2830 (2000), aryl alkyl ethers undergo dealkylation to phenols: Chem. Lett., 738 (2000), and selective deprotection of N-Boc protected tert-butyl amino acid esters can be achieved: J. Org. Chem., 66, 4430 (2001). Also deprotects the tert-butyl ethers of alcohols: Adv. Synth. Catal., 348, 905 (2006). For a review of the CeCl3•nH2O/NaI system,as an efficient, water-tolerant Lewis Acid promoter in organic synthesis, see: Synlett, 2101 (2003).
In combination with Zn in acetonitrile, promotes the Reformatsky reaction of Ethyl bromofluoroacetate, B21579 : J. Org. Chem., 67, 72 (2002).
For preparation of the anhydrous reagent and its use in combination with organolithium or Grignard reagents to suppress side reactions with carbonyl compounds, see: Org. Synth., 76, 228 (1998).
For a brief feature on uses of this reagent, see: Synlett, 1935 (2002).
Li, B.; Shao, X.; Hao, Y.; Zhao, Y. Ultrasonic-spray-assisted synthesis of metal oxide hollow/mesoporous microspheres for catalytic CO oxidation. RSC Adv. 2015, 5 (104), 85640-85645.
Ogata, T.; Narita, H.; Tanaka, M. Adsorption behavior of rare earth elements on silica gel modified with diglycol amic acid. Hydrometallurgy 2015, 152, 178-182.
Hazard Statements: H314
Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. 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. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant