1,3-Benzodioxole (1,2-methylenedioxybenzene) is an organic compound with the formula C6H4O2CH2. The compound is classified as benzene derivative and a heterocyclic compound containing the methylenedioxy functional group. It is a colorless liquid.
Although benzodioxole is not particularly important, many related compounds containing the methylenedioxyphenyl group are bioactive, and thus are found in pesticides and pharmaceuticals.[1]
Preparation
1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.[2][3]
See also
- 1,4-Benzodioxine
- MDMA
- Methylenedioxy
- Safrole
- Piperonal
- Piperonyl butoxide and sesamex are benzodioxole-based adjuvants, used to enhance the efficacy of some insecticides[4]
References
- ^ Murray, M., “Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation”, Curr. Drug Metab. 2000, volume 1, 67-84. doi:10.2174/1389200003339270
- ^ Bonthrone, W. & Cornforth, J. (1969). “The methylenation of catechols”. Journal of the Chemical Society (9): 1202–1204. doi:10.1039/J39690001202. Retrieved 28 December 2013.
- ^ Fujita, Harushige; Yamashita & Masataro (1973). “The Methylenation of Several Allylbenzene-1,2-diol Derivatives in Aprotic Polar Solvents”. Bulletin of the Chemical Society of Japan. 46 (11): 3553–3554. doi:10.1246/bcsj.46.3553. Archived from the original on 10 May 2023. Retrieved 27 December 2013.
- ^ Metcalf Deceased, Robert L.; Horowitz, Abraham Rami (2014). “Insect Control, 2. Individual Insecticides”. Ullmann’s Encyclopedia of Industrial Chemistry. pp. 1–94. doi:10.1002/14356007.s14_s01. ISBN 978-3-527-30673-2.