Methanesulfenylchloride
Methanesulfenyl chloride · Methylthio chloride · Methylsulfur monochloride · Methanesulfenic acid chloride · Methanesulfenyl chloride (6CI,7CI,8CI,9CI)
Identifikatoren & physikalische Daten
| CAS No. | 5813-48-9 |
|---|---|
| Summenformel | CH3ClS |
| Durchschnittliche Molmasse | 82,55 g/mol |
| Monoisotopische Masse | 81,96439878 g/mol |
| SMILES | CSCl |
| InChIKey | DDCYYCUMAFYDDU-UHFFFAOYSA-N |
| PubChem CID | 138595 |
| DTXSID | DTXSID80206846 |
Chemische & physikalische Eigenschaften
| XLogP | 1,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 25,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 3 |
| Formalladung | 0 |
| Komplexität | 4,8 |
| SpringerMaterials Properties | Schoenflies notation |
| Siedepunkt | 27-28 °C(Press: 53-60 Torr) |
| Dichte | 1.172±0.06 g/cm3(Predicted) |
| Löslichkeit | sol ether, THF, dichloromethane, chloroform, carbon tetrachloride, dimethoxyethane |
Anwendungen & Verwendung
Verwenden
Methanesulfenic acid chloride reacts as a pseudohalogen; reacts with carbanions and enolates to add the thiomethyl group α to the carbonyl; adds across the double bonds of alkenes and allenes; adds across triple bond of alkynes.
Herstellung & Synthese
synthetische
To a flask containing 23.6 gm (0.25 mole) of dimethyl disulfide at - 1 5 ° to -20°C is slowly added dropwise 34 gm (0.25 mole) of freshly distilled sulfuryl chloride while keeping the temperature at -15° to -20°C. The reaction mixture is stirred for 1 hr, and then distilled to afford 37.1 gm (90%), b.p. 27-28°C (53-60 mm Hg); NMR, 2.91 ppm (singlet). The crude product can also be used without distillation since most of the material is product.