{"title":"Cerium(III) Chloride","authors":"L. Paquette, G. Sabitha, J. Yadav","doi":"10.1002/047084289X.RC041.PUB2","DOIUrl":null,"url":null,"abstract":"[7790-86-5] (·7H2O) CeCl3 (MW 246.47) \n \nInChI = 1S/Ce.3ClH/h;3*1H/q+3;;;/p-3 \n \nInChIKey = VYLVYHXQOHJDJL-UHFFFAOYSA-K \n \n \n[18618-55-8] H14CeCl3O7 (MW 372.59) \n \nInChI = 1S/Ce.3ClH.7H2O/h;3*1H;7*1H2/q+3;;;;;;;;;;/p-3 \n \nInChIKey = KPZSTOVTJYRDIO-UHFFFAOYSA-K \n \n \n \n \n \n \n \n(mild Lewis acid capable of selective acetalization;2 organocerium reagents have increased oxo-3 and azaphilicity4 and greatly reduced basicity;5 in combination with NaBH4 is a selective 1,2-reducing agent6; commercially available lanthanide reagent which is a mild Lewis acid, water tolerant, nontoxic, easy to handle, inexpensive7; in combination with NaI its activity is increased dramatically, cerium(III) chloride/NaI supported on silica gel has been developed by Bartoli and marcantoni,8 to improve its utility in organic synthesis) \n \n \n \nAlternate Name: cerous chloride; cerium trichloride. \n \n \n \nPhysical Data: mp 848 °C; bp 1727 °C; d 3.92 g cm−3. \n \n \n \nSolubility: insol cold H2O; sol alcohol and acetone; slightly sol THF. \n \n \n \nForm Supplied in: white solid; widely available. \n \n \n \nDrying: for some applications the cerium trichloride must be strictly anhydrous. The following procedure has proven most efficacious: a one-necked base-washed flask containing the heptahydrate and a magnetic stirring bar was evacuated to 0.1 Torr and heated slowly to 140 °C over a 2 h period. At 70 and 100 °C, considerable amounts of water are given off, and these critical temperature zones should not be passed through too quickly. The magnetically stirred white solid is heated overnight at 140 °C, cooled, blanketed with nitrogen, treated with dry THF (10 mL g−1), and agitated at rt for 3 h. To guarantee the complete removal of water, t-butyllithium is added dropwise until an orange color persists. \n \n \n \nHandling, Storage, and Precautions: anhydrous CeCl3 should be used as prepared for best results. Cerium is reputed to be of low toxicity.","PeriodicalId":11669,"journal":{"name":"Encyclopedia of Reagents for Organic Synthesis","volume":"37 2 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2006-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Encyclopedia of Reagents for Organic Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1002/047084289X.RC041.PUB2","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
[7790-86-5] (·7H2O) CeCl3 (MW 246.47)
InChI = 1S/Ce.3ClH/h;3*1H/q+3;;;/p-3
InChIKey = VYLVYHXQOHJDJL-UHFFFAOYSA-K
[18618-55-8] H14CeCl3O7 (MW 372.59)
InChI = 1S/Ce.3ClH.7H2O/h;3*1H;7*1H2/q+3;;;;;;;;;;/p-3
InChIKey = KPZSTOVTJYRDIO-UHFFFAOYSA-K
(mild Lewis acid capable of selective acetalization;2 organocerium reagents have increased oxo-3 and azaphilicity4 and greatly reduced basicity;5 in combination with NaBH4 is a selective 1,2-reducing agent6; commercially available lanthanide reagent which is a mild Lewis acid, water tolerant, nontoxic, easy to handle, inexpensive7; in combination with NaI its activity is increased dramatically, cerium(III) chloride/NaI supported on silica gel has been developed by Bartoli and marcantoni,8 to improve its utility in organic synthesis)
Alternate Name: cerous chloride; cerium trichloride.
Physical Data: mp 848 °C; bp 1727 °C; d 3.92 g cm−3.
Solubility: insol cold H2O; sol alcohol and acetone; slightly sol THF.
Form Supplied in: white solid; widely available.
Drying: for some applications the cerium trichloride must be strictly anhydrous. The following procedure has proven most efficacious: a one-necked base-washed flask containing the heptahydrate and a magnetic stirring bar was evacuated to 0.1 Torr and heated slowly to 140 °C over a 2 h period. At 70 and 100 °C, considerable amounts of water are given off, and these critical temperature zones should not be passed through too quickly. The magnetically stirred white solid is heated overnight at 140 °C, cooled, blanketed with nitrogen, treated with dry THF (10 mL g−1), and agitated at rt for 3 h. To guarantee the complete removal of water, t-butyllithium is added dropwise until an orange color persists.
Handling, Storage, and Precautions: anhydrous CeCl3 should be used as prepared for best results. Cerium is reputed to be of low toxicity.