41640

Sigma-Aldrich

Dimethyl sulfoxide

puriss. p.a., ACS reagent, ≥99.9% (GC)

Synonym(s):
DMSO
Linear Formula:
(CH3)2SO
CAS Number:
Molecular Weight:
78.13
Beilstein/REAXYS Number:
506008
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

ACS reagent
puriss. p.a.

vapor density

2.7 (vs air)

vapor pressure

0.42 mmHg ( 20 °C)

assay

≥99.9% (GC)

form

liquid

autoignition temp.

573 °F

expl. lim.

42 %, 63 °F

impurities

≤0.001% free acid (as CH3COOH)
≤0.1% water

evapn. residue

≤0.005%

refractive index

n20/D 1.479 (lit.)
n20/D 1.479

bp

189 °C (lit.)

mp

16-19 °C (lit.)
18-20 °C

density

1.10 g/mL (lit.)

cation traces

Al: ≤0.5 mg/kg
Ba: ≤0.1 mg/kg
Bi: ≤0.1 mg/kg
Ca: ≤0.5 mg/kg
Cd: ≤0.05 mg/kg
Co: ≤0.02 mg/kg
Cr: ≤0.02 mg/kg
Cu: ≤0.02 mg/kg
Fe: ≤0.5 mg/kg
K: ≤0.5 mg/kg
Li: ≤0.1 mg/kg
Mg: ≤0.1 mg/kg
Mn: ≤0.02 mg/kg
Mo: ≤0.1 mg/kg
Na: ≤1 mg/kg
Ni: ≤0.5 mg/kg
Pb: ≤0.1 mg/kg
Sr: ≤0.1 mg/kg
Zn: ≤0.1 mg/kg

SMILES string

CS(C)=O

InChI

1S/C2H6OS/c1-4(2)3/h1-2H3

InChI key

IAZDPXIOMUYVGZ-UHFFFAOYSA-N

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General description

Dimethyl sulfoxide (DMSO) is a polar solvent. DMSO activated by electrophile (oxalyl chloride) has been used to oxidize various alcohols (primary, secondary, allylic, benzylic, hindered and bicyclic). Carbonyl compounds are formed as reaction products. It has been proposed as an alternate solvent for methyl cellosolve for use in ninhydrin reaction, due to its high stability.

Caution

Supercools easily and remelts slowly at room temperature. Solidified product can be re-liquified by warming to room temperature without detriment to the product.

Other Notes

For information on dimethyl sulfoxide miscibility, please visit the following link:
Dimethyl Sulfoxide Miscibility/Immiscibility Table
Use as reagent in synthesis

storage_class_code

10 - Combustible liquids

WGK Germany

WGK 1

Flash Point(F)

188.6 °F - closed cup

Flash Point(C)

87 °C - closed cup

Certificate of Analysis

Certificate of Origin

A.J. Mancuso et al.
Synthesis, 165-165 (1981)
Birgit Dreier et al.
Methods in molecular biology (Clifton, N.J.), 805, 261-286 (2011-11-19)
Ribosome display has proven to be a powerful in vitro selection and evolution method for generating high-affinity binders from libraries of folded proteins. It has been successfully applied to single-chain Fv fragments of antibodies and alternative scaffolds, such as Designed...
A RAPID PERMETHYLATION OF GLYCOLIPID, AND POLYSACCHARIDE CATALYZED BY METHYLSULFINYL CARBANION IN DIMETHYL SULFOXIDE.
S HAKOMORI
Journal of biochemistry, 55, 205-208 (1964-02-01)
Oxidation of alcohols by ?activated? dimethyl sulfoxide. A preparative, steric and mechanistic study.
Omura K and Swern D.
Tetrahedron, 34(11), 1651-1660 (1978)
Amino acid analysis: aqueous dimethyl sulfoxide as solvent for the ninhydrin reaction.
S Moore
The Journal of biological chemistry, 243(23), 6281-6283 (1968-12-10)

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