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| | Trimethylsulfoxonium iodide Basic information |
| | Trimethylsulfoxonium iodide Chemical Properties |
| Melting point | 208-212 °C (dec.) (lit.) | | density | 1.7074 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | H2O: 50 mg/mL, clear | | form | Crystalline Powder | | color | White to light yellow | | PH | pH(50g/l, 25℃) : 4.8～6.0 | | Water Solubility | 15 g/L (20 ºC) | | Sensitive | Light Sensitive | | BRN | 3595854 | | InChI | InChI=1S/C3H9OS.HI/c1-5(2,3)4;/h1-3H3;1H/q+1;/p-1 | | InChIKey | BPLKQGGAXWRFOE-UHFFFAOYSA-M | | SMILES | [S+](=O)(C)(C)C.[I-] | | CAS DataBase Reference | 1774-47-6(CAS DataBase Reference) | | EPA Substance Registry System | Sulfoxonium, trimethyl-, iodide (1774-47-6) |
| Hazard Codes | Xn,Xi | | Risk Statements | 36/37/38-22 | | Safety Statements | 37/39-26-36-24/25 | | WGK Germany | 2 | | RTECS | WS3585000 | | F | 8 | | TSCA | TSCA listed | | HS Code | 29309070 | | Storage Class | 11 - Combustible Solids |
| | Trimethylsulfoxonium iodide Usage And Synthesis |
| Chemical Properties | WHITE TO LIGHT YELLOW CRYSTALLINE POWDER | | Uses | 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 | | Uses | Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of epoxides. | | Uses | Trimethylsulfoxonium iodide is a sulfoxonium salt. It is used to generate dimethyloxosulfonium methylide by reaction with sodium hydride. The latter compound is used as a methylene-transfer reagent, and is used to prepare epoxides. | | Synthesis | Trimethylsulfoxonium iodide is commonly prepared by a reaction of Dimethyl Sulfoxide with ≈2.5 equiv of Iodomethane. After refluxing for 24 h at 80°C, the reaction mixture is cooled, and the crude solid product is filtered and washed with acetone to give the trimethylsulfoxonium iodide. Iodomethane has to be handled in a fume hood because of its high volatility and toxicity. Excess MeI is used to ensure the completion of the reaction. | | storage | The iodide and chloride salts are hygroscopic and must be stored in a cool, dry place. They are incompatible with strong oxidizing agents and strong bases. The iodide salt is sensitive to light and needs to be protected from light as much as possible. | | References | [1] Synthesis (Germany), 2017, vol. 49, # 12, p. 2652 - 2662
[2] Patent: EP2570410, 2013, A1. Location in patent: Paragraph 0064
[3] Patent: US2013/231369, 2013, A1. Location in patent: Paragraph 0102
[4] Journal of the Chemical Society [Section] C: Organic, 1971, p. 414 - 424
[5] Tetrahedron, 1958, vol. 3, p. 317 |
| | Trimethylsulfoxonium iodide Preparation Products And Raw materials |
| Raw materials | Dimethyl sulfoxide-->Iodomethane | | Preparation Products | Styrene oxide-->1-BOC-4-HYDROXY-4-(HYDROXYMETHYL)-PIPERIDINE-->2-(1-Adamantyl)oxirane-->10-methoxy-1,6-dimethylergoline-8beta-methanol-->Methanone, [2-(4-methoxyphenyl)cyclopropyl]phenyl--->2,3-dihydro-6-Methoxy-3-Methylene-1H-Isoindol-1-one-->3-Methylnorcaran-2-one-->tetrahydro-3-(2-oxiranyl)Furan-->2-Methyl-1-(p-tolylsulfonyl)azetidine-->Spiro[2.5]octane-1-carboxylic acid, 6-cyclohexyl-, methyl ester-->Benzofuran, 7-oxiranyl- (9CI)-->7-Bromo-2,3-dihydrobenzofuran-3-ol-->Ethyl 2-phenyl-4-(2,2,2-trifluoroethyl)-4,5-dihydrooxazole-4-carboxylate-->2-Propyloxetane |
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