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39603
Tin(II) trifluoromethanesulfonate, 97%

CAS: 62086-04-8 MDL: MFCD00191251  
UN#:UN3288Hazard Class:6.1Packing Group:III
Alternate Name: Tin(II) triflate
Stannous triflate

 

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Chemical Properties

Formula: Sn(CF3SO3)2  Melting point: dec.
Formula weight: 416.82  Sensitivity: Moisture Sensitive
Form: Powder 

Literature References

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).


Other References

UN#: UN3288
Harmonized Tariff Code:   2904.90

GHS Hazard and Precautionary Statements

Hazard Statements : H331-H302-H312

Toxic if inhaled. Harmful if swallowed. Harmful in contact with skin.

Precautionary Statements : P261-P280-P304+P340-P311-P405-P501A

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.

Toxic

Risk & Safety

Risk Phrases: 20/21/22
Harmful by inhalation, in contact with skin and if swallowed.
Safety Phrases: 9-36/37-60
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.
Harmful
TSCA: No