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{{short description|Chemical compound}}
{{chembox
{{Chembox
| verifiedrevid = 472265558
| verifiedrevid = 472265558
|ImageFile1=scandium triflate.png
| ImageFile1=scandium triflate.png
⚫
| ImageFile2=Scandium-triflate-hydrate-xtal-293K-3D-SF.png
|ImageSize1=200px
⚫
| IUPACName=Scandium trifluoromethanesulfonate
⚫
|ImageFile2=Scandium-triflate-hydrate-xtal-293K-3D-SF.png
⚫
| OtherNames=
|ImageSize2=200px
⚫
|IUPACName=Scandium trifluoromethanesulfonate
⚫
|OtherNames=
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=144026-79-9
| CASNo=144026-79-9
| PubChem = 2734571
| PubChem = 2734571
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2016319
| 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]
| 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
| 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
| InChIKey = HZXJVDYQRYYYOR-DFZHHIFOAT
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| 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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HZXJVDYQRYYYOR-UHFFFAOYSA-K
| StdInChIKey = HZXJVDYQRYYYOR-UHFFFAOYSA-K
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>3</sub>F<sub>9</sub>O<sub>9</sub>S<sub>3</sub>Sc
| Formula=C<sub>3</sub>F<sub>9</sub>O<sub>9</sub>S<sub>3</sub>Sc
| MolarMass=492.16 g/mol
| MolarMass=492.16 g/mol
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| ExternalMSDS = [http://msds.chem.ox.ac.uk/SC/scandium_trifluoromethanesulfonate.html Oxford MSDS]
| ExternalSDS = [http://msds.chem.ox.ac.uk/SC/scandium_trifluoromethanesulfonate.html Oxford MSDS]
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}


'''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.
'''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}}</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]].
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 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>
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>


:[[Image:ScOTf3-mediated aldol condensation transp.png|400px|left|ScOTf3-mediated aldol condensation]]{{clear-left}}
:[[File:ScOTf3-mediated aldol condensation transp.png|400px|left|Sc(OTf)<sub>3</sub>-mediated aldol condensation]]{{clear-left}}


== References ==
== See also ==
{{reflist}}


* [[Lanthanide trifluoromethanesulfonates]]
⚫
{{commons category|Scandium(III) triflate}}

==References==
{{Reflist}}

⚫
{{Commons category|Scandium(III) triflate}}
{{Scandium compounds}}


[[Category:Scandium compounds]]
[[Category:Scandium compounds]]
[[Category:Triflates]]
[[Category:Triflates]]
[[Category:Acid catalysts]]

[[fa:تری‌فلوئورومتان‌سولفونات اسکاندیم(III)]]

Latest revision as of 20:26, 16 December 2021

Scandium(III) trifluoromethanesulfonate
Names
IUPAC name
Scandium trifluoromethanesulfonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.157.499 Edit this at Wikidata
  • InChI=1S/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3 checkY
    Key: HZXJVDYQRYYYOR-UHFFFAOYSA-K checkY
  • InChI=1/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3
    Key: HZXJVDYQRYYYOR-DFZHHIFOAT
  • 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
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).
checkY verify (what is checkY☒N ?)

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]

Sc(OTf)3-mediated aldol condensation
Sc(OTf)3-mediated aldol condensation

See also

[edit]

References

[edit]
  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.
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