Benzoic acid, 4-hydroxy-

• Formula: C₇H₆O₃
• Molecular weight: 138.1207
• IUPAC Standard InChI: InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) Copy

  
• IUPAC Standard InChIKey: FJKROLUGYXJWQN-UHFFFAOYSA-N Copy
• CAS Registry Number: 99-96-7
• 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: Benzoic acid, p-hydroxy-; p-Hydroxybenzoic acid; p-Salicylic acid; Paraben-acid; 4-Carboxyphenol; 4-Hydroxybenzoic acid; para-Hydroxybenzoic acid; Hydroxybenzoic acid, para; Kyselina 4-hydroxybenzoova; NSC 4961; Paraben
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• Information on this page:
  • Phase change data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
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  • Gas Phase Kinetics Database
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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:
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.

Enthalpy of sublimation

Enthalpy of fusion

References

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

Armstrong, James, et al., 1979
Armstrong, N.A.; James, K.C.; Wong, C.K., Inter-relationships between solubilities, distribution coefficients and melting points of some substituted benzoic and phenylacetic acids, J. Pharm. Pharmacol., 1979, 31, 1, 627, https://doi.org/10.1111/j.2042-7158.1979.tb13606.x . [all data]

Herbert, 1967
Herbert, A.J., Transition temperatures and transition energies of the p-n-alkoxy benzoic acids, from n-propyl to n-octadecyl, Trans. Faraday Soc., 1967, 63, 555, https://doi.org/10.1039/tf9676300555 . [all data]

Davies and Jones, 1954
Davies, M.; Jones, J.I., The sublimation pressures and heats of sublimation of some carboxylic acids, Trans. Faraday Soc., 1954, 50, 1042. [all data]

King, McWhirter, et al., 1945
King, L.C.; McWhirter, M.; Barton, D.M., Reactions of Acetophenols with Iodine and Pyridine and the Preparation of Hydroxybenzoic Acids, J. Am. Chem. Soc., 1945, 67, 2089-92. [all data]

Pinto, Diogo, et al., 2005
Pinto, Susana S.; Diogo, Hermínio P.; Guedes, Rita C.; Costa Cabral, Benedito J.; Minas da Piedade, Manuel E.; Martinho Simões, José A., Energetics of Hydroxybenzoic Acids and of the Corresponding Carboxyphenoxyl Radicals. Intramolecular Hydrogen Bonding in 2-Hydroxybenzoic Acid, J. Phys. Chem. A, 2005, 109, 42, 9700-9708, https://doi.org/10.1021/jp054220g . [all data]

Sabbah and Le, 1993
Sabbah, R.; Le, T.H.D., Etude thermodynamique des trois isomeres de l'acide bydroxybenzolque, Can. J. Chem., 1993, 71, 1378-1383. [all data]

Jones, 1960
Jones, A.H., Sublimation Pressure Data for Organic Compounds., J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019 . [all data]

ARMSTRONG, JAMES, et al., 2011
ARMSTRONG, N.A.; JAMES, K.C.; WONG, C.K., Inter-relationships between solubilities, distribution coefficients and melting points of some substituted benzoic and phenylacetic acids, Journal of Pharmacy and Pharmacology, 2011, 31, 1, 627-631, https://doi.org/10.1111/j.2042-7158.1979.tb13606.x . [all data]

Nordström and Rasmuson, 2006
Nordström, Fredrik L.; Rasmuson, Åke C., Phase equilibria and thermodynamics ofp-hydroxybenzoic acid, J. Pharm. Sci., 2006, 95, 4, 748-760, https://doi.org/10.1002/jps.20569 . [all data]

Gracin and Rasmuson, 2002
Gracin, Sandra; Rasmuson, Åke C., Solubility of Phenylacetic Acid, p -Hydroxyphenylacetic Acid, p -Aminophenylacetic Acid, p -Hydroxybenzoic Acid, and Ibuprofen in Pure Solvents, J. Chem. Eng. Data, 2002, 47, 6, 1379-1383, https://doi.org/10.1021/je0255170 . [all data]

Heath, Singh, et al., 1992
Heath, E.A.; Singh, P.; Ebisuzaki, Y., Structure of p-hydroxybenzoic acid and p-hydroxybenzoic acid-acetone complex (2/1), Acta Crystallogr Sect C Cryst Struct Commun, 1992, 48, 11, 1960-1965, https://doi.org/10.1107/S0108270192002361 . [all data]

Notes

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• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions

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