:Scandium(III) trifluoromethanesulfonate

{{short description|Chemical compound}}

{{Chembox

| verifiedrevid = 472265558

| ImageFile1=scandium triflate.png

| ImageFile2=Scandium-triflate-hydrate-xtal-293K-3D-SF.png

| IUPACName=Scandium trifluoromethanesulfonate

| OtherNames=

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=144026-79-9

| PubChem = 2734571

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2016319

| SMILES = C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].C(F)(F)(F)S(=O)(=O)[O-].[Sc+3]

| InChI = 1/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

| InChIKey = HZXJVDYQRYYYOR-DFZHHIFOAT

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = HZXJVDYQRYYYOR-UHFFFAOYSA-K

}}

|Section2={{Chembox Properties

| Formula=C₃F₉O₉S₃Sc

| MolarMass=492.16 g/mol

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| ExternalSDS = [http://msds.chem.ox.ac.uk/SC/scandium_trifluoromethanesulfonate.html Oxford MSDS]

| FlashPt=

| AutoignitionPt =

}}

}}

Scandium trifluoromethanesulfonate, commonly called scandium triflate, is a chemical compound with formula Sc(SO₃CF₃)₃, a salt consisting of scandium cations Sc³⁺ and triflate {{chem|SO|3|CF|3|−}} anions.

Scandium triflate is used as a reagent in organic chemistry as a Lewis acid.{{cite journal |doi =10.1055/s-1999-5997 |title= SYNLETT Spotlight 12: Scandium Triflate |author= Deborah Longbottom |journal= Synlett |year= 1999 |issue= 12 |pages= 2023 |volume =1999|doi-access= free }} Compared to other Lewis acids, this reagent is stable towards water and can often be used in organic reactions as a true catalyst rather than one used in stoichiometric amounts. The compound is prepared by reaction of scandium oxide with trifluoromethanesulfonic acid.

An example of the scientific use of scandium triflate is the Mukaiyama aldol addition reaction between benzaldehyde and the silyl enol ether of cyclohexanone with an 81% yield.{{cite journal |journal= Eur. J. Org. Chem. |title= Scandium Triflate in Organic Synthesis |author= S. Kobayashi |volume= 1999 |year= 1999 |pages= 15–27 |url= http://www3.interscience.wiley.com/journal/10049248/abstract |archive-url= https://archive.today/20130105214053/http://www3.interscience.wiley.com/journal/10049248/abstract |url-status= dead |archive-date= 2013-01-05 |doi= 10.1002/(SICI)1099-0690(199901)1999:1<15::AID-EJOC15>3.0.CO;2-B|url-access= subscription }}

:File:ScOTf3-mediated aldol condensation transp.png{{clear-left}}