Chemical Properties
3,4,5-Trimethoxyaniline is off-white to beige-brown, grey or pink powder
Uses
3,4,5-Trimethoxyaniline is a tri-substituted aniline derivative with sympatholytic activity. It is used in the preparation of a novel class of anticancer agents.
Application
[1] BANDANA SHARMA; Shweta P; Munish Kumar Yadav. MOLECULAR STRUCTURE, EXPERIMENTAL AND THEORETICAL (HF, DFT) SPECTRAL ANALYSIS OF 3,4,5- TRIMETHOXYANILINE[J]. Rasayan Journal of Chemistry, 2023. DOI:10.31788/rjc.2023.1628371.
[2] J. TSUNETSUGU; S. E; M SATO. ChemInform Abstract: TROPENYLATION, DETROPENYLATION AND SCHIFF BASE FORMATION IN THE REACTION OF 3,4,5-TRIMETHOXYANILINE WITH TROPENYLIUM ION[J]. ChemInform, 1975. DOI:10.1002/chin.197545221.
Application
3,4,5-Trimethoxyaniline can be used:
(1) As experimental studies, infrared spectra and laser Raman spectra of 3,4,5-trimethoxyaniline were investigated[1].
(2) Tropanilisation, detropanilisation and Schiff base formation in the reaction of 3,4,5-trimethoxyaniline with tropanilide ions as organic reaction reagents[2].
Synthesis
Step B / Intermediate B9: Synthesis of 3,4,5-trimethoxyaniline
To a solution of 1,2,3-trimethoxy-5-nitrobenzene (6.64 g, 31.2 mmol) in ethanol (250 mL) was added palladium carbon (10%, 300 mg) and hydrazine hydrate (85%, 5.7 mL). The reaction mixture was heated to reflux for 1 hour after gas release ceased. Upon completion of the reaction, the mixture was cooled to room temperature and the catalyst was removed by filtration followed by evaporation of the solvent to afford 3,4,5-trimethoxyaniline (5.5 g, 96.4% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 5.86 (s, 2H), 4.82 (br, 2H), 3.64 (s, 6H), 3.50 (s, 3H).
References
[1] Patent: WO2012/92880, 2012, A1. Location in patent: Page/Page column 60
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 9, p. 3414 - 3425
[3] Chemische Berichte, 1888, vol. 21, p. 615
[4] Australian Journal of Scientific Research, Series A: Physical Sciences, 1950, vol. 3, p. 467,500
[5] Journal of Pharmacy and Pharmacology, 1958, vol. 10, p. 47,59
