Organic synthesis reagents | Organic ligands: dimethyl sulfoxide_industrial additives

[English name] Dimethyl sulfoxide

[Molecular formula] C2H6OS

【Molecular weight】 78.13

[CAS registration number] [67-68-5]

[Abbreviation and alias] DMSO

[Physical properties] Colorless liquid, mp 18.5 ^oC, bp 189 ^oC, 1.104 g /cm³. It is an important polar aprotic solvent. Miscible with many organic solvents and water.

【Preparation and Products】Sold by domestic and foreign chemical reagent companies. It is generally produced by oxidation of dimethyl sulfide. Due to the different oxidants and oxidation methods used, there are different production processes.

【Notes】 This reagent has strong water absorption and needs to be dried before use. At the same time, DMSO is also a weak oxidant and is non-corrosive to metals when it does not contain water; it is corrosive to iron, copper and other metals when it contains water, but does not corrode aluminum; it is stable to alkali. Heating in the presence of acid produces small amounts of compounds such as methyl mercaptan, formaldehyde, dimethyl sulfide and methanesulfonic acid. It has decomposition phenomenon at high temperatures, reacts violently with chlorine, and burns in the air with a light blue flame. This reagent should be sealed and stored in a cool, dry place away from light.

Organic synthesis reagents | Organic ligands: dimethyl sulfoxide various reactions

Dimethyl sulfoxide (DMSO) is an extremely important aprotic polar solvent that is soluble in both water and organic solvents. It is widely used as solvent and reaction reagent and has high selective extraction ability. Due to the presence of sulfur-oxygen double bonds in its structure, its molecules are very polar and can be used as ligands to coordinate with metals.

The interaction between DMSO and metal rhodium (I) can produce a complex in which three DMSO molecules are coordinated on rhodium (I) (formula 1).

The interaction between DMSO and metal platinum (II) can produce a complex in which two DMSO molecules are coordinated on platinum (II) (formula 2).

The interaction of DMSO and sodium cyanide with metallic iron (II) can produce a complex of two DMSO molecules and four cyanide ions coordinated on iron (II) Object (Formula 3).

In addition to being a ligand for coordination reactions, DMSO can also react with reducing agents to generate dimethyl sulfide because its structure contains carbon-sulfur double bonds. Ether (Formula 4).

The electronegativity of the sulfur atom in the DMSO molecule is smaller than that of the oxygen atom, making it vulnerable to attack by nucleophiles. Its reaction with amine compounds can generate S=N double bonds (Formula 5).

DMSO can react with iodobenzene in the presence of oxygen and other oxidants to generate aryl sulfone compounds (Formula 6).

DMSO can be used as a sulfur source to react with aryl iodide compounds in the presence of zinc fluoride (II) and copper bromide (I) to generate methyl aryl iodide. Based thioether (Formula 7).