Tin(II) trifluoromethanesulfonate

Base Information

• Chemical Name: Tin(II) trifluoromethanesulfonate
• CAS No.: 62086-04-8
• Molecular Formula: C2F6O6S2Sn
• Molecular Weight: 416.81
• Hs Code.: 29049090
• European Community (EC) Number: 629-277-1
• DSSTox Substance ID: DTXSID30380266
• Nikkaji Number: J209.039B
• Mol file: 62086-04-8.mol

Synonyms:Tin(II) trifluoromethanesulfonate;62086-04-8;Stannous trifluoromethanesulfonate;Tin(II) triflate;tin(2+);trifluoromethanesulfonate;tin(ii)trifluoromethanesulfonate;Stannous triflate;Tin (II) triflate;Tin trifluoromethanesulfonate;SCHEMBL524993;SCHEMBL524994;DTXSID30380266;RBGLVWCAGPITBS-UHFFFAOYSA-L;AMY37802;AKOS005762896;AKOS025243441;AKOS030228052;SY039166;Trifluoromethanesulfonic Acid Tin(II) Salt;CS-0085404;T1194

Chemical Property of Tin(II) trifluoromethanesulfonate

Chemical Property:

• Appearance/Colour: white to yellowish powder
• Vapor Pressure: 1.14mmHg at 25°C
• Melting Point: >=300 °C
• Boiling Point: 162 °C at 760 mmHg
• PSA: 131.16000
• LogP: 1.88360
• Storage Temp.: Refrigerator
• Sensitive.: Moisture Sensitive
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 0
• Exact Mass: 417.806252
• Heavy Atom Count: 17
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

TinDitriflate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R34:Causes burns.
• Hazard Codes: C,Xi
• Statements: 34-36/37/38
• Safety Statements: 26-36/37/39-45-37/39

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-].[Sn+2]
• General Description: Tin(II) trifluoromethanesulfonate (stannous triflate) is a versatile Lewis acid catalyst used in organic synthesis, particularly for carbon-carbon bond-forming reactions such as aldol and Michael additions. It enables the generation of reactive intermediates like tin(II) enolates and enethiolates, facilitating stereoselective transformations with moderate to high enantioselectivity when paired with chiral ligands. Its catalytic efficiency and ability to promote asymmetric reactions make it a valuable reagent in modern synthetic methodologies.

Refernces

CATALYTIC USE OF TIN(II) REAGENTS IN ORGANIC SYNTHESIS

10.1016/0040-4020(89)80028-6

The research details the development of new carbon-carbon bond forming reactions using catalytic amounts of tin(II) reagents in organic synthesis. The study focused on the aldol reaction, a fundamental carbon-carbon bond forming process, and the Michael reaction, aiming to achieve high stereoselectivity with minimal reagent usage. The researchers successfully developed a catalytic aldol reaction using tin(II) enolate, which was generated from a,b-unsaturated ketones, aldehydes, and ethylthiotrimethylsilane in the presence of catalytic tin(II) triflate sulfide. They also realized a catalytic asymmetric Michael reaction using tin(II) enethiolate and a catalytic amount of tin(III) triflate-chiral diamine complex. The chemicals central to this research include tin(II) triflate, ethylthiotrimethylsilane, benzaldehyde, methyl vinyl ketone, and chalcone, among others. The conclusions highlight the successful development of catalytic asymmetric reactions with moderate to good enantioselectivity, marking a significant advancement in modern organic synthesis.

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