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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).
Hazard Statements: H227-H302-H315-H319-H335
Combustible liquid. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P235-P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep cool. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant