Difference Between DMF and DMSO

The key difference between DMF and DMSO is that DMF is an amide, whereas DMSO is an organosulfur compound.

The term DMF stands for dimethyl formamide while DMSO stands for dimethyl sulfoxide. Both these compounds contain two methyl groups attached to the same atom of a functional group. The functional group in DMF is an amide group, while the functional group of DMSO is an oxide group.

CONTENTS

1. Overview and Key Difference
2. What is DMF 
3. What is DMSO
4. Side by Side Comparison – DMF vs DMSO in Tabular Form
5. Summary

What is DMF?

The term DMF stands for dimethyl formamide. It is an organic compound having the chemical formula (CH₃)₂NC(O)H. This substance occurs as a colourless liquid that is miscible with water and most other organic solvents. This liquid is also useful as a solvent for chemical reactions. This is due to its polar nature.

DMF is considered as an aprotic solvent with a high boiling point. Therefore, this solvent can facilitate SN2 reactions. DMF is usually odourless, but some grades of this liquid may have a fishy smell due to the presence of impurities such as dimethylamine. These impurities can be removed via sparging degraded samples of DMF with inert gas, e.g. argon gas, or via sonication of the samples under reduced pressure.

When considering the chemical structure of DMF, it has partial bond character in C-N and C-O bonds. This compound can get hydrolyzed in the presence of strong acids and bases at high temperatures. Furthermore, in the presence of sodium hydroxide, this compound converts into formate and dimethylamine. Moreover, DMF can undergo decarbonylation at temperatures near the boiling point of DMF, forming dimethylamine. Therefore, if we are conducting a distillation process using this liquid, it has to be performed at reduced pressures and low temperatures.

DMF can be produced via a combination of methyl formate with dimethylamine. Another method is to perform the reaction of dimethylamine with carbon monoxide. In addition, DMF can be prepared from supercritical carbon dioxide using ruthenium-based catalysts.

What is DMSO?

The term DMSO stands for dimethyl sulfoxide having the chemical formula (CH3)2SO. It occurs as a colourless liquid. This liquid is an important polar aprotic solvent that can dissolve both polar and nonpolar compounds. Also, this liquid is miscible with a wide range of organic solvents as well as with water. DMSO has a relatively high boiling point. Moreover, it has an unusual garlic-like taste in the mouth after contact with the skin.

When considering the structure of DMSO molecule, it has Cs symmetry and trigonal pyramidal molecular geometry. There is a non-bonded electron pair on the approximately tetrahedral sulfur atom. The chemical formula of DMSO is C2H6OS. It occurs as a colourless liquid.

In the industrial scale productions, DMSO is prepared from dimethyl sulfide, which is a byproduct of Kraft process. This process involves an oxidation reaction that occurs with either oxygen gas or nitrogen dioxide gas.

What is the Difference Between DMF and DMSO?

DMF is dimethyl formamide while DMSO is dimethyl sulfoxide. Both are organic compounds. The key difference between DMF and DMSO is that DMF is an amide, whereas DMSO is an organosulfur compound.

DMF is prepared by combining methyl formate and dimethylamine or from the reaction between dimethylamine and carbon monoxide while DMSO is prepared from dimethyl sulfide, which is a byproduct of Kraft process. Moreover, DMF is more toxic than DMSO.

Below infographic gives a more detailed side-by-side comparison of both to discern the differences between DMF and DMSO easily.

Summary – DMF vs DMSO

DMF is dimethyl formamide while DMSO is dimethyl sulfoxide. Both are organic compounds. The key difference between DMF and DMSO is that DMF is an amide, whereas DMSO is an organosulfur compound.

Reference:

1. Dimethyl sulfoxide. (2020, August 29). Retrieved September 05, 2020, Available here.

Image Courtesy:

1. “Dimethylformamide-2D-skeletal” By Sbrools – Own work (CC BY-SA 3.0) via Commons Wikimedia
2. “Dimethylsulfoxid” By NEUROtiker – Own work (Public Domain) via Commons Wikimedia