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1774-47-6 molecular structure
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trimethyl(oxo)-$l^{6}-sulfanylium iodide

ChemBase ID: 85736
Molecular Formular: C3H9IOS
Molecular Mass: 220.07243
Monoisotopic Mass: 219.94188391
SMILES and InChIs

SMILES:
[I-].[S+](=O)(C)(C)C
Canonical SMILES:
C[S+](=O)(C)C.[I-]
InChI:
InChI=1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1
InChIKey:
BPLKQGGAXWRFOE-UHFFFAOYSA-M

Cite this record

CBID:85736 http://www.chembase.cn/molecule-85736.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
trimethyl(oxo)-$l^{6}-sulfanylium iodide
trimethyl(oxo)-λ6-sulfanylium iodide
IUPAC Traditional name
trimethyl(oxo)-$l^{6}-sulfanylium iodide
trimethyl(oxo)-λ6-sulfanylium iodide
Synonyms
Trimethyl(oxo)sulphonium iodide
Trimethylsulphoxonium iodide
Trimethylsulphoxonium iodide
Trimethyloxosulfonium iodide
Trimethylsulfoxonium iodide
Trimethylsulfoxonium iodide
三甲基碘化亚砜
CAS Number
1774-47-6
EC Number
217-204-2
MDL Number
MFCD00011899
Beilstein Number
3595854
PubChem SID
24900499
162072852
PubChem CID
74498
Wikipedia Title
Trimethylsulfoxonium_iodide

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) -2.5195513  LogD (pH = 7.4) -2.5195513 
Log P -2.5195513  Molar Refractivity 24.539 cm3
Polarizability 10.235904 Å3 Polar Surface Area 17.07 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
H2O: soluble50 mg/mL, clear expand Show data source
Melting Point
208-212 °C expand Show data source
208-212 °C (dec.)(lit.) expand Show data source
208-212(dec.)°C expand Show data source
ca 170°C dec. expand Show data source
Storage Warning
Irritant/Light Sensitive expand Show data source
Light Sensitive expand Show data source
RTECS
WS3585000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-37 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥97.0% (AT) expand Show data source
95+% expand Show data source
97% expand Show data source
98% expand Show data source
98+% expand Show data source
Grade
purum expand Show data source
Linear Formula
(CH3)3S(I)O expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
Sigma Aldrich - T80500 external link
Packaging
25, 100, 500 g in glass bottle
Application
Treatment with strong base yields the ylide which adds to the carbonyl group of ketones1 and aldehydes2,3 to give epoxides. Also adds preferentially to the double bond of α,β-unsaturated esters to give cyclopropyl esters.4,5
Sigma Aldrich - 92763 external link
Other Notes
Precursor of dimethylsulfoxonium methylide, a versatile C1-reagent1,2

REFERENCES

REFERENCES

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  • • Review of the chemistry of sulfonium ylides: Russ. Chem. Rev., 50, 481 (1981). Extensive review of the synthetic applications of dimethylsulfoxonium methylide: Tetrahedron, 43, 2609 (1987).
  • • For an example (conversion of cyclohexanone to the epoxide), see: Org. Synth. Coll., 5, 755 (1973). In contrast to Trimethylsulfonium iodide, A12639, reaction with ɑ?-unsaturated ketones occurs by 1,4-addition to give cyclopropanes: J. Am. Chem. Soc., 87, 1353 (1965):
  • • Reaction with epoxides gives oxetanes, unlike the sulfonium ylide which gives allylic alcohols: J. Org. Chem., 48, 5133 (1983); Synthesis, 1140 (1987); cf Tetrahedron Lett., 35, 5449 (1994):
  • • Similarly, N-arenesulfonylaziridines undergo ring expansion to azetidines with inversion at one carbon. Thus, cis-substituted aziridines give trans-azetidines and vice versa: Tetrahedron, 45, 1851 (1989):
  • • The ylide, generated with strong base, is a methylene transfer reagent.
  • • Efficient addition to enones has been effected with a highly basic system consisting of KOH in DMSO with a phase-transfer catalyst: Synth. Commun., 26, 1785 (1996).
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PATENTS

PATENTS

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INTERNET

INTERNET

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