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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

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

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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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)
The Journal of Organic Chemistry, 58, 3148-3148 (1993)
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

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