Phenacetin

• Formula: C₁₀H₁₃NO₂
• Molecular weight: 179.2157
• IUPAC Standard InChI: InChI=1S/C10H13NO2/c1-3-13-10-6-4-9(5-7-10)11-8(2)12/h4-7H,3H2,1-2H3,(H,11,12) Copy

  
• IUPAC Standard InChIKey: CPJSUEIXXCENMM-UHFFFAOYSA-N Copy
• CAS Registry Number: 62-44-2
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Acetamide, N-(4-ethoxyphenyl)-; p-Acetophenetidide; p-Ethoxyacetanilide; Acetophenetidin; Acetophenetidine; Acetophenetin; Fenidina; Fenina; Kalmin; N-Acetyl-p-phenetidine; Pertonal; Phenacetine; Phenazetin; Phenedina; Phenidin; Phenin; 4-Ethoxyacetanilide; 4'-Ethoxyacetanilide; Phenacitin; p-Acetophenetide; p-Acetophenetidine; p-Acetphenetidin; p-Phenetidine, N-acetyl-; Acet-p-phenalide; Acet-p-phenetidin; Acetanilide, 4'-ethoxy-; Aceto-4-phenetidine; N-(4-Ethoxyphenyl)acetamide; Phenacet; Pyraphen; 1-Acetamido-4-ethoxybenzene; Aceto-para-phenalide; Aceto-para-phenetidide; para-Acetophenetidide; Acetphenetidin; Acetylphenetidin; Achrocidin; Anapac; APC; ASA COMPOUND; Bromo seltzer; Buff-A-comp; Citra-fort; Clistanol; Codempiral; Commotional; Contradol; Contradouleur; Coricidin; Coriforte; Coryban-D; Daprisal; Darvon compound; Dasikon; Dasin; Dasin CH; Dolostop; Dolviran; Edrisal; Empiral; Empirin compound; Emprazil; Emprazil-C; Epragen; p-Ethoxyanilid kyseliny octove; N-para-Ethoxyphenylacetamide; Fenacetin; Fenacetina; Fenia; Fiorinal; Fortacyl; Gelonida; Gewodin; Helvagit; Hjorton'S powder; Hocophen; KAFA; Malex; Melabon; Melaforte; Norgesic; Pamprin; Paracetophenetidin; Paramette; Paratodol; para-Phenacetin; Phenacetinum; Phenacon; Phenaphen; Phenaphen plus; Phenazetina; Phenodyne; Pyrroxate; Quadronal; RCRA Waste number U187; Robaxisal-PH; Salgydal; Sanalgine; Saridon; Seranex; Sinedal; Sinubid; Sinutab; Stellacyl; Super anahist; Synalgos-DC; Synalogos; Tacol; Terracydin; Tetracydin; Thephorin A-C; Treupel; Veganine; Viden; Wigraine; Xaril; Zactirin compound; p-Acetophenetitide; Para-acetphenetidin; Acetanilide, p-ethoxy-; 4-Ethoxy-acetanilid; 4-(Acetylamino)phenetole; N-Acetyl-4-ethoxyaniline; N-Acetyl-p-ethoxyaniline; P-A-C Compound (Salt/Mix); Phensal (Salt/Mix); Butigetic (Salt/Mix)
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • References
  • Notes
• Other data available:
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Enthalpy of vaporization

Enthalpy of sublimation

Enthalpy of fusion

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes

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

Lemoult, 1906
Lemoult, M.P., Thermochimie. - Chaleur de combustion et de formation de quelques composes cycliques azotes, Compt. Rend., 1906, 143, 772-775. [all data]

Manzo and Ahumanda, 1990
Manzo, R.H.; Ahumanda, A.A., Effects of solvent medium on solubility. V: Enthalpic and entropic contributions to the free energy changes of Di-substituted benzene derivatives in ethanol: Water and ethanol: Cyclohexane mixtures, J. Pharm. Sci., 1990, 79, 12, 1109, https://doi.org/10.1002/jps.2600791214 . [all data]

Khattab, 1983
Khattab, F.I., Thermochim. Acta, 1983, 61, 253-268. [all data]

Grady, Hays, et al., 1973
Grady, L.T.; Hays, S.E.; King, R.H.; Klein, H.R.; Mader, W.J.; Wyatt, D.K.; Zimmere, R.O., Drug purity profiles, J. Pharm. Sci., 1973, 62, 459. [all data]

Vecchio and Tomassetti, 2009
Vecchio, Stefano; Tomassetti, Mauro, Vapor pressures and standard molar enthalpies, entropies and Gibbs energies of sublimation of three 4-substituted acetanilide derivatives, Fluid Phase Equilibria, 2009, 279, 1, 64-72, https://doi.org/10.1016/j.fluid.2009.02.001 . [all data]

Wiedemann, 1972
Wiedemann, H.G., Applications of thermogravimetry for vapor pressure determination, Thermochim. Acta, 1972, 355-366. [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]

Peña, Escalera, et al., 2009
Peña, M.A.; Escalera, B.; Reíllo, A.; Sánchez, A.B.; Bustamante, P., Thermodynamics of cosolvent action: Phenacetin, salicylic acid and probenecid, J. Pharm. Sci., 2009, 98, 3, 1129-1135, https://doi.org/10.1002/jps.21497 . [all data]

Wassvik, Holmén, et al., 2006
Wassvik, Carola M.; Holmén, Anders G.; Bergström, Christel A.S.; Zamora, Ismael; Artursson, Per, Contribution of solid-state properties to the aqueous solubility of drugs, European Journal of Pharmaceutical Sciences, 2006, 29, 3-4, 294-305, https://doi.org/10.1016/j.ejps.2006.05.013 . [all data]

Wassvik, Holmén, et al., 2008
Wassvik, Carola M.; Holmén, Anders G.; Draheim, Rieke; Artursson, Per; Bergström, Christel A.S., Molecular Characteristics for Solid-State Limited Solubility, J. Med. Chem., 2008, 51, 10, 3035-3039, https://doi.org/10.1021/jm701587d . [all data]

Vecchio, Catalani, et al., 2004
Vecchio, Stefano; Catalani, Alessia; Rossi, Vanessa; Tomassetti, Mauro, Thermal analysis study on vaporization of some analgesics. Acetanilide and derivatives, Thermochimica Acta, 2004, 420, 1-2, 99-104, https://doi.org/10.1016/j.tca.2003.09.039 . [all data]

Manzo and Ahumada, 1990
Manzo, Ruben H.; Ahumada, Amelia A., Effects of solvent medium on solubility. V: Enthalpic and entropic contributions to the free energy changes of Di-substituted benzene derivatives in ethanol: Water and ethanol: Cyclohexane mixtures, J. Pharm. Sci., 1990, 79, 12, 1109-1115, https://doi.org/10.1002/jps.2600791214 . [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, References

• Symbols used in this document:
  

  Tfus	Fusion (melting) point
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization

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