Uses
Used to prepare dyes. Industrially used in natural gas and refinery process streams. They also are used in polymer industry as monomers. Amines find use as additives for lubricating oils, engine fuels, and asphalt, and are producers of ethanolamines.
Synthesis
General procedure for the synthesis of 5-(4-aminophenyl)-2H-tetrazole from 5-(4-nitrophenyl)-1H-tetrazole: 5-(4-nitrophenyl)-1H-tetrazole (5.3 g, 27.7 mmol), anhydrous ethanol (50 mL), ethyl acetate (50 mL), and 10% palladium-carbon-caprolactone catalyst (500 mg) were added to an autoclave reactor, and reacted under hydrogen atmosphere ( 30 psi) for 16 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filter cake was washed with ethyl acetate. The filtrate was concentrated under reduced pressure to afford 4-(1H-tetrazol-5-yl)aniline as a light orange solid (4.5 g, 100% yield).
References
[1] Patent: WO2006/15158, 2006, A1. Location in patent: Page/Page column 38
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7392 - 7416
[3] Patent: WO2012/135641, 2012, A2. Location in patent: Page/Page column 67
[4] Patent: US6043254, 2000, A
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1981, vol. 17, # 11, p. 1142 - 1144
