| Identification | More | [Name]
Trimethylsulfoxonium iodide | [CAS]
1774-47-6 | [Synonyms]
RARECHEM AQ A1 0066
TMSOI
TRIMETHYLSULFOXONIUM IODIDE
TRIMETHYLSULPHOXONIUM IODIDE
sulfonium,trimethyl-,iodide,oxide
Sulfoxonium,trimethyl-,iodide
trimethyl-sulfoxoniuiodide
trimethylsulphoxoniumioidie
trimethyloxosulphonium iodide
Trimethylsulfoxonium iodate
TrimethyloxosulfoniumIodideTmsoi
TrimethylSulfoxoniumIodide(Tmsoi)
Trimethylsulfoxonium
Trimethylsulfoxonium iodide, 98+%
Trimethylsulphoxonium iodide, 98+%
S,S,S-Trimethylsulfoxonium iodide
Trimethylsulfonium iodide, oxide
trimethylsulfoxoniuim iodide | [EINECS(EC#)]
217-204-2 | [Molecular Formula]
C3H9IOS | [MDL Number]
MFCD00011899 | [Molecular Weight]
220.07 | [MOL File]
1774-47-6.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE TO LIGHT YELLOW CRYSTALLINE POWDER | [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) | [Storage Precautions]
Light sensitive | [EPA Substance Registry System]
1774-47-6(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P280a-P304+P340-P305+P351+P338-P405-P501a | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [RTECS ]
WS3585000
| [F ]
8 | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29309070 | [Storage Class]
11 - Combustible Solids |
| Raw materials And Preparation Products | Back Directory | [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 |
| Hazard Information | Back Directory | [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 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. | [Uses]
Trimethylsulfoxonium Iodide is used to synthesize methylene-transfer reagents that are used in the preparation of 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 |
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