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

A13280 Dimethyl sulfoxide, 99+%

Numéro de CAS
67-68-5
Synonymes
DMSO
Methyl sulfoxide

Conditionnement Prix ($) Quantité Disponibilité
500g 28,80
2500g 69,50
10000g 230,00
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Dimethyl sulfoxide, 99+%

MDL
MFCD00002089
EINECS
200-664-3

Propriétés chimiques

Formule
C2H6OS
Poids moleculaire
78.13
Point de fusion
18.4°
Point d'ébullition
189°
Point d'éclair
87°(189°F)
Densité
1.101
Indice de réfraction
1.4790
Sensibilité
Hygroscopic
Solubilité
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.

Références bibliographiques

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.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H227

Combustible liquid.

Mentions de prudence: P210u-P280a-P370+P378a-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/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.

Autres références

Merck
14,3259
Beilstein
506008
Code tarifaire harmonisé
2930.90
TSCA
Yes
RTECS
PV6210000

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Analytique et matériel de laboratoire