Difference between revisions of "Dimethyl sulfoxide"
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Gentle oxidation of DMSO gives dimethyl sulfone (methylsulfonylmethane). | Gentle oxidation of DMSO gives dimethyl sulfone (methylsulfonylmethane). | ||
| − | DMSO does not react with many aggressive compounds, such as [[sodium hydroxide]] or [[sodium cyanide]], even under a 24 hour reflux. Strong acids, like conc. [[sulfuric acid]] and [[hydrochloric | + | DMSO does not react with many aggressive compounds, such as [[sodium hydroxide]] or [[sodium cyanide]], even under a 24 hour reflux. Strong acids, like conc. [[sulfuric acid]] and [[hydrochloric acid]]s do not cause appreciable degradation, even at 100 °C, however, [[phosphoric acid]] will decompose DMSO at the same temperature much faster than the latter two acids.<ref>http://chemistry-chemists.com/N3_2011/U/DMSO-technical_bulletin.pdf</ref> |
DMSO will form trimethylsulfoxonium iodide with [[methyl iodide]]: | DMSO will form trimethylsulfoxonium iodide with [[methyl iodide]]: | ||
Revision as of 11:02, 17 June 2017
| Names | |
|---|---|
| IUPAC name
Dimethyl sulfoxide
| |
| Other names
Dimethyl(oxido)sulfur
DMSO Methanesulfinylmethane Methyl sulfoxide Methylsulfinylmethane | |
| Properties | |
| (CH3)2SO | |
| Molar mass | 78.13 g/mol |
| Appearance | Colorless liquid |
| Odor | Odorless (pure) Foul (technical-grade) |
| Density | 1.1004 g/cm3 (20 °C) 1.0956 g/cm3 (25 °C) 1.0908 g/cm3 (30 °C) 1.0861 g/cm3 (35 °C) 1.0806 g/cm3 (40 °C) 1.0753 g/cm3 (45 °C) 1.0704 g/cm3 (50 °C) 1.0604 g/cm3 (60 °C) |
| Melting point | 19 °C (66 °F; 292 K) |
| Boiling point | 189 °C (372 °F; 462 K) |
| Miscible | |
| Solubility | Miscible with alcohols, carboxylic acids, esters Soluble in diethyl ether Immiscible with alkanes |
| Vapor pressure | 0.42 mmHg at 20 °C |
| Acidity (pKa) | 35 |
| Thermochemistry | |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 89 °C (192 °F; 362 K) |
| Related compounds | |
| Related compounds
|
Acetone Methylsulfonylmethane |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Dimethyl sulfoxide (or DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid 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.
Contents
Properties
Chemical
DMSO will oxidize a primary halide to form an aldehyde, process known as Kornblum oxidation.
Gentle oxidation of DMSO gives dimethyl sulfone (methylsulfonylmethane).
DMSO does not react with many aggressive compounds, such as sodium hydroxide or sodium cyanide, even under a 24 hour reflux. Strong acids, like conc. sulfuric acid and hydrochloric acids do not cause appreciable degradation, even at 100 °C, however, phosphoric acid will decompose DMSO at the same temperature much faster than the latter two acids.[1]
DMSO will form trimethylsulfoxonium iodide with methyl iodide:
- (CH3)2SO + CH3I → [(CH3)3SO]I
Physical
DMSO is a clear, colorless, odorless liquid at standard conditions. It is miscible with a variety of liquids, such as water, alcohol, diethyl ether. As a polar aprotic solvent, DMSO can dissolve a surprising variety of organic and inorganic compounds [2]
Availability
DMSO is available at chemical suppliers. It is also commonly available at pet stores for cleaning dogs ears. In some countries, such as the Russian Federation, DMSO is sold in drugstores (it is useful for making poultices).
Preparation
DMSO can be prepared by oxidizing dimethyl sulfide with oxygen or nitrogen dioxide.
Projects
- Organic extractions
- Chemoluminescence of the Luminol-NaOH-DMSO System
Handling
Safety
DMSO penetrates the skin very readily and has the unusual property that many individuals perceive a garlic-like taste in the mouth after contact of DMSO with the skin. DMSO isn't very toxic, but it can act as a pathway to allow any toxic substances dissolved in it straight into the blood stream.
Because DMSO easily penetrates the skin, substances dissolved in DMSO may be quickly absorbed. Glove selection is important when working with DMSO. Butyl rubber, fluoroelastomer, neoprene, or thick (15 mil) latex gloves are recommended. Nitrile gloves, which are very commonly used in chemical laboratories, may protect from brief contact but have been found to degrade rapidly with exposure to DMSO.
Storage
DMSO should be stored in closed bottles, to prevent outside contamination. As it has a high boiling point, very little solvent evaporates over time. However, due to it's high melting point (19°C), DMSO will freeze if kept in a cold place. DMSO will slowly absorb water from air, so if you want to keep it dry, it's best to keep it in sealed containers/bottles, with fresh molecular sieves.
Disposal
DMSO wastes should be mixed with another organic solvent and burned in an incinerator equipped with an afterburner and a scrubber.
References
- ↑ http://chemistry-chemists.com/N3_2011/U/DMSO-technical_bulletin.pdf
- ↑ http://www.gaylordchemical.com/uploads/images/pdfs/literature/102B_english.pdf
