1,2-Benzenediol
- Formula: C6H6O2
- Molecular weight: 110.1106
- IUPAC Standard InChIKey: YCIMNLLNPGFGHC-UHFFFAOYSA-N
- 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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Phase change data
Go To: Top, Gas phase ion energetics 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:
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 518.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 513. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 518.8 | K | N/A | Krupatkin and Rozhentsova, 1971 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tboil | 519.05 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 377. ± 1. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 377.5 | K | N/A | Andrews, Lynn, et al., 1926 | Uncertainty assigned by TRC = 0.2 K; obtained from cooling curve in absence of air; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 71.9 ± 0.8 | kJ/mol | GS | Verevkin and Kozlova, 2008 | Based on data from 378. to 389. K.; AC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 86. ± 4. | kJ/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
63.1 | 410. | A | Stephenson and Malanowski, 1987 | Based on data from 395. to 519. K.; AC |
61.2 | 393. | GC | Kundel, Lille, et al., 1975 | Based on data from 378. to 439. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
391.7 to 518.7 | 5.5033 | 2713.153 | -23.96 | von Terres, Gebert, et al., 1955 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
80.0 ± 0.5 | 302. | N/A | Chen, Oja, et al., 2006 | Based on data from 295. to 310. K.; AC |
81. ± 2. | 309. | V | Wolf and Weghofer, 1938 | ALS |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
22.000 | 376.85 | N/A | Bret-Dibat and Lichanot, 1989 | DH |
22.87 | 377.6 | N/A | Verevkin and Kozlova, 2008 | AC |
18.55 | 377.6 | N/A | Verevkin and Schick, 2000 | AC |
22.54 | 377.7 | DSC | Lee, Chang, et al., 1997 | AC |
22.01 | 376.9 | N/A | Bret-Dibat and Lichanot, 1989 | AC |
22.760 | 337.5 | N/A | Andrews, Lynn, et al., 1926, 2 | DH |
22.76 | 377.5 | C | Andrews, Lynn, et al., 1926, 2 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
58. | 376.85 | Bret-Dibat and Lichanot, 1989 | DH |
60.3 | 337.5 | Andrews, Lynn, et al., 1926, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
View reactions leading to C6H6O2+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.15 | PE | Palmer, Moyes, et al., 1979 | LLK |
8.56 | PE | Palmer, Moyes, et al., 1979 | Vertical value; LLK |
De-protonation reactions
C6H5O2- + =
By formula: C6H5O2- + H+ = C6H6O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1420. ± 8.8 | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 1422. ± 11. | kJ/mol | G+TS | Kebarle and McMahon, 1977 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1392. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 1393. ± 8.4 | kJ/mol | IMRE | Kebarle and McMahon, 1977 | gas phase; B |
Gas Chromatography
Go To: Top, Phase change data, Gas phase ion energetics data, References, Notes
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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1197. | da Silva, Borba, et al., 1999 | 30. m/0.25 mm/0.25 μm, H2, 4. K/min; Tstart: 50. C; Tend: 290. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | LM-5 | 1199.8 | Ré-Poppi and Santiago-Silva, 2005 | 30. m/0.25 mm/0.25 μm, He; Program: 60C(2min) => 15C/min => 180C => 5C/min => 280C (10min) |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Apieson L | 140. | 1215. | Hedin, Minyard, et al., 1967 | Nitrogen, Chromosorb W HMDS (60-80 mesh); Column length: 1.8 m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-5 MS | 1219. | Jerkovic and Marijanovic, 2010 | 30. m/0.25 mm/0.25 μm, Helium, 70. C @ 2. min, 3. K/min, 200. C @ 18. min |
Capillary | ZB-5 | 1210. | Harrison and Priest, 2009 | 30. m/0.25 mm/0.25 μm, Helium, 40. C @ 1. min, 6. K/min, 280. C @ 9. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1197. | Yusuf and Bewaji, 2011 | Helium; Column length: 30. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | ZB-5 | 1201. | de Simon, Estruelas, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 45 0C 3 0C/min -> 230 0C (10 min) 10 0C/min -> 270 0C (21 min) |
Normal alkane RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 2661. | Moon and Shibamoto, 2010 | 60. m/0.25 mm/0.50 μm, Helium, 40. C @ 5. min, 2. K/min, 210. C @ 70. min |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 2657. | de Simon, Estruelas, et al., 2009 | 30. m/0.25 mm/0.25 μm, Helium; Program: 45 0C 3 0C/min -> 230 0C (10 min) 10 0C/min -> 270 0C (21 min) |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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
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]
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]
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]
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, 1274-1287. [all data]
Palmer, Moyes, et al., 1979
Palmer, M.H.; Moyes, W.; Speirs, M.; Ridyard, J.N.A.,
The electronic structure of substituted benzenes; ab initio calculations and photoelectron spectra for phenol, the methyl- and fluoro-derivatives, and the dihydroxybenzenes,
J. Mol. Struct., 1979, 52, 293. [all data]
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B.,
Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria,
J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032
. [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,
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. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions 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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