Sodium Methylsulfinylmethylide

[15590-23-5] C2H5NaOS (MW 100.13) InChI = 1S/C2H5OS.Na/c1-4(2)3;/h1H2,2H3; InChIKey = SNRDFPUMRHPUCQ-UHFFFAOYSA-N (strong base and nucleophile; very useful for the introduction of the methylsulfinylmethyl group1) Alternate Names: sodium dimsylate; dimsylsodium. Solubility: sol DMSO. Form Supplied in: not commercially available. Analysis of Reagent Purity: titration with formanilide using triphenylmethane as indicator.2 Preparative Method: prepared by the reaction of Sodium Hydride with Dimethyl Sulfoxide for 1 h at 70 °C. Sodium Amide may also be used as base.3 Handling, Storage, and Precautions: this reagent is not exceptionally stable over long periods of time. Modifications in preparation and storage have led to an increased shelf life.4 However, it is probably best prepared as needed and used quickly. Hydrogen is emitted during the preparation of this reagent and decomposition occurs at elevated temperatures.5 Due caution should be exercised in the preparation, particularly on a large scale. Reports have been made of explosions during the large scale preparation of this reagent or its attempted isolation.1, 6