93000-99-8

Usage

Physical state

Colorless, flammable liquid

Odor

Strong aromatic

Classification

Cycloalkene

Structure

Ring of carbon atoms with alternating single and double bonds

Stability

Unstable, not commonly found in pure form

Occurrence

Reactive intermediate in organic synthesis

Usage

Research and laboratory settings as a precursor for various organic compounds

Health and environmental hazards

Potential hazards, requires proper precautions during handling

Upstream product

• 22293-10-3 (1-diazoethyl)benzene 
• 698-20-4 1-(diazomethyl)-2-methylbenzene 
• 35745-45-0 o-tolylmethylene biradical 

Downstream Products

• 100-42-5 styrene 

Relevant academic research and scientific papers

Rearrangements of the Isomeric Tolylmethylenes

We present evidence for a mechanism in which the isomeric tolylmethylenes interconvert via methylcycloheptatetraene intermediates.Photolysis (>470 nm) of diazo compounds 1-4, matrix isolated in argon at 10 K, generates triplet tolylmethylenes 8-11.Photoly

Direct Spectroscopic Observation of Intramolecular Hydrogen Shifts in Carbenes

Triplet o-tolylmethylene (13a) decays thermally to singlet o-xylylene (14a) in an argon matrix at temperatures as low as 4.6 K.The thermal, intramolecular -hydrogen shift has been observed directly by IR and UV spectroscopy.The carbene disappearance kinetics follow the standard (time)1/2 dependence, due to multiple reaction sites in the matrix.The small temperature dependence and non-Arrhenius behavior of the rate implicate a tunneling mechanism.In contrast, triplet 1-phenylethylidene (17a) is thermally stable in argon or xenon matrices at 10 K.Warming 17a to 65 K in a xenon matrix produces styrene (18a).The intramolecular -hydrogen shift has been observed directly by IR spectroscopy.The carbene disappearance kinetics show apparent first-order behavior.We estimate an upper limit of ca. 4.7 kcal/mol for the singlet-triplet energy gap in 17a.