Chemical Properties
pink crystal power
Uses
2,4,6-Trimethoxybenzaldehyde was used in the preparation and characterization of three RNA-specific fluorescent probes and their use in live cell imaging. It was used as starting reagent for the regioselective synthesis of new (+/-)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins.
General Description
2,4,6-Trimethoxybenzaldehyde exhibits significant anti-candida activity.
Synthesis
The reaction system was cooled to -5 to 0 °C under nitrogen protection using 1,3,5-trimethoxybenzene (40 g, 0.22 mol) and N,N-dimethylformamide. Subsequently, phosphoryl chloride (48 g, 0.5 mol) was slowly added dropwise over 30 to 45 minutes. After the dropwise addition was completed, the reaction mixture was kept at 0 °C and stirring was continued for 1 hour. Upon completion of the reaction, the mixture was poured onto crushed ice and neutralized with saturated sodium carbonate solution. The precipitate precipitated was collected by filtration and washed with distilled water to give the final 2,4,6-trimethoxybenzaldehyde. Yield: 46 g (98% yield); 1H NMR (CDCl3): δ 10.35 (s, 1H), 6.67 (s, 2H), 3.88 (s, 6H), 3.87 (s, 3H); Mass Spectrum (MS): m/e 197 (M + 1).
References
[1] Journal of Chemical Research, Miniprint, 1991, # 9, p. 2401 - 2413
[2] Patent: WO2011/121505, 2011, A1. Location in patent: Page/Page column 42
[3] European Journal of Organic Chemistry, 2015, vol. 2015, # 28, p. 6359 - 6369
[4] Patent: US2017/182051, 2017, A1. Location in patent: Paragraph 0122
[5] Journal of Chemical Research, 2015, vol. 39, # 8, p. 458 - 461
