Scandium(III) trifluoromethanesulfonate: Difference between revisions

Scandium(III) trifluoromethanesulfonate
Names
	IUPAC name Scandium trifluoromethanesulfonate
Identifiers
CAS Number	144026-79-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	2016319 ;
ECHA InfoCard	100.157.499
PubChem CID	2734571;
CompTox Dashboard (EPA)	DTXSID70370368 ;
	InChI InChI=1S/3CHF3O3S.Sc/c32-1(3,4)8(5,6)7;/h3(H,5,6,7);/q;;;+3/p-3 Key: HZXJVDYQRYYYOR-UHFFFAOYSA-K ; InChI=1/3CHF3O3S.Sc/c32-1(3,4)8(5,6)7;/h3(H,5,6,7);/q;;;+3/p-3 Key: HZXJVDYQRYYYOR-DFZHHIFOAT;
	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];
Properties
Chemical formula	C3F9O9S3Sc
Molar mass	492.16 g/mol
Hazards
Safety data sheet (SDS)	Oxford MSDS
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Browse history interactively

← Previous edit

Content deleted Content added

VisualWikitext

Inline

Latest revision as of 20:26, 16 December 2021

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

Scandium triflate is used as a reagent in organic chemistry as a Lewis acid.^[1] 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.^[2]

References

^ Deborah Longbottom (1999). "SYNLETT Spotlight 12: Scandium Triflate". Synlett. 1999 (12): 2023. doi:10.1055/s-1999-5997.
^ S. Kobayashi (1999). "Scandium Triflate in Organic Synthesis". Eur. J. Org. Chem. 1999: 15–27. doi:10.1002/(SICI)1099-0690(199901)1999:1<15::AID-EJOC15>3.0.CO;2-B. Archived from the original on 2013-01-05.

[1] Deborah Longbottom (1999). "SYNLETT Spotlight 12: Scandium Triflate". Synlett. 1999 (12): 2023. doi:10.1055/s-1999-5997.

[2] S. Kobayashi (1999). "Scandium Triflate in Organic Synthesis". Eur. J. Org. Chem. 1999: 15–27. doi:10.1002/(SICI)1099-0690(199901)1999:1<15::AID-EJOC15>3.0.CO;2-B. Archived from the original on 2013-01-05.

[1]

[2]

@@ Line 1: / Line 1: @@
+{{short description|Chemical compound}}
-{{chembox
+{{Chembox
 | verifiedrevid = 472265558
 | ImageFile1=scandium triflate.png
@@ Line 18: / Line 19: @@
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = HZXJVDYQRYYYOR-UHFFFAOYSA-K
-  }}
+}}
 |Section2={{Chembox Properties
 | Formula=C<sub>3</sub>F<sub>9</sub>O<sub>9</sub>S<sub>3</sub>Sc
@@ Line 27: / Line 28: @@
 | 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(SO<sub>3</sub>CF<sub>3</sub>)<sub>3</sub>, a [[salt (chemistry)|salt]] consisting of [[scandium]] [[cation]]s Sc<sup>3+</sup> and [[triflate]] {{chem|SO|3|CF|3|−}} [[anion]]s.
+Scandium triflate is used as a reagent in organic chemistry as a [[Lewis acid]].<ref>{{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 }}</ref> Compared to other Lewis acids, this reagent is stable towards water and can often be used in [[organic reaction]]s 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 (chemistry)|yield]].<ref>{{cite journal |journal= [[European Journal of Organic Chemistry|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}}</ref>
-'''Scandium trifluoromethanesulfonate''', commonly called '''scandium triflate''', is a [[chemical compound]] with formula Sc(SO<sub>3</sub>CF<sub>3</sub>)<sub>3</sub>, a [[salt (chemistry)|salt]] consisting of [[scandium]] [[cation]]s  Sc<sup>3+</sup> and [[triflate]] SO<sub>3</sub>CF<sub>3</sub><sup>−</sup> [[anion]]s.
+:[[File:ScOTf3-mediated aldol condensation transp.png|400px|left|Sc(OTf)<sub>3</sub>-mediated aldol condensation]]{{clear-left}}
-Scandium triflate is used as a reagent in organic chemistry as a [[Lewis acid]].<ref>{{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}}</ref> Compared to other Lewis acids, this reagent is stable towards water and can often be used in an [[organic reaction]] as a true [[catalyst]] rather than one used in stoichiometric amounts. The compound is prepared by reaction of [[scandium oxide]] with [[trifluoromethanesulfonic acid]].
+== See also ==
-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% [[chemical yield]].<ref>{{cite journal | journal = [[European Journal of Organic Chemistry|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 | doi = 10.1002/(SICI)1099-0690(199901)1999:1<15::AID-EJOC15>3.0.CO;2-B }}</ref>
+* [[Lanthanide trifluoromethanesulfonates]]
-:[[Image:ScOTf3-mediated aldol condensation transp.png|400px|left|ScOTf3-mediated aldol condensation]]{{clear-left}}
-== References ==
+==References==
-{{reflist}}
+{{Reflist}}
-{{commons category|Scandium(III) triflate}}
+{{Commons category|Scandium(III) triflate}}
+{{Scandium compounds}}
 [[Category:Scandium compounds]]
 [[Category:Triflates]]
+[[Category:Acid catalysts]]