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Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH 3) 2 S O.This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water.
Phase behavior Triple point: 291.67 K (18.52 °C), ? Pa Critical point [2]: 720 K (447 °C), 5630 kPa Std enthalpy change of fusion, Δ fus H o: 14.37 kJ/mol Std entropy change
Deuterated DMSO, also known as dimethyl sulfoxide-d 6, is an isotopologue of dimethyl sulfoxide (DMSO, (CH 3) 2 S=O)) with chemical formula ((CD 3) 2 S=O) in which the hydrogen atoms ("H") are replaced with their isotope deuterium ("D"). Deuterated DMSO is a common solvent used in NMR spectroscopy.
The most common sulfoxide ligand is dimethyl sulfoxide (dmso). Many sulfoxides are known because an enormous range of organic substituents are possible. When the two substituents differ, the ligand is chiral. Chiral sulfoxides are configurationally stable. One example is methyl phenyl sulfoxide.
For example, dimethyl sulfide is oxidized to dimethyl sulfoxide and then further to dimethyl sulfone. Unsymmetrical sulfides are prochiral, thus their oxidation gives chiral sulfoxides. This process can be performed enantioselectively. [9] [10] Symmetrical sulfoxides can be formed from a diorganylzinc compound and liquid sulfur dioxide. [11]
Sodium methylsulfinylmethylide (also called NaDMSO or dimsyl sodium) is the sodium salt of the conjugate base of dimethyl sulfoxide. This unusual salt has some uses in organic chemistry as a base and nucleophile. Since the first publication in 1965 by Corey et al., [2] a number of additional uses for this reagent have been identified. [3]
The crude dimethyl sulfide product was purified by distillation and could then be used to produce DMSO. When Gaylord closed its Bogalusa plant in 2010, it changed its process technology to manufacture DMS from methanol and hydrogen sulfide gas via gas phase thioetherification. This is the dominant method used worldwide to make DMS and there are ...
In organic chemistry, the Swern oxidation, named after Daniel Swern, is a chemical reaction whereby a primary or secondary alcohol (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O) using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base, such as triethylamine.