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442151

Sigma-Aldrich

Indium(III) trifluoromethanesulfonate

Synonym(s):

In(OTf)3, In(TFA)3, Indium(III) triflate, Trifluoromethanesulfonic acid indium(III) salt, Tris(trifluoromethanesulfonato)indium

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About This Item

Linear Formula:
(CF3SO3)3In
CAS Number:
128008-30-0
Molecular Weight:
562.03
MDL number:
MFCD00144478
UNSPSC Code:
12161600
PubChem Substance ID:
24867732
NACRES:
NA.22

form

solid

reaction suitability

core: indium
reagent type: catalyst

SMILES string

[In+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F

InChI

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

InChI key

UCYRAEIHXSVXPV-UHFFFAOYSA-K

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Application

Reactant or reagent involved in:
  • Synthesis of stable indium bacteriochlorins
  • Studying basicities of phosphoryl compounds toward triflates Lewis acids
  • Preparation of decahydroquinoline-type toxins via intramolecular hetero Diels-Alder reactions

Catalyst for synthesis of benzoxazoles via cyclocondensations
Reagent used a Lewis acid catalyst in organic synthesis and as a co-catalyst in catalysis.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yadav, J. S.; Reddy, B. V. S. et al.
Tetrahedron Letters, 43, 1565-1565 (2002)
Trost, B. M.; Portnoy, M.; Kurihara, H.
Journal of the American Chemical Society, 118, 836-836 (1997)
Guillaume Compain et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 18(6), 683-691 (2017-01-18)
Metal triflates, often called Lewis superacids, are potent catalysts for organic synthesis. However, the reactivity of a given Lewis superacid toward a given base is difficult to anticipate. A systematic screening of catalysts is often necessary when developing synthetic methodologies.
Frost, C. G.; Chauhan, K. K. et al.
Synlett, 1743-1743 (1999)
Teruhisa Tsuchimoto et al.
Chemical communications (Cambridge, England), (7), 852-853 (2003-05-13)
A palladium-indium triflate catalyst was found to be much more active for the dimerization of vinylarenes compared with generally used cationic palladium(II) catalysts.
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