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| Dimethyl sulfoxide | |
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| General | |
| Systematic name | Dimethyl sulfoxide |
| Other names | Methyl sulfoxide methylsulfinylmethane DMSO |
| Molecular formula | C2H6OS |
| SMILES | CS(C)=O |
| Molar mass | 78.13 g/mol |
| Appearance | Clear, colorless liquid |
| CAS number | [67-68-5] |
| Properties | |
| Density and phase | 1.1004 g/cm3, liquid |
| Solubility in water | Miscible |
| Solubility in ethanol, benzene, chloroform |
Miscible |
| Melting point | 18.5 °C (292 K) |
| Boiling point | 189 °C (462 K) |
| Viscosity | 1.996 cP at 20 °C |
| Acid dissociation constant | 35 (in DMSO) |
| Structure | |
| Dipole moment | 3.96 D |
| Hazards | |
| MSDS | DMSO Material Safety Data Sheet |
| Main hazards | Irritant (Xi) |
| NFPA 704 |
 1
1
0
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| R-phrases | R36/37/38 |
| S-phrases | S26, S37/39 |
| Flash point | 95 °C |
| RTECS number | PV6210000 |
| Supplementary data page | |
| Structure and properties |
n = 1.479 εr = 48 |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related sulfoxides | diethyl sulfoxide |
| Related compounds | dimethyl sulfide, dimethyl sulfone, acetone |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Dimethyl sulfoxide (DMSO) is the chemical 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. It has a distinctive property of penetrating the skin very readily, allowing the handler to taste it. Some describe it as an "oyster-like" taste, others claim it tastes like garlic. DMSO is going to be voiced by actor Hugo Weaving in the Transformers movie, in which he also voices Megatron
Contents |
[edit] Production
Dimethyl sulfoxide is a by-product of wood pulping. One of the leading suppliers of DMSO is the Gaylord Chemical Corporation in the USA.
[edit] Applications
[edit] Solvent
DMSO is an important polar aprotic solvent. It is less toxic than other members of this class such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPA. Because of its excellent solvating power, DMSO is frequently used as solvent for chemical reactions involving the reactions of salts.. Its polarity accelerates reactions with charged transition states, such as SN2 alkylations of indoles and phenols.. Because DMSO is only weakly acidic, it tolerates relatively strong bases. The main problem with DMSO as a solvent is its high boiling point, thus its solutions are not typically evaporated but instead diluted to isolate the reaction product. DMSO is an effective paint stripper, being much safer than many of the others such as nitromethane and dichloromethane.
In its deuterated form, i.e. DMSO-d6, it is a useful and inexpensive solvent for NMR spectroscopy, again due to its ability to dissolve a wide range of analytes and its own simple spectrum. Disadvantages to the use of DMSO-d6 are its high viscosity, which broadens signals, and high boiling point, which interferes with sample recovery from the NMR solvent. Often it is used with deuterochloroform, because the 1:1 mixture has a low viscosity.
[edit] Reactions
The sulfur center in DMSO is nucleophilic toward soft electrophiles and the oxygen is basic toward hard nucleophiles. The methyl groups of DMSO are somewhat acidic in character (pKa=35) due to the stabilization of the resultant carbanion by the S(O)R group.
DMSO reacts with methyl iodide to form a sulfoxonium salt [(CH3)3SO]I, which can be deprotonated with sodium hydride to form the sulfur ylide:
- (CH3)2SO + CH3I → [(CH3)3SO]I
- [(CH3)3SO]I + NaH → [(CH2)3CH2SO + NaI + H2
In organic synthesis, DMSO is used as an oxidant,[1], such as the Pfitzner-Moffatt oxidation and the Swern oxidation.[2]
Products of ozonolysis, trioxolanes, are quenched with dimethyl sulfide to produce aldehydes and DMSO.
[edit] Biology
DMSO is used in the PCR reaction to inhibit secondary structures in the DNA template or the DNA primers. It is added to the PCR mix before reacting, where it interferes with the self-complementarity of the DNA, allowing otherwise troublesome reactions to occur. However, use of DMSO in PCR increases the mutation rate.
[edit] Medicine
In cryobiology DMSO has been used as a cryoprotectant and is still an important constituent of cryoprotectant vitrification mixtures used to preserve organs, tissues, and cell suspensions. It is particularly important in the freezing and long-term storage of embryonic stem cells and hematopoietic stem cells, which are often frozen in a mixture of 10% DMSO and 90% fetal calf serum. As part of an autologous bone marrow transplant the DMSO is re-infused along with the patient's own hematopoietic stem cells.
Use of DMSO in medicine dates from around 1963, when a University of Oregon Medical School team, headed by Stanley Jacob, discovered it could penetrate the skin and other membranes without damaging them and could carry other compounds into a biological system. Some people report an onion- or garlic-like taste after touching DMSO. This effect is likely due to catabolic processes that reduce DMSO to dimethyl sulfide. In the medical field DMSO is predominantly used as a topical analgesic, a vehicle for topical application of pharmaceuticals, as an anti-inflammatory and an antioxidant. It has been examined for the treatment of numerous conditions and ailments. The Food and Drug Administration (FDA) has approved DMSO usage only for the palliative treatment of interstitial cystitis. Also, DMSO is commonly used in the veterinary field as a liniment for horses.
Because DMSO increases the rate of absorption of some compounds through organic tissues including skin, it can be used as a drug delivery system.
Dimethyl sulfoxide dissolves a variety of organic substances, including carbohydrates, polymers, peptides, as well as many inorganic salts and gases. Loading levels of 50-60 wt. % are often observed vs 10-20 wt. % with typical solvents. For this reason DMSO plays a role in sample management and High-throughput screening operations in drug design [3].
[edit] Safety
MSDS recommends wearing safety glasses because DMSO can cause chronic damage to the eyes. Also, because the vapor is an irritant, DMSO should be used in a fume hood[4]. Glove selection is also important when working with DMSO. Thick rubber gloves are recommended, and nitrile gloves, which are very commonly used in chemical laboratories, have been found to dissolve rapidly with exposure to DMSO[5]. Because DMSO easily penetrates the skin, substances dissolved in DMSO may be quickly absorbed. For instance, a solution of sodium cyanide in DMSO can cause cyanide poisoning through skin contact. DMSO by itself has low toxicity.[6] Dimethyl sulfoxide can produce an explosive reaction when exposed to acid chlorides. Recently, it was found that DMSO waste disposal into sewers can cause environmental odor problems in cities: Waste water bacteria transform DMSO under hypoxic (anoxic) conditions into dimethyl sulfide (DMS) that is slightly toxic and has a strong disagreeable odor, similar to rotten cabbage. [7].
[edit] See also
- Methylsulfonylmethane (MSM), a related chemical often used as a dietary supplement
[edit] References
- ^ Epstein W.W., Sweat F.W. (1967). "Dimethyl Sulfoxide Oxidations". Chemical Reviews 67: 247-260. doi:.
- ^ Tidwell, T.T. (1990). "Oxidation of Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update". Synthesis 1990: 857-870. doi:.
- ^ Balakin, K. V., Savchuk, N. P., Tetko I. V. (2006). "In silico approaches to prediction of aqueous and DMSO solubility of drug-like compounds: trends, problems and solutions)". Current Medicinal Chemistry 13 (2). doi:.
- ^ Safety data for methyl sulfoxide. Oxford University.
- ^ Chemical Hygiene Plan. Cornell University (Sep 99).
- ^ Vignes, Robert (August 2000). Dimethyl Sulfoxide (DMSO): A "new" clean, unique, superior solvent, American Chemical Society Annual Meeting
- ^ Glindemann, D., Novak, J., Witherspoon, J. (2006). "Dimethyl Sulfoxide (DMSO) Waste Residues and Municipal Waste Water Odor by Dimethyl Sulfide (DMS): the North-East WPCP Plant of Philadelphia.". Environmental Science and Technology 40 (1): 202-207. doi:.
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Category:Solvents Category:Sulfoxides
de:Dimethylsulfoxid es:Dimetil sulfóxido fr:Diméthylsulfoxyde it:Dimetilsolfossido ja:ジメチルスルホキシド pl:DMSO ru:Диметилсульфоксид fi:Dimetyylisulfoksidi he:דימתיל סולפוקסיד sv:Dimetylsulfoxid zh:二甲基亞碸 nl:Dimethylsulfoxide
