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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)

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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)
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)
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

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