Bismuth(III) trifluoromethanesulfonate

Base Information

• Chemical Name: Bismuth(III) trifluoromethanesulfonate
• CAS No.: 88189-03-1
• Molecular Formula: C3BiF9O9S3
• Molecular Weight: 674.2
• Hs Code.: 29049090
• European Community (EC) Number: 628-926-6
• UNII: 51KD8E1741
• DSSTox Substance ID: DTXSID70432758
• Nikkaji Number: J1.017.150D
• Mol file: 88189-03-1.mol

Synonyms:Bi(OTf)3;bismuth triflate;bismuth trifluoromethanesulfonate;bismuth(III) triflate

Chemical Property of Bismuth(III) trifluoromethanesulfonate

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.14mmHg at 25°C
• Melting Point: 300 °C
• Boiling Point: 162 °C at 760 mmHg
• PSA: 196.74000
• LogP: 3.39660
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Solubility.: Soluble in organics acetonitrile, dioxane, dimethyl formamide an
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 0
• Exact Mass: 655.83647
• Heavy Atom Count: 25
• Complexity: 145

Purity/Quality:

97% ^*data from raw suppliers

Bismuth(III)Trifluoromethanesulfonate(3:1) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical 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-].[Bi+3]
• General Description: Bismuth(III) trifluoromethanesulfonate (Bi(OTf)₃ is an efficient and environmentally friendly Lewis acid catalyst, particularly effective in promoting Friedel–Crafts alkylation reactions. It facilitates the synthesis of bis(benzofuranyl)methanes from benzofuran and aldehydes in acetonitrile, as well as the formation of 2-benzofuran-1-nitroalkanes when nitromethane is used as the solvent. The catalyst demonstrates high reactivity under mild conditions, with its performance influenced by factors such as solvent choice, temperature, and aldehyde structure. Its mechanistic role involves activating intermediates for nucleophilic attack by benzofuran, leading to high-yielding and selective transformations.

Refernces

A novel and efficient synthesis of bis(benzofuranyl)methanes and 2-benzofuran-1-nitroalkanes catalyzed by Bi(OTf)₃

10.1139/V08-091

The study investigates the synthesis of bis(benzofuranyl)methanes and 2-benzofuran-1-nitroalkanes catalyzed by Bi(OTf)3. Benzofuran and various aldehydes are the main reactants. In acetonitrile solvent, Bi(OTf)3 catalyzes the Friedel–Crafts alkylation reaction between benzofuran and aldehydes to produce bis(benzofuranyl)methanes with good yields. When nitromethane is used as the solvent, the reaction forms 2-benzofuran-1-nitroalkanes as the major products. The study explores different metal triflates as catalysts and finds Bi(OTf)3 to be particularly effective and environmentally benign. The influence of various factors such as solvent, reaction temperature, and the type of aldehyde on the reaction outcomes is examined. The proposed mechanisms for the formation of the products involve the attack of benzofuran on intermediates formed in the presence of Bi(OTf)3.