|Jmol-3D images||Image 1|
|Molar mass||110.1 g/mol|
|Appearance||white to brown feathery crystals|
|Odor||faint, phenolic odor|
|Density||1.344 g/cm³, solid|
|Melting point||105 °C; 221 °F; 378 K|
|Boiling point||245.5 °C; 473.9 °F; 518.6 K (sublimes)|
|Solubility in water||43 g/100 mL|
|Solubility||very soluble in pyridine
soluble in chloroform, benzene, CCl4, ether, acetate
|Vapor pressure||20 Pa (20 °C)|
|Refractive index (nD)||1.604|
|EU classification||Harmful (Xn)|
|S-phrases||(S2), S22, S26, S37|
|Flash point||127 °C; 261 °F; 400 K|
|Autoignition temperature||510 °C; 950 °F; 783 K|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Catechol, also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C6H4(OH)2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts. It was first discovered by destructive distillation of the plant extract catechin. About 20 million kg are now synthetically produced annually as a basic organic chemical, mainly as a precursor to pesticides, flavors, and fragrances.
Catechol occurs as feathery white crystals that are very rapidly soluble in water.
(The name "catechol" has also been used as a chemical class name, where it refers generally to the catechins.)
Isolation and synthesis
Catechol was first isolated in 1839 by H. Reinsch by distilling it from the solid tannic preparation catechin, which is the residuum of catechu, the boiled or concentrated juice of Mimosa catechu (Acacia catechu L.f). Upon heating catechin above its decomposition point, a substance Reinsch first named "pyrocatechol" distilled and condensed as a white solid ("pyro" referring to heat). This was a thermal decomposition product of the flavanols in catechin. "Pyrocatechol" is now simply referred to as catechol.
- C6H5OH + H2O2 → C6H4(OH)2 + H2O
Previously, catechol was produced by 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 hydriodic acid.
Like other difunctional benzene derivatives, catechol readily condenses to form heterocyclic compounds. Cyclic esters are formed upon treatment with phosphorus trichloride and phosphorus oxychloride, carbonyl chloride, and sulphuryl chloride:
- C6H4(OH)2 + XCl2 → C6H4(O2X) + 2 HCl
- where X = CO, SO2, PCl, P(O)Cl
With metal ions
Catechol is the conjugate acid of a chelating agent used widely in coordination chemistry. Basic solutions of catechol react with iron(III) to give the red [Fe(C6H4O2)3]3-. Ferric chloride gives a green coloration with the aqueous solution, whilst the alkaline solution rapidly changes to a green and finally to a black color on exposure to the air. It reduces silver solutions in the cold and alkaline copper on heating. Catechol can also be conjugated to ruthenium. [RuIII(NH3)4(catechol)]+ oxidizes faster than catechol in the presence of oxygen, but controlled potential electrolysis showed that its oxidation involves only one electron.
Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase (also known as catecholase, or catechol oxidase). Upon mixing the enzyme with the substrate and exposure to oxygen (as when a potato or apple is cut and left out), the colorless catechol oxidizes to reddish-brown melanoid pigments, derivatives of benzoquinone. The enzyme is inactivated by adding an acid, such as lemon juice, and slowed with cooling. Excluding oxygen also prevents the browning reaction. Benzoquinone is said to be antimicrobial, which slows the spoilage of wounded fruits and other plant parts.
It is also a component of castoreum, a substance from castors, used in perfumery.
Presence of the catechol moiety
Catechol moieties are also found widely within the natural world. Arthropod cuticle consists of chitin linked by a catechol moiety to protein. The cuticle may be strengthened by cross-linking (tanning and sclerotization), in particular, in insects, and of course by biomineralization. Catechols such as DHSA are produced through the metabolism of cholesterol by bacteria such as Mycobacterium tuberculosis.
Urushiols are naturally existing organic compounds that have the catechol skeleton structure and diphenol functionality but with alkyl groups substituted onto the aromatic ring. Urushiols are the skin-irritating poisons found in plants like poison ivy, etc. Catecholamines are biochemically significant hormones/neurotransmitters that are phenethylamines in which the phenyl group has a catechol skeleton structure.
Approximately 50% of synthetic catechol is consumed in the production of pesticides, the remainder being used as a precursor to fine chemicals such as perfumes and pharmaceuticals. It is a common building block in organic synthesis. Several industrially significant flavors and fragrances are prepared starting from catechol. Guaiacol is prepared by methylation of catechol and is then converted to vanillin on a scale of about 10M kg per year (1990). The related monoethyl ether of catechol, guethol, is converted to ethylvanillin, a component of chocolate confectioneries. 3-Trans-Isocamphylcyclohexanol, widely used as a replacement for sandalwood oil, is prepared from catechol via guaiacol and camphor. Piperonal, a flowery scent, is prepared from the methylene diether of catechol followed by condensation with glyoxal and decarboxylation.
Catechol is used as a black-and-white photographic developer, but, except for some special purpose applications, its use until recently was largely historical. Modern catechol developing was pioneered by noted photographer Sandy King. His "PyroCat" formulation enjoys widespread popularity among modern black-and-white film photographers.
The catechol skeleton occurs in a variety of natural products such as urushiols, which are the skin-irritating poisons found in plants like poison ivy, and catecholamines, drugs imitating them (such as MDMA), hormones/neurotransmitters, and catechin, which is found in tea. Many pyrocatechin derivatives have been suggested for therapeutic applications.
The "preferred IUPAC name" (PIN) of catechol is benzene-1,2-diol.  The trivial name pyrocatechol is a retained IUPAC name, according to the 1993 Recommendations for the Nomenclature of Organic Chemistry.  
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- Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, 2005: Weinheim. Published online: 15 January 2003
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- IUPAC, Commission on Nomenclature of Organic Chemistry. A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993) R-18.104.22.168 Alcohols and phenols.
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