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SAFETY NOTE: Diazomethane is a dangerous chemical. Extreme caution should be taken in handling and using this compound. Here is information on safety from Wikipedia:
“Diazomethane is toxic by inhalation or by contact with the skin or eyes (TLV 0.2ppm). Symptoms include chest discomfort, headache, weakness and, in severe cases, collapse. Symptoms may be delayed. Deaths from diazomethane poisoning have been reported. In one instance a laboratory worker consumed a hamburger near a fumehood where he was generating a large quantity of diazomethane, and died four days later from fulminating pneumonia. Like any other alkylating agent it is expected to be carcinogenic, but such concerns are overshadowed by its serious acute toxicity.”
“CH2N2 may explode in contact with sharp edges, such as ground-glass joints, even scratches in glassware. Glassware should be inspected before use and preparation should take place behind a blast shield. Specialized kits to prepare diazomethane with flame-polished joints are commercially available. The compound explodes when heated beyond 100 °C.”
http://en.wikipedia.org/wiki/Diazomethane
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This post summarizes artficats (reaction by-products) noted in our laboratory. It was a handout for an ASMS poster session from a conference. Diazomethane and Trimethylsilyldiazomethane reactions are often employed to increase the volatility and stability of organic acids for gas chromatography mass spectrometry. Normally the reactions give the desired methyl ester derivatives. However, sometimes artifacts (by-products are noted.
The paper 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. Also, convenient methods for producing small amounts of diazomethane and for utilizing both reagents are described.
http://www.littledomain.com/james/files/diazoalkanes.pdf
