Sodium methylsulfinylmethylide

Sodium methylsulfinylmethylide

Names
Preferred IUPAC name Sodium (methanesulfinyl)methanide
Other names sodium dimsylate, dimsylsodium, NaDMSYL
Identifiers
CAS Number	15590-23-5 Y
3D model (JSmol)	Interactive image
Abbreviations	NaDMSO
ChemSpider	8329518 Y
ECHA InfoCard
E number
PubChem CID	10154010
UNII	R6HI470Q52 Y
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C2H5OS.Na/c1-4(2)3;/h1H2,2H3;/q-1;+1 Y Key: CWXOAQXKPAENDI-UHFFFAOYSA-N Y InChI=1S/C2H5OS.Na/c1-4(2)3;/h1H2,2H3;/q-1;+1 Key: CWXOAQXKPAENDI-UHFFFAOYAA Key: CWXOAQXKPAENDI-UHFFFAOYSA-N
SMILES [Na+].O=S([CH2-])C
Properties
Chemical formula	CH3S(O)CH2Na
Molar mass	100.11 g·mol−1
Appearance	White solid, solution in DMSO is green
Solubility in water	decomposes
Solubility	Very soluble in DMSO and many polar organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	May form corrosive NaOH, May be explosive in certain circumstances.
Related compounds
Related compounds	Dimethyloxosulfonium methylide, Dimethyl sulfoxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of dimethyl sulfoxide. It has the chemical formula CH₃S(O)CH−2Na⁺. This unusual salt has some uses in organic chemistry as a base and nucleophile.

Since the first publication in 1965 by Corey et al., a number of additional uses for this reagent have been identified.

Preparation

Sodium methylsulfinylmethylide is prepared by heating sodium hydride or sodium amide in DMSO

CH₃S(O)CH₃ + NaH → CH₃S(O)CH−2Na⁺ + H₂

CH₃S(O)CH₃ + NaNH₂ → CH₃S(O)CH−2Na⁺ + NH₃

Reactions

As a base

The pK_a of DMSO is 35, which leads NaDMSO to be a powerful Brønsted base. NaDMSO is used in the generation of phosphorus and sulfur ylides. NaDMSO in DMSO is especially convenient in the generation of dimethyloxosulfonium methylide and dimethylsulfonium methylide.

Reaction with esters

NaDMSO condenses with esters (1) to form β-ketosulfoxides (2), which can be useful intermediates. Reduction of β-ketosulfoxides with aluminium amalgam gives methyl ketones (3). Reaction with alkyl halides followed by elimination gives α,β-unsaturated ketones (4). β-ketosulfoxides can also be used in the Pummerer rearrangement to introduce nucleophiles alpha to a carbonyl (5).