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. 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 They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 13 g/mol
Appearance	Clear, colorless liquid
Density	1. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 1004 g/cm3, liquid
Melting point	18. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. 5 °C (292 K)
Boiling point	189 °C (462 K)
Solubility in water	Miscible
Acidity (pKa)	35
Refractive index (nD)	1. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 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 479 εr = 48
Viscosity	1. Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 996 cP at 20 °C
Structure
Dipole moment	3. The poise (symbol P pwɑːz is the unit of dynamic Viscosity in the Centimetre gram second system of units. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 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. The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance This page provides supplementary chemical data on Dimethyl sulfoxide A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning 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. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air A sulfoxide is a Chemical compound containing a sulfinyl Functional group attached to two carbon atoms Diethyl sulfoxide, C4H10OS is a Sulfur -containing Organic compound. Sodium methylsulfinylmethylide (also called NaDMSO) is the Conjugate base of Dimethyl sulfoxide. Dimethyl sulfide (DMS or methylthiomethane is an organosulfur compound with the formula (CH32S Methylsulfonylmethane (MSM or dimethylsulfone is an Organosulfur compound with the formula (CH32SO2 Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless mobile flammable 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 Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test
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 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 in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles 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 a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes 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. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. In Chemistry a protic solvent is a Solvent that has a Hydrogen atom bound to an Oxygen as in a Hydroxyl group or a Nitrogen Miscibility is a term commonly used in Chemistry that refers to the property of Liquids to mix in all proportions forming a Homogeneous Solution 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. The common name oyster is used for a number of different groups of Bivalve Mollusks most of which live in marine habitats or Brackish water. 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. Wood pulp is a dry fibrous material prepared by chemically or mechanically separating the fibers which make up Wood. A supplier of DMSO is the Gaylord Chemical Corporation in the USA. Gaylord Chemical Corporation is based in the New Orleans suburb of Slidell, Louisiana. The United States of America —commonly referred to as the

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. In Chemistry a protic solvent is a Solvent that has a Hydrogen atom bound to an Oxygen as in a Hydroxyl group or a Nitrogen It is less toxic than other members of this class such as dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, HMPA. Dimethylformamide is the Organic compound with the formula ( CH3)2NC(OH Dimethylacetamide is the Organic compound with the formula CH3C(ON(CH32 N -Methyl-2-pyrrolidone (NMP is a Chemical compound with 5-membered Lactam structure Hexamethylphosphoramide (abbreviated HMPA is a colorless organic liquid with the formula 3PO 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. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. The Finkelstein reaction, named for the German chemist Hans Finkelstein, is an SN2 reaction that involves the exchange of one Halogen atom for In organic and Inorganic chemistry, nucleophilic substitution is a fundamental class of Substitution reaction in which an "electron rich" 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. 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 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]

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. Paint stripper, or paint remover, is the generic name given to Solvent mixtures designed to remove Paint and other finishes and also to clean the underlying Nitromethane is an Organic compound with the chemical formula CH3NO2 Dichloromethane ( DCM) or methylene chloride is the Chemical compound with the formula CH2Cl2 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).

In its deuterated form, i. Deuterium, also called heavy hydrogen, is a Stable isotope of Hydrogen with a Natural abundance in the Oceans of Earth 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. Deuterated DMSO ((CD32S=O is a form (called an Isotopologue) of Dimethyl sulfoxide (DMSO (CH32S=O in which the 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. Deuterated chloroform (CDCl3 is an Isotopologue of Chloroform (CHCl3 in which the Hydrogen atom ("H" is replaced with

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 A persistent carbene (also known as a stable carbene or an Arduengo carbene is a type of Carbene demonstrating particular stability despite also being a Reactive

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 → [(CH₃)₂CH₂SO + NaI + H₂

In organic synthesis, DMSO is used as an oxidant,^[2] such as the Pfitzner-Moffatt oxidation and the Swern oxidation. Iodomethane, commonly called Methyl iodide and commonly abbreviated "MeI" is the Chemical compound with the formula CH3I Sodium (ˈsoʊdiəm is an element which has the symbol Na( Latin natrium, from Arabic natrun) atomic number 11 atomic mass 22 Hydride is the name given to the negative Ion of Hydrogen, H− Sulfur or sulphur (ˈsʌlfɚ see spelling below) is the Chemical element that has the Atomic number 16 An ylid or ylide (US is a neutral Molecule with a positive and a negative charge on adjacent Atoms They appear in Organic chemistry Organic synthesis is a special branch of Chemical synthesis and is concerned with the construction of Organic compounds via Organic reactions Organic The Pfitzner-Moffatt oxidation, sometimes referred to as simply the Moffatt oxidation, is a Chemical reaction which describes the oxidation of primary and The Swern oxidation, named after Daniel Swern, is a Chemical reaction whereby a primary or secondary Alcohol is oxidized to an Aldehyde ^[3]

Products of ozonolysis, trioxolanes, are quenched with dimethyl sulfide to produce aldehydes and DMSO. Ozonolysis is the cleavage of an Alkene or Alkyne with Ozone to form Organic compounds in which the multiple Carbon-carbon bond has Dimethyl sulfide (DMS or methylthiomethane is an organosulfur compound with the formula (CH32S An aldehyde is an organic compound containing a terminal Carbonyl group.

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. In biology mutations are changes to the Nucleotide sequence of the Genetic material of an organism

DMSO also sees use as a cryoprotectant, added to cell media in order to prevent the cells dying as they are frozen. A cryoprotectant is a substance that is used to protect Biological tissue from Freezing damage (damage due to Ice formation 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. Liquid nitrogen (liquid density at the Triple point is 0707 g/mL is the liquid produced industrially in large quantities by Fractional distillation of

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. Cryobiology is the branch of Biology that studies the effects of low Temperatures on living things A cryoprotectant is a substance that is used to protect Biological tissue from Freezing damage (damage due to Ice formation Vitrification is a process of converting a material into a Glass -like Amorphous solid that is free from any Crystalline structure either by the quick removal 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. Embryonic stem cells (ES cells are Stem cells derived from the inner cell mass of an early stage Embryo known as a Blastocyst. Hematopoietic stem cells (HSCs are Stem cells that give rise to all the blood cell types including Myeloid ( Monocytes and Macrophages, Neutrophils Blood plasma is the Liquid component of Blood, in which the Blood cells are suspended As part of an autologous bone marrow transplant the DMSO is re-infused along with the patient's own hematopoietic stem cells. Hematopoietic stem cells (HSCs are Stem cells that give rise to all the blood cell types including Myeloid ( Monocytes and Macrophages, Neutrophils

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. Year 1963 ( MCMLXIII) was a Common year starting on Tuesday (link will display full calendar of the Gregorian calendar. The University of Oregon (UO is a public, Coeducational Research university in Eugene Oregon, United States.

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. The Cleveland Clinic (formally known as the Cleveland Clinic Foundation) is a multispecialty academic medical center located in Cleveland, Ohio, Cleveland is a City in the US state of Ohio and the County seat of Cuyahoga County, the most populous county in the state In Anatomy, the genitourinary system is the Organ system of all the Reproductive organs and the Urinary system. ^[4] 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.

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. Organicsalsajpg||thumb|right|Onions used in salsa.]]Cooked onions in frying pan Allium sativum L, commonly known as garlic, is a species in the Onion family Alliaceae. Syn-propanethial-S-oxide is a volatile gas that triggers tears when an Onion is cut Allicin is an Organic compound obtained from Garlic. This colourless liquid has a distinctively pungent smell ) In the medical field DMSO is predominantly used as a topical analgesic, a vehicle for topical application of pharmaceuticals, as an anti-inflammatory^[5] and an antioxidant. Anti-inflammatory refers to the property of a substance or treatment that reduces Inflammation. An antioxidant is a Molecule capable of slowing or preventing the oxidation of other molecules 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. Palliative care (from Latin palliare to cloak is any form of medical care or treatment that concentrates on reducing the severity of Disease Symptoms Interstitial cystitis (commonly abbreviated to "IC" is a Urinary bladder Disease of unknown cause characterised by urinary frequency (as often as every Also, DMSO is commonly used in the veterinary field as a liniment for horses. Liniment, (or embrocation from the Latin linere, to Anoint, is a medicated topical preparation for application to the skin

Because DMSO increases the rate of absorption of some compounds through organic tissues including skin, it can be used as a drug delivery system. Tissue is a cellular organizational level intermediate between cells and a complete organism The skin is the outer covering of living tissue of an animal (or plant

Dimethyl sulfoxide dissolves a variety of organic substances, including carbohydrates, polymers, peptides, as well as many inorganic salts and gases. Carbohydrates (from ' Hydrates of Carbon ' or saccharides ( Greek σάκχαρον meaning " Sugar " are the most A polymer is a large Molecule ( Macromolecule) composed of repeating Structural units typically connected by Covalent Chemical bonds Peptides (from the Greek πεπτίδια, "small digestibles" are short Polymers formed from the linking in a defined order of α- Amino 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. High-throughput screening (HTS is a method for scientific Experimentation especially used in Drug discovery and relevant to the fields of Biology and ^[6]

History

On September 9, 1965, the Wall Street Journal reported the death of an Irish woman after undergoing DMSO treatment for a sprained wrist^[7] 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. 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.

Safety

MSDS recommends wearing safety glasses because DMSO can cause chronic damage to the eyes. ^[8] 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. Nitrile rubber or Buna-N, is a Synthetic rubber Copolymer of Acrylonitrile (ACN and Butadiene. ^[9] 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. Sodium cyanide is the Inorganic compound with the formula NaCN A cyanide is any Chemical compound that contains the cyano group (C≡N which consists of a Carbon Atom triple-bonded to a DMSO by itself has low toxicity. ^[10] Dimethyl sulfoxide can produce an explosive reaction when exposed to acid chlorides; at a low temperature, this reaction produces the oxidant for Swern oxidation. The Swern oxidation, named after Daniel Swern, is a Chemical reaction whereby a primary or secondary Alcohol is oxidized to an Aldehyde

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. For other uses of the term "hypoxia" see Hypoxia. Hypoxia or oxygen depletion is a phenomenon that occurs in aquatic environments Dimethyl sulfide (DMS or methylthiomethane is an organosulfur compound with the formula (CH32S ^[11]

See also

• 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

References