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Dimethyl sulfoxide

Dimethyl sulfoxide Structure
CAS No.
67-68-5
Chemical Name:
Dimethyl sulfoxide
Synonyms
DMSO;DIMETHYL SULPHOXIDE;METHYL SULFOXIDE;suL;Dimexide;(CH3)2SO;Sclerosol;METHYL SULPHOXIDE;dimethylsulfoxyde;dimethyl sulfoxide, anhydrous
CBNumber:
CB7854105
Molecular Formula:
C2H6OS
Molecular Weight:
78.13
MOL File:
67-68-5.mol
MSDS File:
SDS
Modify Date:
2024/6/4 19:18:49

Dimethyl sulfoxide Properties

Melting point 18.4 °C
Boiling point 189 °C(lit.)
Density 1.100 g/mL at 20 °C
vapor density 2.7 (vs air)
vapor pressure 0.42 mm Hg ( 20 °C)
FEMA 3875 | METHYLSULFINYLMETHANE
refractive index n20/D 1.479(lit.)
Flash point 192 °F
storage temp. Store at +5°C to +30°C.
solubility H2O: miscible (completely)
pka 35(at 25℃)
form liquid (temperature dependent)
color clear colorless
Relative polarity 0.444
Odor Mild garlic odor
explosive limit 1.8-63.0%(V)
Odor Type alliaceous
Water Solubility Soluble in water, methanol, acetone, ether, benzene, chloroform.
FreezingPoint 18.4℃
Sensitive Hygroscopic
λmax λ: 285 nm Amax: ≤0.20
λ: 295 nm Amax: ≤0.20
JECFA Number 507
Merck 14,3259
BRN 506008
Dielectric constant 41.9(55℃)
Stability Stable. Incompatible with a very wide range of materials, including acid chlorides, strong acids, strong oxidizing agents, strong reducing agents, phosphorus halides, moisture, copper wool + trichloroacetic acid. Reacts violently with a number of materials - consult a full data sheet before use. Hygroscopic.
InChIKey IAZDPXIOMUYVGZ-UHFFFAOYSA-N
LogP -1.35
CAS DataBase Reference 67-68-5(CAS DataBase Reference)
NIST Chemistry Reference Dimethyl sulfoxide(67-68-5)
EPA Substance Registry System Dimethyl sulfoxide (67-68-5)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08
Signal word  Warning
Hazard statements  H227-H320-H373
Precautionary statements  P210e-P280a-P370+P378a-P403+P235-P501a-P260-P264-P305+P351+P338+P337+P313-P314-P501
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  24/25-37/39-26-36-23
RIDADR  NA 1993 / PGIII
WGK Germany  1
RTECS  PV6210000
3
Autoignition Temperature 215 °C
TSCA  Yes
HS Code  29309070
Toxicity LD50 orally in rats: 17.9 ml/kg (Bartsch)
NFPA 704
2
2 0

Dimethyl sulfoxide price More Price(170)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) W387520 Methyl sulfoxide ≥99%, FG 67-68-5 1SAMPLE ₹5141.88 2022-06-14 Buy
Sigma-Aldrich(India) W387520 Methyl sulfoxide ≥99%, FG 67-68-5 1KG ₹7361 2022-06-14 Buy
Sigma-Aldrich(India) W387520 Methyl sulfoxide ≥99%, FG 67-68-5 10KG ₹20318.53 2022-06-14 Buy
Sigma-Aldrich(India) W387520 Methyl sulfoxide ≥99%, FG 67-68-5 25KG ₹43105.15 2022-06-14 Buy
Sigma-Aldrich(India) D8418 Dimethyl sulfoxide for molecular biology 67-68-5 50ML ₹6808.93 2022-06-14 Buy
Product number Packaging Price Buy
W387520 1SAMPLE ₹5141.88 Buy
W387520 1KG ₹7361 Buy
W387520 10KG ₹20318.53 Buy
W387520 25KG ₹43105.15 Buy
D8418 50ML ₹6808.93 Buy

Dimethyl sulfoxide Chemical Properties,Uses,Production

Description

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.

Chemical Properties

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.

Occurrence

Reported found in apple, raspberry, cabbage, cucumber, onion, tomato, peppermint and spearmint oils, milk, pork liver, beer, rum, cocoa, coffee, black tea, oatmeal, soybean, beetroot, parsnip root, watercress, sweet corn, malt, cooked shrimp and oysters

Uses

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.

Production Methods

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.

Definition

ChEBI: A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.

General Description

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.

Air & Water Reactions

Denser than water and miscible in water.

Reactivity Profile

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.

Health Hazard

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

Flammability and Explosibility

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

Chemical Reactivity

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.

Biological Activity

Solvent with wide ranging applications in biological research.

Environmental Fate

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.

storage

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.

Purification Methods

This colourless, odourless, very hygroscopic liquid, is synthesised from dimethyl sulfide. The main impurity is water, with a trace of dimethyl sulfone. The Karl-Fischer test is applicable. It is dried with Linde types 4A or 13X molecular sieves, by prolonged contact and passage through a column of the material, then distilled under reduced pressure. Other drying agents include CaH2, CaO, BaO and CaSO4. It can also be fractionally crystallised by partial freezing. More extensive purification is achieved by standing overnight with freshly heated and cooled chromatographic grade alumina. It is then refluxed for 4hours over CaO, dried over CaH2, and fractionally distilled at low pressure. For efficiency of desiccants in drying dimethyl sulfoxide see Burfield and Smithers [J Org Chem 43 3966 1978, Sato et al. J Chem Soc, Dalton Trans 1949 1986]. [Reddy Pure Appl Chem 25 459 1969, Beilstein 1 IV 1277.] Rapid purification: Stand over freshly activated alumina, BaO or CaSO4 overnight. Filter and distil it over CaH2 under reduced pressure (~ 12 mm Hg). Store it over 4A molecular sieves.

Incompatibilities

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).

Waste Disposal

Excess dimethyl sulfoxide and waste material containing this substance should be placed in an appropriate container, clearly labeled, and handled according to your institution's waste disposal guidelines.

Regulatory Status

Included in the FDA Inactive Ingredients Database(IVinfusions,SC implants, and topical preparations). Available in the USA as a 50% solution for irrigation in the treatment of interstitial cystitis. Also available in Canada as a 70% solution for use as a topical antifibrotic, and in Germany as a topical gel containing 10% dimethyl sulfoxide for the treatment of musculoskeletal and joint disorders. Included in topical formulations of idoxuridine and diclofenac licensed in the UK.

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