R-N=N=N (azide), R-N=N-R (azo); R2CN2 R = Ph, tms, CF3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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.[4] Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.[5]
^ICSC 1256 – DIAZOMETHANE
^ abcNIOSH Pocket Guide to Chemical Hazards. "#0182". National Institute for Occupational Safety and Health (NIOSH).
^"Diazomethane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^Proctor, Lee D.; Warr, Antony J. (November 2002). "Development of a Continuous Process for the Industrial Generation of Diazomethane". Organic Process Research & Development. 6 (6): 884–892. doi:10.1021/op020049k.
^Shioiri, Takayuki; Aoyama, Toyohiko; Snowden, Timothy (2001). "Trimethylsilyldiazomethane". Encyclopedia of Reagents for Organic Synthesis. e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt298.pub2. ISBN 0471936235.
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...
structural formula R2C=N+=N−. The simplest example of a diazo compound is diazomethane, CH2N2. Diazo compounds (R2C=N2) should not be confused with azo compounds...
source of CH2 group. Its behavior is akin to the less convenient reagent diazomethane. Trimethylsilyldiazomethane can be prepared by treating (trimethylsilyl)methylmagnesium...
diethyl ether). Dimethyl sulfate is intermediate in electrophilicity. Diazomethane is a popular methylating agent in the laboratory, but it is too hazardous...
powerful (and more dangerous) methylating reagents include methyl triflate, diazomethane, and methyl fluorosulfonate (magic methyl). These reagents all react...
von Pechmann, who prepared it by accident in 1898 while investigating diazomethane. When his colleagues Eugen Bamberger and Friedrich Tschirner characterized...
Migratory aptitudes of functional groups dictate rearrangement products. Diazomethane also produces ring enlargement, and its reaction is mechanistically similar...
believed to be an intermediate in the methylation of carboxylic acids by diazomethane, a common transformation. Loss of N2 is both enthalpically and entropically...
Carboxylic acids can be esterified using diazomethane: RCO2H + CH2N2 → RCO2CH3 + N2 Using this diazomethane, mixtures of carboxylic acids can be converted...
where an acid is converted into acyl halide, which is then reacted with diazomethane to give one additional methylene in the aliphatic chain. Many acids undergo...
abscheiden; … " (It should be mentioned that from an ether solution of diazomethane, upon standing, sometimes small quantities of a white, flakey substance...
generate an alkylidene carbene a ketone can be exposed to trimethylsilyl diazomethane and then a strong base. The two classes of carbenes are singlet and triplet...
diphenyldiazomethane to generate polycyclic phosphirane species. The diazomethane species must be highly conjugated to ensure the formation of the three...
chloride into a haloketone with diazomethane. It is an insertion reaction in that the methylene group from the diazomethane is inserted into the carbon-chlorine...
precursor to diazomethane, which is toxic and unstable. Diazald has become the favored commercially available precursor for the synthesis of diazomethane, compared...
being reacted sequentially with triethylamine, ethyl chloroformate, and diazomethane to produce the α-diazoketone, which is then reacted with silver trifluoroacetate...
reaction with ethyl propionate ester; the product of this then reacts with diazomethane to form an enol ether, which reacts with free guanidine in a second condensation...
the rats' bodies. In organic chemistry, MNNG is used as a source of diazomethane when reacted with aqueous potassium hydroxide. MNNG is a probable human...
been reported to be a comparatively safe and stable in situ source of diazomethane in organic synthesis.[citation needed] In particular, use as a methylating...
Hans von Pechmann in 1898, pyrazole was synthesized from acetylene and diazomethane. Pyrazoles react with potassium borohydride to form a class of ligands...
– 19 April 1902) was a German chemist, renowned for his discovery of diazomethane in 1894. Pechmann condensation and Pechmann pyrazole synthesis. He also...
abscheiden; ... (It should be mentioned that from an ether solution of diazomethane, upon standing, sometimes small quantities of a white, flakey substance...
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