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T80500

Sigma-Aldrich

Trimethylsulfoxonium iodide

98%

Synonym(s):

Iodotrimethyloxosulfur, S,S,S-Trimethylsulfoxonium iodide, Trimethyl(oxo)-λ6-sulfanylium iodide, Trimethyloxosulfonium iodide, Trimethyloxosulphonium iodide, Trimethylsulfoxonium iodide (7CI)

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About This Item

Linear Formula:
(CH3)3S(I)O
CAS Number:
1774-47-6
Molecular Weight:
220.07
Beilstein:
3595854
EC Number:
217-204-2
MDL number:
MFCD00011899
UNSPSC Code:
12352100
PubChem Substance ID:
24900499
NACRES:
NA.22

Quality Level

100

Assay

98%

mp

208-212 °C (dec.) (lit.)

SMILES string

[I-].C[S+](C)(C)=O

InChI

1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1

InChI key

BPLKQGGAXWRFOE-UHFFFAOYSA-M

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Application

Treatment with strong base yields the ylide which adds to the carbonyl group of ketones and aldehydes to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000372271
0000372272
0000372271
0000372272
0000320556

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Tetrahedron, 48, 5089-5089 (1992)
Tetrahedron, 49, 5067-5067 (1993)
Optical phonons, crystal-field transitions, and europium luminescence-excitation processes in Eu2BaCoO5: Experiment and theory.
Taboada et al.
Physical review. B, Condensed matter, 50(13), 9157-9168 (1994-10-01)
W T Ashton et al.
Journal of medicinal chemistry, 35(11), 2103-2112 (1992-05-29)
A series of transition-state analogues having heterocyclythio C-termini has been synthesized and evaluated for inhibition of human renin. Addition of mercaptoheterocycles to a chiral Boc-amino epoxide intermediate led, after several steps, to the target [(2R,3S)-3-(BocPheHis-amino)-4-cyclohexyl-2-hydroxy-1-butyl]thio derivatives. Oxidation of the thioether
The Journal of Organic Chemistry, 58, 3148-3148 (1993)

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