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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

Quality Level

100

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK9061
MKCH4854
MKCD1812
MKBZ1376V
MKBW7341V

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Frost, C. G.; Chauhan, K. K. et al.
Synlett, 1743-1743 (1999)
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.
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)
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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