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388122

Sigma-Aldrich

Tin(II) trifluoromethanesulfonate

97%

Synonym(s):

Sn(OTf)2, Stannous trifluoromethanesulfonate, Tin(II) triflate

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About This Item

Linear Formula:
(CF3SO3)2Sn
CAS Number:
62086-04-8
Molecular Weight:
416.85
MDL number:
MFCD00191251
UNSPSC Code:
12161600
PubChem Substance ID:
24864209
NACRES:
NA.22

Assay

97%

reaction suitability

core: tin
reagent type: catalyst

mp

≥300 °C (lit.)

SMILES string

FC(F)(F)S(=O)(=O)O[SnH2]OS(=O)(=O)C(F)(F)F

InChI

1S/2CHF3O3S.Sn/c2*2-1(3,4)8(5,6)7;/h2*(H,5,6,7);/q;;+2/p-2

InChI key

RBGLVWCAGPITBS-UHFFFAOYSA-L

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Application

Mild Lewis acid used for stereoselective aldol and Michael reactions; [2,3]-Wittig and Ireland-Claisen rearrangements; Horner-Wadsworth-Emmons reactions; asymmetric [3 + 2] cycloaddition; ring opening reactions; and Friedel-Crafts Reactions

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The asymmetric [3 + 2] cycloaddition reaction of chiral alkenyl Fischer carbene complexes with imines: synthesis of optically pure 2,5-disubstituted-3-pyrrolidinones.
H Kagoshima et al.
Journal of the American Chemical Society, 123(29), 7182-7183 (2001-07-19)
Yu Chen et al.
The Journal of organic chemistry, 69(2), 426-431 (2004-01-17)
The reaction of aromatic MCPs with sulfonamides catalyzed by Lewis acids affords the corresponding ring-opened homoallylic sulfonamides in good yields and the reaction of aliphatic MCPs with sulfonamides gives the corresponding pyrrolidine derivatives under the same conditions. Through deuterium-labeling experiments
Sano, S.; Yokoyama, K. et al.
Chemical Communications (Cambridge, England), 559-559 (1997)
Oh, T.; Wrobel, Z.; Rubenstein, S. M.
Tetrahedron Letters, 32, 4647-4647 (1991)

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