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67-68-5 - Dimethyl sulfoxide, 99+% - DMSO - Methyl sulfoxide - A13280 - Alfa Aesar

A13280 Dimethyl sulfoxide, 99+%

CAS Number
67-68-5
Synonyms
DMSO
Methyl sulfoxide

Size Price ($) Quantity Availability
500g 28.43
2500g 70.86
10000g 234.84
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Dimethyl sulfoxide, 99+%

MDL
MFCD00002089
EINECS
200-664-3

Chemical Properties

Formula
C2H6OS
Formula Weight
78.13
Melting point
18.4°
Boiling Point
189°
Flash Point
87°(189°F)
Density
1.101
Refractive Index
1.4790
Sensitivity
Hygroscopic
Solubility
Miscible with water, ethanol, ether, benzene, chloroform and acetone.

Applications

Dimethyl Sulfoxide (DMSO) is used as a solvent for chemical reactions involving salts, most notably in Finkelstein reactions and in other nucleophilic substitutions. DMSO is an effective pain relieving agent. It is also used in antifreeze or hydraulic fluids and utilized in the oxidation of thiols and disulfides to sulfonic acids. It is used to enhance dermal absorption of many chemicals. It is also used as a cryoprotectant and is added to cell media to reduce ice formation and thereby prevent cell death during the freezing process.

Notes

Hygroscopic. Incompatible with acid chlorides, phosphorus halides, strong acids, strong oxidizing agents and strong reducing agents.

Literature References

Dipolar aprotic solvent with advantages over e.g. N,N-Dimethyl­formamide, A13547, 1-Methyl-2-pyrrolidinone, A12260 of lower toxicity and generally higher solvent power for many types of material.

Powerful solvent for many inorganic ions, primarily due to solvation of the cations with consequent enhanced reactivity of the counter anions both in increased nucleophilicity and base strength. In DMSO, the relative nucleophilicities of the halide ions are reversed (F- > I-). The rate of aromatic fluorodenitration in a range of polar aprotic solvents was highest for DMSO: J. Fluorine Chem., 35, 591 (1987); see Potassium fluoride, 14130. For enhanced base strength, see e.g.: cyclization of ω-bromo acids to lactones by K2CO3: Org. Synth. Coll., 6, 698 (1988); exhaustive alkylation of ketones with KOH: Tetrahedron Lett., 31, 859 (1990).

Malonic and ß-keto esters can be conveniently decarboalkoxylated by heating in wet DMSO: J. Org. Chem., 43, 138 (1978), avoiding the need for separate hydrolysis and decarboxylation steps.

Tosylates or activated halides can be oxidized with DMSO to aldehydes and ketones (Kornblum oxidation). ɑ-Bromo ketones are oxidized at room temperature to ɑ-keto aldehydes: J. Am .Chem. Soc., 79, 6562 (1957). Benzylic halides, on heating in the presence of NaHCO3, give benzaldehydes: J. Am. Chem. Soc., 114, 6227 (1992). Under similar conditions at 150oC, primary alkyl iodides: J. Chem. Soc., 520 (1964), and alkyl chlorides and bromides in the presence of NaI: Synth. Commun., 16, 1343 (1986), are oxidized to aldehydes. Unactivated bromides have also been oxidized to aldehydes in the presence of Ag salts: Tetrahedron Lett., 917 (1974). For oxidation of benzyl alcohols to benzaldehydes, catalyzed by HBr, see: Synlett, 2041 (2002). DMSO is more often used in combination with a variety of activating agents for selective oxidation of primary and secondary alcohols to carbonyl compounds under very mild conditions. For examples, see: Oxalyl­ chloride, A18012, or Trifluoroacetic anhydride, A13614 (Swern oxidation), Acetic anhydride, L04295 (Albright-Goldman), N,N'-Dicyclohexyl­carbodiimide, A10973 (Pfitzner-Moffatt), Sulfur trioxide-pyridine complex, A12202 (Parikh-Doering), Triphosgene, A14932 and Phenyl­ phosphorodichloridate, A10479. Reviews: Synthesis, 70 (1971); 165 (1981); 857 (1990).

DMSO is a very weak acid (pKa= 31) but can be deprotonated by NaH, giving "dimsyl sodium", which is a useful strong base e.g. for the Wittig reaction: J. Org. Chem., 28, 1128 (1963).

Aromatic amines can be substituted in the para-position by reaction with DMSO in the presence of conc. HCl with or without CuCl to give 4-aminobenzaldehydes: J. Chem. Soc., Perkin 1, 2235 (1992). The intermediate species is thought to be chloromethyl methyl sulfoxide.

Mozhzhukhina, N.; Longinotti, M. P.; Corti, H. R.; Calvo, E. J. A conductivity study of preferential solvation of lithium ion in acetonitrile-dimethyl sulfoxide mixtures. Electrochim. Acta 2015, 154, 456-461.

Song, S.; Huang, X.; Liang, Y. F.; Tang, C.; Li, X.; Jiao, N. From simple organobromides or olefins to highly value-added bromohydrins: a versatile performance of dimethyl sulfoxide. Green Chem. 2015, 17 (5), 2727-2731.

GHS Hazard and Precautionary Statements

Hazard Statements: H227

Combustible liquid.

Precautionary Statements: P210-P280-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. In case of fire: Use for extinction: CO2, powder or water spray. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,3259
Beilstein
506008
Harmonized Tariff Code
2930.90
TSCA
Yes
RTECS
PV6210000

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