Chemical Properties
Gray powder
Physical properties
1,2,4-Benzenetriol forms colorless platelets or prisms that quickly colorize in air. It is soluble in water and polar solvents, and slightly soluble in chloroform and carbon disulfide.
Uses
1,2,4-Trihydroxybenzene is an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.It is used as a metabolite of benzene.
Definition
ChEBI: Benzene-1,2,4-triol is a benzenetriol carrying hydroxy groups at positions 1, 2 and 4. It has a role as a mouse metabolite.
Production Methods
1,2,4-Benzenetriol is synthesized by hydrolysis of 1,2,4-triacetoxybenzene, which is prepared by the acid-catalyzed
reaction of p-benzoquinone with acetic anhydride.
Other production methods for 1,2,4-Benzenetriol are oxidation of resorcinol with hydrogen peroxide and Dakin oxidation of 2,4- or
3,4-dihydroxybenzaldehydes or 2,4- or 3,4-dihydroxyacetophenones with alkaline hydrogen peroxide solution.
General Description
1,2,4-Benzenetriol is also known as hydroxyhydroquinone. It is an intermediary metabolite of benzene that is present in roasted coffee beans. It is mutagenic and it causes cleaving of DNA single strands by the generation of reactive oxygen species.
Chemical Reactivity
1,2,4-Benzenetriol is, like other phenols, a strong reducing
agent. Its basic aqueous solution absorbs gaseous
oxygen to produce black precipitates of the humic acid type. 1,2,4-Benzenetriol shows typical reactions of phenols. Derivatives of the
tautomeric keto form are also known: halogenation of hydroxyhydroquinone, for example, gives
1,2,5,5-tetrahalocyclohexene-3,4,6-trione. Condensation with ethylacetoacetate produces dihydroxycoumarin; reaction with phthalic anhydride
yields hydroxyhydroquinonephthalein. Monosubstitution of a hydroxy group by an amino
group occurs easily at room temperature and
gives 2,4-dihydroxyaniline.
Safety Profile
Poison by
subcutaneous and intraperitoneal routes.
Human mutation data reported. When
heated to decomposition it emits acrid
smoke and irritating fumes.
Purification Methods
Crystallise the triol from Et2O or Et2O/EtOH, and dry it in a vacuum. The picrate forms orange-red needles m 96o. [Beilstein 6 H 1087, 6 I 541, 6 II 1071, 6 III 6276.]
