6-Amino-2-methylphenol

Chemical Properties

Appearance:Light yellow crystal powder

Uses

6-Amino-2-methylphenol is a colorant that has been classified as a skin sensitizer. It is used in the manufacture of inorganic pigments and other organic compounds, such as dyes and paints. 6-Amino-2-methylphenol absorbs ultraviolet radiation and reacts with chloride to form 2-amino, 6-(chloromethyl) phenol, which has been shown to have subchronic toxicity. This chemical also photodegrades in sunlight, producing free radicals that can damage cells.

Synthesis

B. 2-Methyl-6-nitrophenol (542 mg, 3.54 mmol), 10% Pd/C catalyst (54 mg) with EtOAc/EtOH mixed solvent (5.5 mL/11 mL) were placed in a reaction flask and the reaction was stirred overnight under a hydrogen atmosphere and at atmospheric pressure. Upon completion of the reaction, the reaction mixture was filtered through a pad of diatomaceous earth to remove the catalyst and the filtrate was subsequently concentrated under reduced pressure to afford 2-amino-6-methylphenol as a brown solid (373 mg, 85% yield).

References

[1] Journal of Organic Chemistry, 2015, vol. 80, # 23, p. 11734 - 11743
[2] Patent: WO2008/110793, 2008, A1. Location in patent: Page/Page column 104
[3] Patent: KR2018/117068, 2018, A. Location in patent: Paragraph 0084; 0625; 0628; 0634; 0635
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 23, p. 7974 - 7985
[5] Journal of the American Chemical Society, 2005, vol. 127, # 30, p. 10545 - 10559