Dimethyl sulfoxide
IUPAC name	Dimethyl sulfoxide
Other names	Methyl sulfoxide methylsulfinylmethane DMSO
Identifiers
CAS number	[67-68-5]
RTECS number	PV6210000
SMILES	CS(C)=O
Properties
Molecular formula	C2H6OS
Molar mass	78.13 g/mol
Appearance	Clear, colorless liquid
Density	1.1004 g/cm3, liquid
Melting point	18.5 °C (292 K) Image File history File links Download high resolution version (1100x959, 197 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Dimethyl sulfoxide ... Image File history File links Download high resolution version (1100x964, 425 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Dimethyl sulfoxide ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	189 °C (462 K) Italic text This article is about the boiling point of liquids. ...
Solubility in water	Miscible
Acidity (pKa)	35
Refractive index (nD)	1.479 εr = 48
Viscosity	1.996 cP at 20 °C
Structure
Dipole moment	3.96 D
Hazards
MSDS	External MSDS
MSDS	DMSO Material Safety Data Sheet
Main hazards	Irritant (Xi)
NFPA 704	1 1 0
R-phrases	R36/37/38
S-phrases	S26, S37/39
Flash point	95 °C
Related compounds
Related sulfoxides	diethyl sulfoxide
Related compounds	sodium methylsulfinylmethylide, dimethyl sulfide, dimethyl sulfone, acetone
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

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. Its taste has been described as oyster- or garlic-like. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... An acid dissociation constant, denoted by Ka, is an equilibrium constant for the dissociation of a weak acid. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... For other uses, see Viscosity (disambiguation). ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... This page provides supplementary chemical data on dimethyl sulfoxide. ... This page meets Wikipedias criteria for speedy deletion. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... A sulfoxide is a chemical compound containing a sulfinyl functional group with a sulfur oxygen double bond attached to two carbon atoms. ... Diethyl Sulfoxide (DESO, empirically C4H10OS), also known as Diethyl sulphoxide, ethyl sulfoxide and 1,1-Sulfinylbisethane, is a sulfur-containing organic chemical compound. ... Dimethyl sulfide causes that distinctive smell from your St. ... Methylsulfonylmethane (MSM, or dimethylsulfone) is an organic sulfur compound belonging to a class of chemicals known as sulfones. ... For other uses, see Acetone (disambiguation). ... This page provides supplementary chemical data on dimethyl sulfoxide. ... This page provides supplementary chemical data on dimethyl sulfoxide. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... This page provides supplementary chemical data on dimethyl sulfoxide. ... This page provides supplementary chemical data on dimethyl sulfoxide. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR spectroscopy) is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. ... 900MHz, 21. ... Mass spectrometry (previously called mass spectroscopy (deprecated) or informally, mass-spec and MS) is an analytical technique that measures the mass-to-charge ratio of ions. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... A chemical compound is a substance consisting of two or more different elements chemically bonded together in a fixed proportion by mass. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... In chemistry any solvent that carries hydrogen attached to oxygen as in a hydroxyl group or nitrogen as in a amine group is called a protic solvent. ... The chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ... For other uses, see Oyster (disambiguation). ... Binomial name L. Allium sativum L., commonly known as garlic, is a species in the onion family Alliaceae. ...

Production

Dimethyl sulfoxide is a by-product of wood pulping. A supplier of DMSO is the Gaylord Chemical Corporation in the USA. International Paper Company Wood pulp is the most common material used to make paper. ... Gaylord Chemical Corporation is based in the New Orleans suburb of Slidell, Louisiana. ... Motto: (traditional) In God We Trust (official, 1956–present) Anthem: The Star-Spangled Banner Capital Washington, D.C. Largest city New York City Official language(s) None at the federal level; English de facto Government Federal Republic  - President George W. Bush (R)  - Vice President Dick Cheney (R) Independence - Declared - Recognized...

Applications

Solvent

DMSO is usually not evaporated; when necessary it is distilled from the reaction mixture under high vacuum.

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 salts, most notably Finkelstein reactions and other nucleophilic substitutions. Because DMSO is only weakly acidic, it tolerates relatively strong bases, and as such has been extensively used in the study and chemistry of carbanions. The work of the Bordwell group has provided a valuable set of non-aqueous pKa values (C-H, O-H, S-H and N-H acidities) for hundreds of organic compounds in DMSO.^[1] Image File history File linksMetadata Download high-resolution version (1200x1600, 328 KB)[edit] Summary Dimethylsulfoxide usually boils at 189 °C. Under a vacuum, it distills off into the connected receiver at only 70 °C. [edit] Licensing I, the creator of this work, hereby release it into the public domain. ... Image File history File linksMetadata Download high-resolution version (1200x1600, 328 KB)[edit] Summary Dimethylsulfoxide usually boils at 189 °C. Under a vacuum, it distills off into the connected receiver at only 70 °C. [edit] Licensing I, the creator of this work, hereby release it into the public domain. ... In chemistry a protic solvent is a solvent that carries a hydrogen bond between an oxygen as in a hydroxyl group or a nitrogen as in an amine group. ... Dimethylformamide is the organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated DMF, this colourless liquid is miscible with water and majority of organic liquids. ... Dimethylacetamide (DMA or DMAc), also known as acetic acid-dimethylamide, N,N-dimethylacetamide or acetyldimethylamine, is a colorless, water miscible, high boiling, polar and hygroscopic liquid commonly used as a solvent in organic synthesis. ... N-Methyl-2-Pyrrolidone (NMP) is a keto-pyrrole, a chemical compound with 5-membered lactam structure. ... Hexamethylphosphoramide (abbreviated HMPA) is a colorless organic liquid with the formula [(CH3)2N]3PO. HMPA is the oxide of the highly basic tertiary phosphine P(NMe2)3. ... For other uses, see Solvent (disambiguation). ... The Finkelstein reaction, named for the German chemist Hans Finkelstein, is an SN2 reaction that involves the exchange of one halogen atom for another. ... In chemistry, nucleophilic substitution is a class of substitution reaction in which an electron-rich nucleophile attacks a molecule and replaces a group or atom, called the leaving group. ... A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons. ... In chemistry and biochemistry, acid dissociation constant, the acidity constant, or the acid-ionization constant () is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ...

A practical problem with DMSO as a solvent is its high boiling point, thus its solutions are not typically evaporated. Instead, reactions conducted in DMSO are often diluted with water to precipitate or phase separate organic products. DMSO is an effective paint stripper, being safer than many of the others such as nitromethane and dichloromethane. The relatively high freezing point of DMSO means that at, or just below, room temperature it is a solid, which can limit its utility in some chemical processes (e.g. crystallisation with cooling). Paint stripper, or paint remover, is the generic name given to solvent mixtures designed to removed paint and clean the underlying surface. ... Flash point 35 °C R/S statement R: S: RTECS number PA9800000 Related compounds Related nitro compounds nitroethane Related compounds methyl nitrite methyl nitrate Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references Nitromethane is an organic... R-phrases S-phrases , , Flash point None Supplementary data page Structure and properties n, εr, etc. ...

In its deuterated form, i.e. DMSO-d₆, it is a useful but expensive solvent for NMR spectroscopy, again due to its ability to dissolve a wide range of analytes, its own simple spectrum, and its suitability for high-temperature NMR spectroscopic studies. 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 lower viscosity. Deuterium, also called heavy hydrogen, is a stable isotope of hydrogen with a natural abundance in the oceans of Earth of approximately one atom in 6500 of hydrogen (~154 PPM). ... Chemical structure of deuterated DMSO Deuterated DMSO ((CD3)2S=O) is a form (called an isotopologue) of dimethyl sulfoxide (DMSO, (CH3)2S=O)) in which the hydrogen atoms (H) are replaced with deuterium (heavy hydrogen) isotope (D). Deuterated DMSO is a common solvent used in NMR spectroscopy. ... NMR redirects here. ... Deuterated chloroform (CDCl3), is a form (called a isotopologues) of chloroform (CHCl3) in which the hydrogen atom (H) is replaced with deuterium (heavy hydrogen) isotope (D). Deuterated chloroform is the most common solvent used in NMR spectroscopy. ...

Reactions

The sulfur center in DMSO is nucleophilic toward soft electrophiles and the oxygen is nucleophilic toward hard electrophiles. The methyl groups of DMSO are somewhat acidic in character (pK_a=35) due to the stabilization of the resultant carbanion by the S(O)R group, and for example are deprotonated with diaminocarbenes. A carbanion is an anion in which carbon has an unshared pair of electrons and bears a negative charge usually with three substituents for a total of eight valence electrons. ...

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: Iodomethane, commonly called methyl iodide, is a dense volatile liquid. ... For sodium in the diet, see Salt. ... Hydride is the name given to the negative ion of hydrogen, H−. Although this ion does not exist except in extraordinary conditions, the term hydride is widely applied to describe compounds of hydrogen with other elements, particularly those of groups 1–16. ... This article is about the chemical element. ... An ylide is a neutral molecule with positive and negative charges on adjacent atoms. ...

(CH₃)₂SO + CH₃I → [(CH₃)₃SO]I

[(CH₃)₃SO]I + NaH → [(CH₃)₂CH₂SO + NaI + H₂

In organic synthesis, DMSO is used as an oxidant,^[2] such as the Pfitzner-Moffatt oxidation and the Swern oxidation.^[3] Organic synthesis is the construction of organic molecules via chemical processes. ... The Pfitzner-Moffatt oxidation is a chemical reaction which describes the oxidation of primary and secondary alcohols by reaction with dicyclohexylcarbodiimide (DCC) and dimethyl sulfoxide (DMSO). ... The mild oxidation of primary or secondary alcohols to aldehydes or ketones with a mixture of oxalyl chloride, dimethylsulfoxide and triethylamine is called the Swern oxidation. ...

Products of ozonolysis, trioxolanes, are quenched with dimethyl sulfide to produce aldehydes and DMSO. In ozonolysis ozone cleaves an alkene into carbonyl compounds. ... Dimethyl sulfide causes that distinctive smell from your St. ... An aldehyde. ...

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.^[4] However, use of DMSO in PCR increases the mutation rate.^{[citation needed]} A strip of eight PCR tubes, each tube contains a 100μl reaction. ... “PCR” redirects here. ... For linguistic mutation, see Apophony. ...

DMSO also sees use as a cryoprotectant, added to cell media in order to prevent the cells dying as they are frozen.^{[citation needed]} Approximately 10% may be used with a slow-freeze method, and the cells may be frozen at -20°C or stored in liquid nitrogen safely. A cryoprotectant is a substance that is used to protect biological tissue from freezing damage (damage due to ice formation). ... A tank of liquid nitrogen, used to supply a cryogenic freezer (for storing laboratory samples at a temperature of about -150 Celsius). ...

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. Without it, up to 90 percent of frozen cells will become inactive. 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. Cryobiology is the study of living organisms, organs, biological tissues or biological cells at low temperatures. ... A cryoprotectant is a substance that is used to protect biological tissue from freezing damage (damage due to ice formation). ... A vitrification experiment for the study of nuclear waste disposal at Pacific Northwest National Labs Vitrification is a process of converting a material into a glass-like amorphous solid which is free of any crystalline structure, either by the quick removal or addition of heat, or by mixing with an... Mouse embryonic stem cells. ... Sketch of bone marrow and its cells Pluripotential hemopoietic stem cells (PHSCs) are stem cells found in the bone marrow. ... Blood plasma is the liquid component of blood, in which the blood cells are suspended. ... Bone marrow transplantation or hematopoietic stem cell transplantation (HSCT) is a medical procedure in the field of hematology and oncology that involves transplantation of hematopoietic stem cells (HSC). ... Sketch of bone marrow and its cells Pluripotential hemopoietic stem cells (PHSCs) are stem cells found in the bone marrow. ...

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. For other uses, see 1963 (disambiguation). ... The University of Oregon is a public university located in Eugene, Oregon. ...

In a 1978 study at the Cleveland Clinic Foundation in Cleveland, Ohio, researchers concluded that DMSO brought significant relief to the majority of the 213 patients with inflammatory genitourinary disorders that were studied.^[5] They recommended DMSO for all inflammatory conditions not caused by infection or tumor in which symptoms were severe or patients failed to respond to conventional therapy. The Cleveland Clinic (formally known as the Cleveland Clinic Foundation) is a multispecialty academic medical center located in Cleveland, Ohio, United States. ... Cleveland redirects here. ... This page is a candidate to be moved to Wiktionary. ... Dimethyl sulfoxide The United States DoDs Defense Modeling and Simulation Office This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ...

Some people report an onion- or garlic-like taste after touching DMSO. (Onion and garlic also derive their stinginess from sulfoxides syn-propanethial-S-oxide and allicin.) In the medical field DMSO is predominantly used as a topical analgesic^{[citation needed]}, a vehicle for topical application of pharmaceuticals, as an anti-inflammatory^[6] and an antioxidant^{[citation needed]}. 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. For other uses, see Onion (disambiguation). ... Binomial name L. Allium sativum L., commonly known as garlic, is a species in the onion family Alliaceae. ... Syn-propanethial-S-oxide is the gas released by onions. ... Allicin is a powerful antibiotic and anti-fungal compound obtained from garlic. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... Anti-inflammatory refers to the property of a substance or treatment that reduces inflammation. ... Space-filling model of the antioxidant metabolite glutathione. ... FDA redirects here. ... Palliative care is any form of medical care or treatment that concentrates on reducing the severity of the symptoms of a disease or slows its progress rather than providing a cure. ... Interstitial cystitis (commonly abbreviated to IC) is a urinary bladder disease of unknown cause characterised by urinary frequency (as often as every 10 minutes), urgency, pressure and/or pain in the bladder and/or pelvis. ... Liniment, from the Latin linere, to anoint, is a medicinal preparation meant for external use, but one that is thinner in consistency than an ointment. ...

Because DMSO increases the rate of absorption of some compounds through organic tissues including skin, it can be used as a drug delivery system. Biological tissue is a collection of interconnected cells that perform a similar function within an organism. ... This article is about the organ. ...

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.^[7] Lactose is a disaccharide found in milk. ... A polymer (from Greek: πολυ, polu, many; and μέρος, meros, part) is a substance composed of molecules with large molecular mass composed of repeating structural units, or monomers, connected by covalent chemical bonds. ... Peptides (from the Greek πεπτος, digestible), are the family of short molecules formed from the linking, in a defined order, of various α-amino acids. ... High-throughput screening (HTS), is a method for scientific experimentation especially used in drug discovery and relevant to the fields of biology and chemistry. ...

History

On September 9, 1965, the Wall Street Journal reported the death of an Irish woman after undergoing DMSO treatment for a sprained wrist^[8] Clinical research using DMSO halted and did not begin again until the National Academy of Sciences (NAS) published findings in favor of DMSO in 1972.^{[citation needed]} In 1978, the FDA approved DMSO for treating interstitial cystis. In 1980, Congress held hearings on claims that the FDA was slow in approving DMSO for other medical uses. In 2007, the FDA granted "fast track" designation on clinical studies of DMSO's use in reducing brain tissue swelling following traumatic brain injury.^{[citation needed]}

Safety

MSDS recommends wearing safety glasses because DMSO can cause chronic damage to the eyes.^[9] Glove selection is important when working with DMSO. Thick rubber gloves are recommended. Nitrile gloves, which are very commonly used in chemical laboratories, have been found to dissolve rapidly with exposure to DMSO.^[10] 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.^[11] Dimethyl sulfoxide can produce an explosive reaction when exposed to acid chlorides; at a low temperature, this reaction produces the oxidant for Swern oxidation. Nitrile rubber is a synthetic rubber co-polymer of acrylonitrile (ACN) and butadiene. ... Sodium cyanide is a highly toxic chemical compound, also known as sodium salt of hydrocyanic acid and cyanogran. ... This article is about the chemical compound. ... The mild oxidation of primary or secondary alcohols to aldehydes or ketones with a mixture of oxalyl chloride, dimethylsulfoxide and triethylamine is called the Swern oxidation. ...

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.^[12] Sewers transport wastewater from buildings to treatment facilities. ... It has been suggested that Anoxic sea water, Oxygen minimum zone, and Hypoxic zone be merged into this article or section. ... Dimethyl sulfide causes that distinctive smell from your St. ...

See also

Wikimedia Commons has media related to:

dimethyl sulfoxide

• Dimethyl sulfide (DMS), the corresponding sulfide
• Dimethyl sulfate (also DMS), the corresponding sulfate: a mutagenic alkylating compound
• Methylsulfonylmethane (MSM), a related chemical often used as a dietary supplement

Dimethyl sulfide causes that distinctive smell from your St. ... Dimethyl sulfate has chemical formula (CH3)2SO4. ... In biology, a mutagen (Latin, literally origin of change) is an agent that changes the genetic information (usually DNA) of an organism and thus increases the number of mutations above the natural background level. ... Alkylation is the transfer of an alkyl group from one molecule to another. ... Methylsulfonylmethane (MSM, or dimethylsulfone) is an organic sulfur compound belonging to a class of chemicals known as sulfones. ...

References