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
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • 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

IR Spectrum

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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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

Mass spectrum (electron ionization)

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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

Spectrum

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Additional Data

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Lang (editor), 1963
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1963, 4, 67. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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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