Sodium Methylsulfinylmethylide
Title: Sodium Methylsulfinylmethylide
CAS Registry Number: 15590-23-5
CAS Name: Sodium sulfinylbismethane ion(1-)
Additional Names: dimsyl sodium; methylsulfinyl sodium; sodium dimethylsulfoxylate; sodium DMSO
Molecular Formula: C2H5NaOS
Molecular Weight: 100.12
Percent Composition: C 23.99%, H 5.03%, Na 22.96%, O 15.98%, S 32.03%
Literature References: Conjugate base of dimethyl sulfoxide, q.v.; nucleophilic reagent in organic chemistry. Prepn: E. J. Corey, M. Chaykovsky, J. Am. Chem. Soc. 87, 1345 (1965); of stable solns: K. Sjöberg, Tetrahedron Lett. 7, 6383 (1966). Reactivity: T. J. Broxton et al., Aust. J. Chem. 19, 521 (1966). Synthetic applications: A. J. Birch et al., ibid. 24, 2179 (1971); T. G. Warner, A. A. Benson, J. Lipid Res. 18, 548 (1977); L. Petrus et al., Carbohydr. Res. 268, 319 (1995). Brief review: M. Mondal, Synlett 2005, 2697-2698.
Properties: Highly sol in DMSO. DMSO solns are sensitive to heat and air; dec above 85°.
Use: Nucleophile in organic synthesis.

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