scandium(3+) ion tritrifluoromethanesulfonate

• ChemBase ID: 99449
• Molecular Formular: C3F9O9S3Sc
• Molecular Mass: 492.1632388
• Monoisotopic Mass: 491.81198546
• SMILES: S(=O)(=O)([O-])C(F)(F)F.S(=O)(=O)(C(F)(F)F)[O-].S(=O)(=O)(C(F)(F)F)[O-].[Sc+3]
• Canonical SMILES: FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.FC(S(=O)(=O)[O-])(F)F.[Sc+3]
• InChI: InChI=1S/3CHF3O3S.Sc/c3*2-1(3,4)8(5,6)7;/h3*(H,5,6,7);/q;;;+3/p-3
• InChIKey: HZXJVDYQRYYYOR-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: scandium(3+) ion tritrifluoromethanesulfonate
• IUPAC Traditional name: scandium(3+) ion tritriflate
• Synonyms: Scandium(III) triflate; Scandium(III) trifluoromethanesulphonate 99%; Sc(OTf)3; Scandium(III) trifluoromethanesulfonate; Trifluoromethanesulfonic acid scandium(III) salt; Scandium(III) triflate; Scandium(III) trifluoromethanesulfonate; Trifluoromethanesulfonic acid scandium salt; Scandium trifluoromethanesulfonate; Scandium(III) trifluoromethanesulfonate; PS-Sc(OTf)2; Scandium triflate resin; Scandium(III) bis(trifluoromethanesulfonate), polymer-bound; Scandium tris(trifluoromethanesulfonate); 三氟甲基磺酸钪; 三氟甲磺酸 钪(III) 盐; 三氟甲烷磺酸钪; 三氟甲磺酸 钪盐; 三氟甲磺酸钪(III); 三氟甲磺酸钪树脂; 聚合物键合型双(三氟甲烷磺酸)钪(III)

Database IDs

• CAS Number: 144026-79-9
• MDL Number: MFCD00192433; MFCD00798539
• Beilstein Number: 8510151
• PubChem SID: 24871885; 24888243; 162085714; 24866212; 24881276
• PubChem CID: 2734571
• Chemspider ID: 2016319
• Wikipedia Title: Scandium(III)_trifluoromethanesulfonate

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: true

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: >300 °C; 300°C

Safety Information

• Storage Warning: Hygroscopic; Irritant/Hygroscopic/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-36
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (KT); 98%; 99%; 99.995% trace metals basis
• Grade: purum
• Particle Size: 30-60 mesh
• Extent of Labeling: 0.5-1.5 mmol/g loading
• Linear Formula: (CF3SO3)3Sc; Sc(SO3CF3)3

DETAILS

Sigma Aldrich - 483354

Packaging
1 g in glass bottle

Sigma Aldrich - 418218

Application
Extremely active, efficient, recoverable and reusable acylation catalyst,1
Important catalyst in Friedel-Crafts acylation, Diels-Alder reactions, and other carbon-carbon bond-forming reactions. Stereochemically catalyzes the radical polymerization of acrylates.
Used with triethylsilane to reductively open functionalized pyranoside rings. Lewis acid employed in the key step of a synthesis of bullvalone via a stabilized sulfur ylide.
Packaging
1, 5 g in glass bottle
250 mg in glass bottle

Sigma Aldrich - 590312

Application
Polymer-supported catalyst.
Features and Benefits
Recyclable acylation catatlyst.1
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 84645

Other Notes
Reusable Lewis acid catalyst employed e.g. for Diels-Alder CA, aldol, Michael and other reactions1,2

REFERENCES

• Catalyst for a one-pot synthesis of diaryl sulfoxides from arenes and thionyl chloride: Synlett, 784 (2002). Catalyst for methoxymethylation of alcohols with Dimethoxymethane, A12055: Tetrahedron Lett., 44, 6051 (2003). Selective addition of allyltrimethylsilane to aldehydes can be accomplished in the presence of a ketone: Synthesis, 1822 (1998).
• Water-tolerant and potentially reusable, highly active Lewis acid catalyst. Applications include:
• O-Acylation of alcohols with acetic anhydride: J. Am. Chem. Soc., 117, 4413 (1995); Org. Synth., 77, 45 (1999), or acetic acid: Chem. Commun., 351 (1997). Aldol and Michael reactions of silyl enol ethers: Synlett, 472 (1993). Friedel-Crafts acylations: Synlett, 545 (1994); (in combination with LiClO₄): Chem. Commun., 183 (1996). Fries rearrangement: J. Chem. Soc., Chem. Commun., 1527 (1995). Hetero Diels-Alder reactions: J. Chem. Soc., Chem. Commun., 1195 (1995).
• Catalyzes the Paal-Knorr synthesis of dialkylpyrroles from 1,4-diones under extremely mild, solvent-free conditions: Tetrahedron Lett., 47, 5383 (2006).
• For reviews of applications, see: Eur. J. Org. Chem., 15 (1999); Synlett, 2023 (1999).