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Home > Encyclopedia > Dimethyl sulfoxide

Dimethyl sulfoxide

pharmaceutical raw materials
Dimethyl sulfoxide structure

Dimethyl sulfoxide 

structure
  • CAS No:

    67-68-5

  • Formula:

    C2H6OS

  • Chemical Name:

    Dimethyl sulfoxide

  • Synonyms:

    sulfinylbis (methane);DMSO;DIMETHYL SULFOXIDE;DIMETHYL SULPHOXIDE;DIMETHYLIS SULFOXIDUM;FEMA 3875;Methyl sulfoxide, extra pure, 99.85%;Methyl sulfoxide, for analysis ACS, 99.9+%

  • Categories:

    Organic Chemistry  >  Organosulfur Compounds

Description

It is colorless liquid, and is hygroscopic. It is almost odorless with a bitter taste. It can be dissolved in water, ethanol, acetone, ether, benzene and chloroform.


First synthesized in 1866 by Alexander Zaytsev in the Russian Empire, dimethyl sulfoxide is an organosulfur compound. 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.


Dimethyl sulfoxide occurs as a colorless, viscous liquid, or as colorless crystals that are miscible with water, alcohol, and ether. The material hasa slightly bitter taste with a sweet aftertaste, and is odorless, or has a slight odor characteristic of dimethyl sulfoxide.Dimethyl sulfoxide is extremely hygroscopic, absorbing up to 70% of its own weight in water with evolution of heat.


ChEBI: Dimethyl sulfoxide is a 2-carbon sulfoxide in which the sulfur atom has two methyl substituents. It has a role as a polar aprotic solvent, a radical scavenger, a non-narcotic analgesic, an antidote, a MRI contrast agent, an Escherichia coli metabolite, a geroprotector and an alkylating agent. It is a sulfoxide and a volatile organic compound.


A clear liquid, essentially odorless. Closed cup flash point 192°F. Vapors are heavier than air. Contact with the skin may cause stinging and burning and lead to an odor of garlic on the breath. An excellent solvent that can transport toxic solutes through the skin. High vapor concentrations may cause headache, dizziness, and sedation.

Dimethyl sulfoxide Basic Attributes

78.13

506008

200-664-3

TSCA listed

clear colorless

29309070

Characteristics

λ: 285 nm Amax: ≤0.20λ: 295 nm Amax: ≤0.20

Reactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

1.100 g/mL at 20 °C

18.4 °C

189 °C(lit.)

n20/D1.479(lit.)

Soluble in water, methanol, acetone, ether, benzene, chloroform.

0.42 mm Hg ( 20 °C)

2.7 (vs air)

LD50 orally in rats: 17.9 ml/kg (Bartsch)

Combustible when exposed to heat or flame (NFPA rating = 1). Carbon dioxide or dry chemical extinguishers should be used to fight DMSO fires.

Mild garlic odor

35(at 25℃)

9.8×102mol/(m3Pa) at 25℃, Burkholder et al. (2019)

Denser than water and miscible in water.

Dimethyl sulfoxide decomposes violently on contact with many acyl halides, aryl halides and related compounds such as phenyl and tolyl chloride, acetyl chloride, benzenesulfonyl chloride, benzoyl chloride, cyanuric chloride, phosphorus chloride, phosphorus oxychloride, and thionyl chloride [Chem. Eng. News 35(9):87 (1957)]. Reacts, possibly violently, with iodine pentafluoride [Chem. Eng. News 47(12):, 109(1969)]. Vacuum distillation from anhydrous magnesium perchlorate led to an explosion [MCA Case History 1187(1966)]. Violently reactive with fluorinating agents such as silver fluoride [Chem. Eng. News 44(24):7(1956)]. Can explode with sodium hydride [Chem. Eng. News 44(24):7(1966)]. Mixture with methyl bromide resulted in an explosion that shattered the apparatus [NFPA 491M, 1991]. Forms salts with perchloric acid that are explosive when dry [Chem. Abst. 44:p3935d (1950)]. Decomposes when heated above normal boiling point.

215 °C

Store at +5°C to +30°C.

Safety Information

CBL

1

Xi

24/25-37/39-26-36-23

PV6210000

Dimethyl sulfoxide is reasonably stable to heat,but upon prolonged reflux it decomposes slightly to methyl mercaptan and bismethylthiomethane. This decomposition is aided by acids, and is retarded by many bases. When heated to decomposition, toxic fumes are emitted.At temperatures between 40 and 60°C, it has been reported that dimethyl sulfoxide suffers a partial breakdown, which is indicated by changes in physical properties such as refractive index, density, and viscosity.Dimethyl sulfoxide should be stored in airtight, light-resistant containers. The PhEur 6.0 states that glass containers should be used. Contact with plastics should be avoided.

36/37/38

DMSO reacts violently with strong oxidizers, many acyl halides, boron hydrides, and alkali metals. DMSO can form explosive mixtures with metal salts of oxoacids (sodium perchlorate, iron(III) nitrate).

NA 1993 / PGIII

Toxicity

Most physiological properties of DMSO appear to be related to its penetration properties, its potential to inhibit or stimulate enzymes and to act as a free radical scavenger, and its ability to cause histamine release from mast cells. These properties are largely based on DMSO’s chemical characteristics, including its hydrogen bonding behavior, water affinity, ability to interchange with water in membranes, and ability to react with organic molecules.

Drug Information

The acute toxicity of DMSO by all routes of exposure is very low. Inhalation of DMSO vapor can cause irritation of the respiratory tract, and at higher concentrations may cause vomiting, chills, headache, and dizziness. The material is only slightly toxic by ingestion and may cause vomiting, abdominal pain, and lethargy. Dimethyl sulfoxide is relatively nontoxic by skin absorption, but can cause itching, scaling, and a transient burning sensation. Dimethyl sulfoxide can increase the tendency for other chemicals to penetrate the skin and so increase their toxic effects. Contact of DMSO liquid with the eyes may cause irritation with redness, pain, and blurred vision. Chronic exposure to dimethyl sulfoxide can cause damage to the cornea of the eye. Dimethyl sulfoxide has not been found to be carcinogenic or to show reproductive or developmental toxicity in humans

Dimethyl sulfoxide Use and Manufacturing

Uses

1. It can be used for the extraction of arene, also as the reaction medium used for resins and dyes, and applied to acrylic polymerization and spinning solvent.2. It can be used as an organic solvent, reaction medium and the intermediates of organic synthesis. It is highly versatile. This product has a highly selective extraction capacity, and can be used as the polymerization and condensation solvent of acrylic resin and polysulfone resin, as the polymerization and spinning solvent of polyacrylonitrile and cellulose acetate, as the extraction solvent for separating alkanes and arenes, and as the reaction medium for the arenes, butadiene extraction, acrylic fiber, plastic solvents, organic and synthetic dyes, and pharmaceuticals industries. In the field of medicine, dimethyl sulfoxide has anti-inflammatory and analgesic effect with a strong capability of penetration through the skin, and thus being able to dissolve certain drugs and boost their penetration into the human body to achieve the therapeutic purposes. Taking this carrier property of dimethyl sulfoxide can make it be used as pesticide additives. Add a small amount of dimethyl sulfoxide in some pesticides can facilitate the penetration of pesticides into the plant in order to improve the efficacy. dimethyl sulfoxide can also be used as the dye solvent, dye removing agent, and dye carrier for the synthetic fibers. It can also be used as the absorbent of recycling acetylene and sulfur dioxide and also the modifiers of synthetic fiber, antifreeze agent and the capacitor dielectric, brake oil, and extractant of the rare metals.3. It can be used as analytic solvents and fixing agent of gas chromatography as well as the solvent for analyzing UV spectra.


DMSO is a polar aprotic solvent used in chemical reactions, in polymerase chain reactions (PCR) and as a cryoprotectant vitrification agent for the preservation of cells, tissues and organs. DMSO is used in cell freezing media to protect cells from ice crystal induced mechanical injury. It is used for frozen storage of primary, sub-cultured, and recombinant heteroploid and hybridoma cell lines; embryonic stem cells (ESC), and hematopoietic stem cells. DMSO is frequently used in the combinations with BSA or fetal bovine serum (FBS).


Human and animal cell lines grown in culture are generally stored frozen. Freezing protects the cell line from changes due to genetic drift and minimizes risk of contamination. Liquid nitrogen used in conjunction with a cryoprotective agent such as DMSO is a widely used method for preserving cells. Without the presence of a cryoprotective agent, freezing is lethal to most mammalian cells. Damage is caused by mechanical injury by ice crystals, concentration of electrolytes, pH changes, and denaturation of proteins. These lethal effects are minimized by adding a cryoprotective agent which lowers


Dimethyl sulfoxide (1-10%) has been shown to accelerate strand renaturation and is believed to give the nucleic acid thermal stability against depurination. As a PCR cosolvent, DMSO may help improve yields, especially in long PCR.


A polar aprotic solvent used in polymerase chain reactions (PCR) and as a cryoprotectant vitrification agent for the preservation of cells, tissues and organs.

Production

Dimethyl sulfoxide is prepared by air oxidation of dimethyl sulfide in the presence of nitrogen oxides. It can also be obtained as a by product of wood pulp manufacture for the paper and allied industries.

Drug Function and Efficacy

Penetration enhancer, anti-inflammatory, analgesic

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

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