indium(3+) ion tritrifluoromethanesulfonate

• ChemBase ID: 97718
• Molecular Formular: C3F9InO9S3
• Molecular Mass: 562.0253288
• Monoisotopic Mass: 561.75995156
• SMILES: [O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[In+3]
• Canonical SMILES: FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.[In+3]
• InChI: InChI=1S/3CHF3O3S.In/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3
• InChIKey: UCYRAEIHXSVXPV-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: indium(3+) ion tritrifluoromethanesulfonate
• IUPAC Traditional name: indium(3+) ion tritriflate; indium(3+) tritriflate
• Synonyms: In(OTf)3; In(TFA)3; Indium(III) triflate; Trifluoromethanesulfonic acid indium(III) salt; Tris(trifluoromethanesulfonato)indium; Indium(III) trifluoromethanesulfonate; Indium trifluoromethanesulphonate 98%; Indium triflate; Indium(III) trifluoromethanesulfonate; 三氟甲磺酸铟; 三氟甲磺酸铟(III)

Database IDs

• CAS Number: 128008-30-0
• MDL Number: MFCD00144478
• PubChem SID: 162084281; 24867732
• PubChem CID: 2734680

CALCULATED PROPERTIES

• Acid pKa: -3.4301212
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -1.2283616
• LogD (pH = 7.4): -1.2283617
• Log P: 1.1480371
• Molar Refractivity: 15.8602 cm^3
• Polarizability: 7.460577 Å^3
• Polar Surface Area: 57.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: dec.

Safety Information

• Storage Warning: Corrosive/Hygroscopic; Hygroscopic
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: II
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36; 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H314-H318; H315-H319-H335
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95+%; 99% min
• Linear Formula: (CF3SO3)3In

DETAILS

Sigma Aldrich - 442151

Application
Reagent used a Lewis acid catalyst in organic synthesis and as a co-catalyst in catalysis.
Reactant or reagent involved in:
• Synthesis of stable indium bacteriochlorins1
• Studying basicities of phosphoryl compounds toward triflates Lewis acids2
• Preparation of decahydroquinoline-type toxins via intramolecular hetero Diels-Alder reactions3Catalyst for synthesis of benzoxazoles via cyclocondensations4
Packaging
5, 25 g in glass bottle

REFERENCES

• Effective catalyst for tetrahydropyranylation and depyranylation of alcohols: Tetrahedron Lett., 43, 7975 (2002).
• For a brief feature on uses of this reagent in synthesis, see: Synlett, 899 (2003).
• Catalyst for efficient acylation of alcohols, phenols and amines, which can be acetylated in high yield with 0.1 mol% of catalyst: Synlett, 1743 (1999).
• Also catalyzes intramolecular Diels-Alder reactions, with microwave irradiation; the catalyst is potentially reusable: Tetrahedron Lett., 41, 8639 (2000).
• Catalyzes the dehydration of aldoximes to nitriles; ketoximes undergo the Beckmann rearrangement to give amides or lactams: Indian J. Chem., 41B, 154 (2002).
• Catalyst for hetero Diels-Alder reactions, e.g. of 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L14672 with imines: Tetrahedron Lett., 40, 5621 (1999):
  
• Superior to Indium(III) chloride, L18758, for the sulfonylation of both activated and deactivated aromatic rings with arylsulfonyl chlorides: Synlett, 830 (2001).
• Mild catalyst for the formation of 1,3-dithianes from carbonyl compounds with 1,3-Propanedithiol, A15261: Tetrahedron, 58, 7897 (2002), and of 1,3-oxathiolanes with 2-Mercaptoethanol, A15890: Synlett, 1535 (2002).
• Superior to several other metal triflates in the Fridel-Crafts reaction of aromatic compounds with Methyl trifluoropyruvate, B21589: Synlett, 555 (2004).