Catechol

About 20,000 tonnes of catechol are now synthetically produced annually as a commodity organic chemical, mainly as a precursor to pesticides, flavors, and fragrances.

[5] Upon heating catechin above its decomposition point, a substance that Reinsch first named Brenz-Katechusäure (burned catechu acid) sublimated as a white efflorescence.

In 1841, both Wackenroder and Zwenger independently rediscovered catechol; in reporting on their findings, Philosophical Magazine coined the name pyrocatechin.

[2] It can be produced by reaction of salicylaldehyde with base and hydrogen peroxide (Dakin oxidation),[10] as well as the hydrolysis of 2-substituted phenols, especially 2-chlorophenol, with hot aqueous solutions containing alkali metal hydroxides.

Its methyl ether derivative, guaiacol, converts to catechol via hydrolysis of the CH3−O bond as promoted by hydroiodic acid (HI).

[13] The redox series catecholate dianion, monoanionic semiquinonate, and benzoquinone are collectively called dioxolenes.

Approximately 50% of the synthetic catechol is consumed in the production of pesticides, the remainder being used as a precursor to fine chemicals such as perfumes and pharmaceuticals.

The related monoethyl ether of catechol, guethol, is converted to ethylvanillin, a component of chocolate confectioneries.

Piperonal, a flowery scent, is prepared from the methylene diether of catechol followed by condensation with glyoxal and decarboxylation.

[20] Josef Maria Eder published in 1879 his findings on the use of catechol as a black-and-white photographic developer,[21][22] but, except for some special purpose applications, its use is largely historical.

Skeletal formula
Pyrocatechol
Ball-and-stick model
Ball-and-stick model
NFPA 704 four-colored diamond Health 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gas Flammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oil Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code