Dimethyl sulfoxide (DMSO) is a widely used solvent that is miscible with water and most organic solvents. It was first synthesized in 1866 by the Chile chemist Alexander Saytzeff, and large-scale production developed in the 20th century from dimethyl sulfide recovered in wood pulping.
Key Properties of dMSO
| Appearance | Clear, colorless liquid |
| Boiling Point | 189°C |
| Melting Point | 18.5°C |
| Density | 1.10 g/cm³ |
| Solubility | Miscible with water & organics |
| Polarity | Highly polar aprotic solvent |
| Flash Point | ~89°C |
How Is DMSO Solvent Used in Chemical Synthesis?
DMSO is a common reaction medium in organic chemistry because it dissolves a wide range of reactants, including many poorly soluble organic compounds, which improves reactant contact and conversion. Its main roles are summarized below.
| Reaction type | Role of DMSO | Example |
|---|---|---|
| SN2 substitution | Polar aprotic solvent; leaves nucleophiles more reactive | Cyanide or azide displacement of alkyl halides |
| Nucleophilic aromatic substitution (SNAr) | Stabilizes charged intermediates; allows high temperatures | Halex fluorination of aryl chlorides |
| Elimination and base-mediated reactions | Enhances base strength | Dehydrohalogenation |
| Oxidation | Oxidant (with an activator) | Swern, Parikh–Doering and Kornblum oxidations |
| Ylide chemistry | Solvent and, with strong bases, a precursor of the dimsyl anion | Corey–Chaykovsky epoxidation |
| Metal-catalyzed coupling | High-boiling polar medium | Heck and related cross-coupling reactions |
- Nucleophilic substitution, elimination and base-catalyzed reactions: as a polar aprotic solvent, DMSO solvates cations strongly but leaves anions less solvated, which raises nucleophilicity and typically speeds up SN2-type reactions.
- Oxidations: DMSO itself acts as the oxidant, with an activator (oxalyl chloride in Swern, SO₃·pyridine in Parikh–Doering), converting alcohols to aldehydes or ketones under mild conditions.
- Advanced materials: synthetic polymers, conductive materials and specialty resins.
- Electrochemistry and catalysis: battery research and electrochemical reactions, where DMSO supports ion transport and reaction stability.
- High-temperature reactions: the boiling point of about 189 °C allows high reaction temperatures and low solvent loss, which supports large-scale production.
DMSO vs Other Polar Aprotic Solvents
| Solvent | Boiling point | Melting point | Dielectric constant (approx.) |
|---|---|---|---|
| DMSO | 189 °C | 18.5 °C | 47 |
| DMF | 153 °C | −61 °C | 37 |
| DMAc | 165 °C | −20 °C | 38 |
| NMP | 202 °C | −24 °C | 32 |
| Acetonitrile | 82 °C | −45 °C | 37 |
DMSO has the highest polarity of the group and dissolves both salts and organics, but its relatively high melting point means it can solidify in cool storage. For a comparable solvent, see the solubility of dimethylacetamide (DMAc).
Dimethyl sulfoxide DMSO Solvent Organic Chemistry
Safety information
To ensure the quality and safety of DMSO chemicals:
- Store in a cool, dry, well-ventilated place.
- Keep away from strong oxidizers.
- Use airtight containers to prevent moisture absorption.
- Avoid skin contact (the substance can be absorbed through the skin).
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| Packaging Type | Net Weight |
|---|---|
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| ISO Tank | Bulk shipment |
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