Pyrocatechol

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Pyrocatechol
Pyrocatechol
IUPAC name Pyrocatechol
Other names catechol
benzene-1,2-diol
2-hydroxyphenol
α-hydroxyphenol
o-benzenediol
o-hydroxyphenol
1,2-dihydroxybenzene
pyrocatechin
Identifiers
CAS number [120-80-9]
RTECS number UX1050000
SMILES Oc1c(O)cccc1
Properties
Molecular formula C6H6O2
Molar mass 110.1 g/mol
Appearance white solid
Density 1.344 g/cm³, solid
Melting point

105 °C, 378 K, 221 °F
Boiling point

245.5 °C, 519 K, 474 °F
Solubility in water 43 g/100 mL
Hazards
EU classification Harmful (Xn)
NFPA 704
1
2
0
 
R-phrases R21/22, R36/38
S-phrases (S2), S22, S26, S37
Flash point 127 °C
Related compounds
Related benzenediols Resorcinol
Hydroquinone
Related compounds 1,2-benzoquinone
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Pyrocatechol, more commonly known as catechol, is a benzenediol, with the formula C6H4(OH)2. It is a commonly used building block in organic synthesis.

Contents

[edit] Isolation and synthesis

Catechol was first isolated in 1839 by H. Reinsch by distilling catechin (the juice of Mimosa catechu (Acacia catechu L.f))[citation needed]; it occurs free in kino and in beechwood tar; its sulfonic acid is present in the urine of horse and humans.

Catechol can be prepared by fusing 2-phenolsulfonic acid, 2-chlorphenol, 2-bromophenol, or 2,6-phenoldisulfonic acid with potash, or, better, by heating its methyl ether, guaiacol, a constituent of beechwood tar, with hydriodic acid.[citation needed] Many pyrocatechin derivatives have been suggested for therapeutic applications.

[edit] Reactions

[edit] Organic chemistry

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.

Catechols produce quinones with the addition of Ceric ammonium nitrate (CAN).

[edit] 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.[citation needed] It reduces silver solutions in the cold and alkaline copper on heating.[citation needed] 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 (Almeida et al., 2007).

[edit] Occurrence

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, hormones/neurotransmitters, and catechin, which is found in tea.

Small amounts of catechol occur naturally in fruits and vegetables, along with the enzyme polyphenol oxidase. Upon mixing the enzyme with the substrate and exposure to oxygen (as when a potato or apple is cut), the colorless catechol oxidizes to reddish-brown benzoquinone derivatives. The enzyme is inactivated by adding an acid, such as lemon juice, or by refrigeration. Excluding oxygen also prevents the browning reaction. Benzoquinone is said to be antimicrobial, which slows the spoilage of wounded fruits and other plant parts.

[edit] Uses

Pyrocatechol was used as a developing agent in black-and-white photographic developers, but except for some special purpose applications, its use is largely historical.

[edit] Nomenclature

Pyrocatechol is the name recommended by the International Union of Pure and Applied Chemistry (IUPAC) in its 1993 Recommendations for the Nomenclature of Organic Chemistry.[1]

[edit] References

  • Almeida, W. L. C.; Vitor, D. N.; Pereira, M. R. G; de Sá, D. S.; Alvarez, L. D. G.; Pinheiro, A. M.; Costa, S. L.; Costa, M. F. D.; Rocha, Z. N.; El-Bachá, R. S. Redox properties of ruthenium complex with catechol are involved in toxicity to glial cells. J. Chil. Chem. Soc. 52 (3): 1240-1243, 2007.
  • Barner, B. A. "Catechol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.

[edit] See also

[edit] References

 This article does not cite any references or sources. (September 2007)
Please help improve this article by adding citations to reliable sources. Unverifiable material may be challenged and removed.
  1. ^ Panico, R.; & Powell, W. H. (Eds.) (1994). A Guide to IUPAC Nomenclature of Organic Compounds 1993. Oxford: Blackwell Science. ISBN 0-632-03488-2. 

[edit] External links

This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.