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o-tolualdehyde was used in determination of alkenal-2,4-dinitrophenylhydrazones by HPLC by addition of phosphoric acid. It produces to give a single diastereomer of the tetrahydronaphthalene derivative under UV irradiation.
Shigehisa Uchiyama; Erika Matsushima; Shohei Aoyagi; Masanori Ando. Measurement of acid-catalyzed isomerization of unsaturated aldehyde-2,4-dinitrophenylhydrazone derivatives by high-performance liquid chromatography analysis. Analytica Chimica Acta. 2004, 523 157-163.
Grainne M Clifford; Aurélie Hadj-Aïssa; Robert M Healy; Abdelwahid Mellouki; Amalia Muñoz; Klaus Wirtz; Montserrat Martín Reviejo; Esther Borrás; John C Wenger. The atmospheric photolysis of o-tolualdehyde. Environmental Science & Technology. 2011, 45 (22), 9649-9657.
Under u.v. irradiation, o-tolualdehyde generates exclusively the (E)-dienol form which may be trapped by cycloaddition with the acrylate (or fumarate) ester of methyl lactate, to give a single diastereomer of the tetrahydronaphthalene derivative: Can. J. Chem., 67, 574 (1989):
The imine with t-butylamine undergoes lateral lithiation with LDA at the o-methyl group; see, e.g.: J. Org. Chem., 59, 2616 (1994).
Gefahrenhinweise (EU): H227-H301-H315-H319-H335
Combustible liquid. Toxic if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Avoid breathing dust/fume/gas/mist/vapours/spray. IF SWALLOWED: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.