Chemical Properties
Beige to brown crystal powder
Uses
2-Amino-5-methylphenol was used in the synthesis of tridentate Schiff base ligand and novel non-metallocene catalysts with phenoxy-imine ligands.
General Description
2-Amino-5-methylphenol reacts with bovine hemoglobin to form 2-amino-4,4α-dihydro-4α-7-dimethyl-3
H-phenoxazine-3-one, which inhibits the proliferation of Poliovirus in Vero cells. It is converted to dihydrophenoxazinone by purified human hemoglobin.
Synthesis
The general procedure for the synthesis of 6-aminoresorcinol from 6-nitroresorcinol was as follows: 5-methyl-2-nitrophenol (1.0 g, 6.53 mmol) was dissolved in methanol (10 mL) at 23 °C, and Pd/C catalyst (10 wt%, 400 mg) was added. The reaction mixture was deoxygenated at low temperature, followed by replacement of air in the system with hydrogen (supplied via a balloon). After the reaction was stirred for 5 h under hydrogen atmosphere, the reaction mixture was filtered through a diatomaceous earth pad and the diatomaceous earth pad was washed with methanol (100 mL). Finally, the combined filtrates were concentrated under reduced pressure to afford 2-amino-5-methylphenol (801 mg, 100% yield).
Purification Methods
Crystallise it from H2O, 50% EtOH, or toluene. [Beilstein
References
[1] Patent: US2006/211603, 2006, A1. Location in patent: Page/Page column 69
[2] Advanced Synthesis and Catalysis, 2013, vol. 355, # 5, p. 907 - 911
[3] Journal of Heterocyclic Chemistry, 1982, vol. 19, # 6, p. 1545 - 1547
[4] Synthesis, 2001, # 1, p. 81 - 84
[5] Justus Liebigs Annalen der Chemie, 1902, vol. 322, p. 18
