4-Amino-3-methylphenol

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: 4-hydroxy-6-methylaniline is a substituted aniline in which the aniline ring carries 4-hydroxy and 6-methyl substituents; a urinary metabolite of lidocaine. It has a role as a drug metabolite. It is a member of phenols and a substituted aniline.

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

Not classified

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.]