Dimethyl sulfoxide

Dimethyl sulfoxide
Stereo structural formula of dimethyl sulfoxide with an explicit electron pair and assorted dimensions	Spacefill model of dimethyl sulfoxide
	; A sample of dimethyl sulfoxide
Names
	Preferred IUPAC name (Methanesulfinyl)methane
	Systematic IUPAC name (Methanesulfinyl)methane (substitutive); Dimethyl(oxido)sulfur (additive)
	Other names Methylsulfinylmethane; Methyl sulfoxide (2:1), Dermasorb
Identifiers
CAS Number	67-68-5 ;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	DMSO, Me2SO
Beilstein Reference	506008
ChEBI	CHEBI:28262 ;
ChEMBL	ChEMBL504 ;
ChemSpider	659 ;
DrugBank	DB01093 ;
ECHA InfoCard	100.000.604
EC Number	200-664-3;
Gmelin Reference	1556
KEGG	D01043 ;
MeSH	Dimethyl+sulfoxide
PubChem CID	679;
RTECS number	PV6210000;
UNII	YOW8V9698H ;
CompTox Dashboard (EPA)	DTXSID2021735 ;
	InChI InChI=1S/C2H6OS/c1-4(2)3/h1-2H3 Key: IAZDPXIOMUYVGZ-UHFFFAOYSA-N ; InChI=1/C2H6OS/c1-4(2)3/h1-2H3 Key: IAZDPXIOMUYVGZ-UHFFFAOYAR;
	SMILES CS(=O)C; CS(C)=O;
Properties
Chemical formula	C2H6OS
Molar mass	78.13 g·mol−1
Appearance	Colourless liquid
Density	1.1004 g⋅cm−3
Melting point	19 °C (66 °F; 292 K)
Boiling point	189 °C (372 °F; 462 K)
Solubility in water	Miscible
Solubility in Diethyl ether	Not soluble
Vapor pressure	0.556 millibars or 0.0556 kPa at 20 °C
Acidity (pKa)	35
Refractive index (nD)	1.479; εr = 48
Viscosity	1.996 cP at 20 °C
Structure
Point group	Cs
Molecular shape	Trigonal pyramidal
Dipole moment	3.96 D
Pharmacology
ATC code	G04BX13 (WHO) M02AX03 (WHO)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Irritant
NFPA 704 (fire diamond)	1 2 0
Flash point	89 °C (192 °F; 362 K)
Safety data sheet (SDS)	Oxford MSDS
Related compounds
Related sulfoxides	Diethyl sulfoxide
Related compounds	Sodium methylsulfinylmethylide,; Dimethyl sulfide,; Dimethyl sulfone,; Acetone;
Supplementary data page
	Dimethyl sulfoxide (data page)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH₃)₂S O. This colorless liquid is the sulfoxide most widely used commercially. It 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. It has a relatively high boiling point. DMSO is metabolised to compounds that leave a garlic-like taste in the mouth after DMSO is absorbed by skin.^[5]

In terms of chemical structure, the molecule has idealized C_s symmetry. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds,^[6] with a nonbonded electron pair on the approximately tetrahedral sulfur atom.

^ DMSO (medication)
^ "Dimethyl Sulfoxide (DMSO) -- Technical". Atofina Chemicals, inc. Retrieved 26 May 2007.
^ Matthews WS, Bares JE, Bartmess JE, Bordwell FG, Cornforth FJ, Drucker GE, Margolin Z, McCallum RJ, McCollum GJ, Vanier NR (1975). "Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution". J. Am. Chem. Soc. 97 (24): 7006–7014. doi:10.1021/ja00857a010.
^ "Dimethyl sulfoxide". pubchem.ncbi.nlm.nih.gov.
^ Novak KM, ed. (2002). Drug Facts and Comparisons (56th ed.). St. Louis, Missouri: Wolters Kluwer Health. p. 2345. ISBN 978-1-57439-110-7.
^ Thomas R, Shoemaker CB, Eriks K (1966). "The Molecular and Crystal Structure of Dimethyl Sulfoxide, (H₃C)₂SO". Acta Crystallogr. 21 (1): 12–20. Bibcode:1966AcCry..21...12T. doi:10.1107/S0365110X66002263.

[1] DMSO (medication)

[Atofina-2] "Dimethyl Sulfoxide (DMSO) -- Technical". Atofina Chemicals, inc. Retrieved 26 May 2007.

[3] Matthews WS, Bares JE, Bartmess JE, Bordwell FG, Cornforth FJ, Drucker GE, Margolin Z, McCallum RJ, McCollum GJ, Vanier NR (1975). "Equilibrium acidities of carbon acids. VI. Establishment of an absolute scale of acidities in dimethyl sulfoxide solution". J. Am. Chem. Soc. 97 (24): 7006–7014. doi:10.1021/ja00857a010.

[4] "Dimethyl sulfoxide". pubchem.ncbi.nlm.nih.gov.

[5] Novak KM, ed. (2002). Drug Facts and Comparisons (56th ed.). St. Louis, Missouri: Wolters Kluwer Health. p. 2345. ISBN 978-1-57439-110-7.

[6] Thomas R, Shoemaker CB, Eriks K (1966). "The Molecular and Crystal Structure of Dimethyl Sulfoxide, (H₃C)₂SO". Acta Crystallogr. 21 (1): 12–20. Bibcode:1966AcCry..21...12T. doi:10.1107/S0365110X66002263.

[1]

[2]

[3]

[5]

[6]