276855

Sigma-Aldrich

Dimethyl sulfoxide

anhydrous, ≥99.9%

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

Quality Level

grade

anhydrous

vapor density

2.7 (vs air)

vapor pressure

0.42 mmHg ( 20 °C)

assay

≥99.9%

form

liquid

autoignition temp.

573 °F

expl. lim.

42 %, 63 °F

impurities

<0.005% water

evapn. residue

<0.0005%

color

colorless

refractive index

n20/D 1.479 (lit.)

bp

189 °C (lit.)

mp

16-19 °C (lit.)

solubility

H2O: miscible (completely)

density

1.10 g/mL (lit.)

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 is an apolar protic solvent that is generally used as a reaction medium and reagent in organic reactions.

Application

Dimethyl Sulfoxide may be used as an oxidant for the conversion of isonitriles into isocyanates. DMSO activated by oxalyl chloride can be used in the oxidation of long-chain alcohols to carbonyls.

Packaging

20 L in Pure-Pac™ 2
100, 12×100 mL in Sure/Seal™
1, 6×1, 2 L in Sure/Seal™
200 L in Pure-Pac™ 1
18 L in Pure-Pac™ 1

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
Pure-Pac® II containers require the Micromatic MacroValve coupler for dispensing solvents, Z560723.
The article number 276855-4X2L will be discontinued. Please order the single bottle 276855-2L which is physically identical with the same exact specifications.

Legal Information

Pure-Pac is a registered trademark of Sigma-Aldrich Co. LLC

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

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

  1. What is the molarity of DMSO?

    DMSO will have a molarity of 14.1M, based on a density of 1.1 g/mL and a molecular weight of 78.13 g/mol.

  2. What is the DMSO dissolved in?

    DMSO is not dissolved in any solvent. It is a pure chemical compound that is a liquid at room temperature.

  3. Where does DMSO come from?

    DMSO is known to have been isolated from tree bark in the past. It is now a commericially synthesized solvent.

  4. Does DMSO have any synthetic utility?

    DMSO has been used to oxidize thiols and disulfides to sulfonic acids, hydrolysis of epoxides, thioalkylation of phenols, and oxidation of primary alcohols and halides, and esters of primary alcohols to aldehydes.

  5. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  6. Dimethyl sulfoxide (DMSO) should be a liquid.  Why did it arrive as a solid?

    DMSO supercools easily, and re-melts slowly at room temperature. The melting point is 16-19 °C. The solidified product can be re-liquefied by warming to room temperature without detriment to the product.

  7. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is Sure/Seal packaging?

    The Aldrich Sure/Seal packaging system is useful in the handling and storage of air-sensitive reagents.

  10. Is Dimethyl sulfoxide a sterile product?

    No, this product is not considered sterile.  Product Nos. D2560 and D2438 are sterile-filtered.

A Practical Synthesis of Isocyanates from Isonitriles: Ethyl 2-Isocyanatoacetate
Hoang VLe and Ganem B
Organic Syntheses, 89, 404-404 (2012)
Dimethyl sulfoxide oxidations.
Epstein WW & Sweat FW.
Organic Syntheses, 67(3), 247-260 (1967)
The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals
Royal Society of Chemistry null
Michael Maurer et al.
Cell chemical biology, 26(8), 1169-1179 (2019-06-18)
ATP-driven bacterial AAA+ proteases have been recognized as drug targets. They possess an AAA+ protein (e.g., ClpC), which threads substrate proteins into an associated peptidase (e.g., ClpP). ATPase activity and substrate selection of AAA+ proteins are regulated by adapter proteins...
Oxidation of long-chain and related alcohols to carbonyls by dimethyl sulfoxide" activated" by oxalyl chloride.
Mancuso AJ, et al.
The Journal of Organic Chemistry, 43(12), 2480-2482 (1978)
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