1,2-Benzenediol

• Formula: C₆H₆O₂
• Molecular weight: 110.1106
• IUPAC Standard InChI: InChI=1S/C6H6O2/c7-5-3-1-2-4-6(5)8/h1-4,7-8H Copy

  
• IUPAC Standard InChIKey: YCIMNLLNPGFGHC-UHFFFAOYSA-N Copy
• CAS Registry Number: 120-80-9
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Pyrocatechol; o-Benzenediol; o-Dihydroxybenzene; o-Dioxybenzene; o-Hydroxyphenol; o-Phenylenediol; c.i. Oxidation base 26; c.i. 76500; Catechol; Catechol (phenol); Durafur developer c; Fouramine pch; Fourrine 68; Oxyphenic acid; Pelagol grey c; Phthalhydroquinone; Pyrocatechin; Pyrocatechine; 1,2-Dihydroxybenzene; 2-Hydroxyphenol; o-Hydroquinone; Benzene, o-dihydroxy-; NCI-C55856; o-Diphenol; Katechol; Pyrokatechin; Pyrokatechol; Kachin; 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2R-trans)-; NSC 1573; 1,2-Benzenediol (pyrocatechol); o-catecol
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Henry's Law data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Sabbah and Buluku, 1991
Sabbah, R.; Buluku, E.N.L.E., Thermodynamic study of three isomers of dihydroxybenzene, Can. J. Chem., 1991, 69, 481-488. [all data]

Ribeiro Da Silva and Ribeiro Da Silva, 1984
Ribeiro Da Silva, M.D.M.C.; Ribeiro Da Silva, M.A.V., Enthalpies of combustion of 1,2-dihydroxybenzene and of six alkylsubstituted 1,2-dihydroxybenzenes, J. Chem. Thermodyn., 1984, 16, 1149-1155. [all data]

Finch, Gardner, et al., 1983
Finch, A.; Gardner, P.J.; Wu, D., Studies on nitrophenols. Part IV. The standard enthalpies of combustion and formation of 1,2-dihydroxybenzene, 1,2- and 1,4-nitrophenol, Thermochim. Acta, 1983, 66, 333-342. [all data]

Pushin, 1954
Pushin, N.A., Heats of combustion and heats of formation of isomeric organic compounds, Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]

Kudchadker S.A., 1979
Kudchadker S.A., Ideal gas thermodynamic properties of benzene diols: pyrocatechol, resorcinol, and hydroquinone, Thermochim. Acta, 1979, 30, 319-326. [all data]

Barker, 1925
Barker, M.F., Calorific value and constitution, J. Phys. Chem., 1925, 29, 1345-1363. [all data]

Bret-Dibat and Lichanot, 1989
Bret-Dibat, P.; Lichanot, A., Thermodynamic properties of positional isomers of disubstituted benzene in condensed phase, Thermochim. Acta, 1989, 147(2), 261-271. [all data]

Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J., Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme, Z. Natursforsch. 5a, 1950, 101-108. [all data]

Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T., The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (3), Sci., Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 238-245. [all data]

Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J., The heat capacities and heat of crystallization of some isomeric aromatic compounds, J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]

Andrews, 1926
Andrews, D.H., The specific heats of some isomers of the type ortho, meta and para C6H4XY from 110 to 340K, J. Am. Chem. Soc., 1926, 48, 1287-1298. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Krupatkin and Rozhentsova, 1971
Krupatkin, I.L.; Rozhentsova, E.P., Some properties of systems with latent liquid immiscibility, Russ. J. Phys. Chem. (Engl. Transl.), 1971, 45, 1700. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Andrews, Lynn, et al., 1926, 2
Andrews, D.H.; Lynn, G.; Johnston, J., The Heat Capacities and Heat of Crystallization of Some Isomeric Aromatic Compounds, J. Am. Chem. Soc., 1926, 48, 1274. [all data]

Verevkin and Kozlova, 2008
Verevkin, Sergey P.; Kozlova, Svetlana A., Di-hydroxybenzenes: Catechol, resorcinol, and hydroquinone, Thermochimica Acta, 2008, 471, 1-2, 33-42, https://doi.org/10.1016/j.tca.2008.02.016 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Kundel, Lille, et al., 1975
Kundel, H.; Lille, U.; Kaidas, N., Tr. Tallin. Politekh. Inst., 1975, 390, 107. [all data]

von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten, Brennst.-Chem., 1955, 36, 272-274. [all data]

Chen, Oja, et al., 2006
Chen, Xu; Oja, Vahur; Chan, W. Geoffrey; Hajaligol, Mohammad R., Vapor Pressure Characterization of Several Phenolics and Polyhydric Compounds by Knudsen Effusion Method, J. Chem. Eng. Data, 2006, 51, 2, 386-391, https://doi.org/10.1021/je050293h . [all data]

Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H., Uber sublimationswarmen, Z. Phys. Chem., 1938, 39, 194-208. [all data]

Verevkin and Schick, 2000
Verevkin, Sergey P.; Schick, Christoph, Substituent Effects on the Benzene Ring. Determination of the Intramolecular Interactions of Substituents in tert -Alkyl-Substituted Catechols from Thermochemical Measurements, J. Chem. Eng. Data, 2000, 45, 5, 946-952, https://doi.org/10.1021/je0001126 . [all data]

Lee, Chang, et al., 1997
Lee, Ming-Jer; Chang, Yao-Kun; Lin, Ho-mu; Chen, Chang-Hsin, Solid-Liquid Equilibria for 4-Methoxyphenol with Catechol, Ethylenediamine, or Piperazine, J. Chem. Eng. Data, 1997, 42, 2, 349-352, https://doi.org/10.1021/je960201b . [all data]

da Silva, Borba, et al., 1999
da Silva, U.F.; Borba, E.L.; Semir, J.; Marsaioli, A.J., A simple solid injection device for the analyses of Bulbophyllum (Orchidaceae) volatiles, Phytochemistry, 1999, 50, 1, 31-34, https://doi.org/10.1016/S0031-9422(98)00459-2 . [all data]

Ré-Poppi and Santiago-Silva, 2005
Ré-Poppi, N.; Santiago-Silva, M., Polycyclic aromatic hydrocarbons and other selected organic compounds in ambient air of Campo Grande City, Brazil, Atmos. Environ., 2005, 39, 16, 2839-2850, https://doi.org/10.1016/j.atmosenv.2004.10.006 . [all data]

Hedin, Minyard, et al., 1967
Hedin, P.A.; Minyard, J.P.; Thompson, A.C., Chromatographic and spectral analysis of phenolic acids and related compounds, J. Chromatogr., 1967, 30, 43-53, https://doi.org/10.1016/S0021-9673(00)84111-4 . [all data]

Jerkovic and Marijanovic, 2010
Jerkovic, I.; Marijanovic, Z., Oak (Quercus frainetto Ten.) honeydaw honey - approach to screening of volatile organic composition and antioxidant capacity (DPPH and FRAP assay), Molecules, 2010, 15, 5, 3744-3756, https://doi.org/10.3390/molecules15053744 . [all data]

Harrison and Priest, 2009
Harrison, B.M.; Priest, F.G., Composition of peaks used in the preparation of malt for Scotch Whisky production - influence of geographical source and extraction depth, J. Agric. Food Chem., 2009, 57, 6, 2385-2391, https://doi.org/10.1021/jf803556y . [all data]

Yusuf and Bewaji, 2011
Yusuf, O.K.; Bewaji, C.O., GC-MS of volatile components of fermented wheat germ extract, J. Cereals Oilseeds, 2011, 2, 3, 38-42. [all data]

de Simon, Estruelas, et al., 2009
de Simon, B.F.; Estruelas, E.; Munoz, A.M.; Cadahia, E.; Sanz, M., Volatile compounds in acacia, chestnut, cherry, ash, and oak woods, with a view to their use in cooperage, J. Agric. Food Chem., 2009, 57, 8, 3217-3227, https://doi.org/10.1021/jf803463h . [all data]

Moon and Shibamoto, 2010
Moon, J.-K.; Shibamoto, T., Formation of volatile chemicals from thermal degradation of less volatile cofee components: quinic acid, caffeic acid, and chlorogenic acid, J. Agric. Food Chem., 2010, 58, 9, 5465-5470, https://doi.org/10.1021/jf1005148 . [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,solid	Constant pressure heat capacity of solid
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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