Methyl Ester Derivatives for GC-MS: Easy Room Temperature Dilute and Shoot Sample Preparation Using Hexane Solution of Trimethylsilyldiazomethane

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SAFETY NOTE:  Diazomethane and Trimethylsilyldiazomethane need to be handled properly like any alkylation reagents.  Proper caution should be taken in handling and using these compounds.  Here are links to information from Wikipedia:

Diazomethane_wikipedia

Trimethylsilyldiazomethane_wikipedia

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Trimethylsilyldiazomethane Derivitization Reactions:  A purchased mixture of trimethylsilyldiazomethane in hexane from Sigma Aldrich is a convenient method for preparing methyl esters of organic acids.  The reaction is performed at room temperature.  The details of the reaction and possible derivatization by-products are presented.

This material was a handout for a poster session at an ASMS conference.  The work was never formally published.  Diazomethane and Trimethylsilyldiazomethane reactions are often used to form methyl ester derivatives to increase the volatility and stability of organic compounds for gas chromatography mass spectrometry.   Normally the reactions give the desired derivatives. However, sometimes artifacts (by-products) are noted.

diazomethane

trimethylsilyldiazomethane_2

The handout linked below lists all the types of artifacts noted in our laboratory in the last 15 years and ones we have found in the literature.

diazomethane_trimethylsilyldiazomethane_reactions

General Review Article on Derivitization:

Derivatization Methods in GC and GC/MS

DOI: dx.doi.org/10.5772/intechopen.81954
Serban C. Moldoveanu1* and Victor David2

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