Tin(II) trifluoromethanesulfonate, 97%
|UN#:||UN3288||Hazard Class:||6.1||Packing Group:||III|
|Alternate Name:||Tin(II) triflate
Pricing and Availability
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|Formula weight:||416.82||Sensitivity:||Moisture Sensitive|
Versatile mild Lewis acid catalyst.
Introduced by Mukaiyama to promote aldol-type reactions via tin enolates, either stoichiometrically: Tetrahedron, 40, 1381 (1984), or catalytically: Tetrahedron, 45, 1197 (1989). In the presence of a chiral amine, the reaction is enantioselective: Chem. Lett., 1209 (1991); J. Am. Chem. Soc., 113, 4247 (1991). For further discussion of this and other reactions of tin enolates, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 7, p. 4907.
In combination with a base (e.g. DBU), promotes the addition of 1-alkynes to carbonyl groups to give alkynols: J. Org. Chem., 56, 4091 (1991).
Can transfer an allyl group from a homoallylic alcohol to an aldehyde: J. Am. Chem. Soc., 120, 6609 (1998); 122, 1310 (2000).
Promotes glycosidation reactions, e.g. of acetobromoglucose to give, stereoselectively, ß-glucosides: Tetrahedron Lett., 26, 1713 (1985). Also used in a variety of other glycosidation reactions; see, e.g.: Tetrahedron Lett., 28, 5041 (1987); Chem. Lett., 1123 (1996); Liebigs Ann. Chem., 1623 (1996); Tetrahedron, 52, 3897 (1996); Eur. J. Org. Chem., 1423 (2000).
Catalyzes electrophilic sulfonylation of aromatic rings by sulfonyl chlorides, generally in good yields: Tetrahedron, 57, 241 (2001).
Reagent for selective deprotection of N-Boc groups: Synth. Commun., 33, 445 (2003).
|Harmonized Tariff Code:||2904.90|
GHS Hazard and Precautionary Statements
Toxic if inhaled. Harmful if swallowed. Harmful in contact with skin.
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.
Risk & Safety
|Harmful by inhalation, in contact with skin and if swallowed.|
|Keep container in a well ventilated place. Wear suitable protective clothing and gloves. This material and/or its container must be disposed of as hazardous waste.|