2835-99-6

Description

4-Amino-3-methylphenol is a metabolite of 3-methyl-4-nitrophenol. It is a major metabolite of carcinogenic o-toluidine and causes DNA damage in the presence of Cu(II).

Chemical Properties

Light gray powder

Uses

4-Amino-3-methylphenol is a useful reagent for the synthesis of piperidine (piperazine)-amide substituted derivatives as multi-target antipsychotics.4-Amino-3-methylphenol was used in synthesis of a new type of tweezer-molecule in which a strongly preferred binding conformation is generated by convergent, intramolecular hydrogen bonding.

Application

4-Amino-m-cresol is used as an oxidative hair dye at a maximum concentration of 1.5% after mixing with peroxide.

Definition

ChEBI: A substituted aniline in which the aniline ring carries 4-hydroxy and 6-methyl substituents; a urinary metabolite of lidocaine.

General Description

4-Amino-3-methylphenol is a metabolite of 3-methyl-4-nitrophenol. It is a major metabolite of carcinogenic o-toluidine and causes DNA damage in the presence of Cu(II).

Flammability and Explosibility

Notclassified

Synthesis

The synthesis of 4-Amino-3-methylphenol is as follows:A mixture of the para-benzoquinone mono-oxime (1.26 mmol),SnCl2 (0.72 g, 3.80 mmol), 20 mL of CH2Cl2, and 0.2 mL of concentrated HCl, was heated to reflux for 16 h. The CH2Cl2 was removed under reduced pressure, and the residue was dissolved in ethyl acetate and washed with concentrated aqueous NaHCO3. The organic layer was dried over anhydrous Na2SO4 and the filtrate was concentrated under reduced pressure to afford the solid product.

Purification Methods

Crystallise it from 50% EtOH. [Beilstein 13 H 593, 13 IV 1698.]