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diazomethane
Sign in to saveAlso known as Azimethylene, Azomethylene, Diazirine, acomethylene, EINECS 206-382-7, diazonium methylide
Diazomethane is an organic chemical compound with the formula CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomet
Chemical data
- Formula
- CH2N2
- Molecular weight
- 42.04 g/mol
- IUPAC name
- diazomethane
- SMILES
- C=[N+]=[N-]
- InChIKey
- YXHKONLOYHBTNS-UHFFFAOYSA-N
- XLogP
- 1.6
- Polar surface area
- 2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,568 papers- Diazomethane Pneumonia.Journal of occupational medicine. : official publication of the Industrial Medical Association · 1968
- Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations.Angewandte Chemie (International ed. in English) · 2020
- Lab-scale production of anhydrous diazomethane using membrane separation technology.Nature protocols · 2017
- THE REACTIONS OF DIAZOMETHANE WITH HETEROCYCLIC COMPOUNDS.Advances in heterocyclic chemistry · 1963
- Diazomethane as the active agent in nitrosoguanidine mutagenesis and lethality.Molecular & general genetics : MGG · 1968
via PubMed
Wikidata facts
- Mass
- 42.022
Show 11 more facts
- NIOSH Pocket Guide ID
- 0182
- chemical formula
- CH₂N₂
- immediately dangerous to life or health
- 3.44
- melting point
- -145
- boiling point
- -23
- vapor pressure
- 1
- ionization energy
- 9.00
- time-weighted average exposure limit
- 0.4
- canonical SMILES
- C=[N+]=[N-]
- Commons category
- Diazomethane
- electric dipole moment
- 1.50
via Wikidata · CC0
~7 min read
Article
10 sectionsContents
- Use
- Preparation
- Laboratory scale
- Industrial use
- Analysis
- Related compounds
- Safety
- Isomers
- References
- External links
Diazomethane is an organic chemical compound with the formula CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.
==Use== For safety and convenience diazomethane is always prepared as needed as a solution in ether and used as such. It converts carboxylic acids to methyl esters and phenols into their methyl ethers. The reaction is thought to proceed via proton transfer from carboxylic acid to diazomethane to give a methyldiazonium cation, which reacts with the carboxylate ion to give the methyl ester and nitrogen gas. Labeling studies indicate that the initial proton transfer is faster than the methyl transfer step. Since proton transfer is required for the reaction to proceed, this reaction is selective for the more acidic carboxylic acids (pKa ~ 5) and phenols (pKa ~ 10) over aliphatic alcohols (pKa ~ 15). center|frameless|500x500px