Furfural

• Formula: C₅H₄O₂
• Molecular weight: 96.0841
• IUPAC Standard InChI: InChI=1S/C5H4O2/c6-4-5-2-1-3-7-5/h1-4H Copy

  
• IUPAC Standard InChIKey: HYBBIBNJHNGZAN-UHFFFAOYSA-N Copy
• CAS Registry Number: 98-01-1
• 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.
• Species with the same structure:
  • 2-Furancarbaldehyde
• Other names: 2-Furancarboxaldehyde; 2-Furaldehyde; α-Furole; Artificial ant oil; Fural; Furaldehyde; Furale; Furancarbonal; Furfuraldehyde; Furfurole; Furfurylaldehyde; Furole; Pyromucic aldehyde; 2-Formylfuran; 2-Furanaldehyde; 2-Furancarbonal; 2-Furfural; 2-Furfuraldehyde; 2-Furylaldehyde; Furol; 2-Furylmethanal; Artificial oil of ants; Furfurale; Furfurol; NCI-C56177; 2-Furil-metanale; 2-Furankarbaldehyd; Rcra waste number U125; 2-Furylcarboxaldehyde; Qo furfural; Furan-2-aldehyde; Furan-2-carbaldehyde; NSC 8841; 2-furancarboxyaldehyde; furfural (2-furancarboxaldehyde); 2-Furancarboxaldehyde (furfural); furancarboxaldehyde (furfural)
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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 liquid

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

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 fusion

Entropy of fusion

Reaction 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

 +  =  + 

By formula: C₁₁H₁₀N₂O + H₂O = C₆H₈N₂ + C₅H₄O₂

Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 4000-1330 CM^-1, 10% IN CS2 FOR 1330-600 CM^-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• VAPOR (5 MICROLITER AT 150 C); PERKIN-ELMER 180; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2-3 CM^-1 cm^-1 resolution

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

• gas

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, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics 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.

Avramescu and Isagescu, 1978
Avramescu, F.; Isagescu, D.A., Heats of combustion of mono- and difurfurylidene acetone, Rev. Roum. Chim., 1978, 23, 655-659. [all data]

Kudchadker and Kudchadker, 1975
Kudchadker, S.A.; Kudchadker, A.P., Thermodynamic properties of oxygen compounds. III. Benzaldehyde and furfural (2-furaldehyde), Ber. Bunsenges. Phys. Chem., 1975, 12, 432-437. [all data]

Miller, 1936
Miller, P., The free energy of furfural and some of its derivatives, Iowa State Coll. J. Sci., 1936, 10, 91-93. [all data]

Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R., Etude thermochimique dans la serie furanique, Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]

Kudchadker S.A., 1975
Kudchadker S.A., Thermodynamic properties of oxygen compounds. III. Benzaldehyde and furfural (2-furaldehyde), Thermochim. Acta, 1975, 12, 432-437. [all data]

Miller, 1935
Miller, P., The free energy of furfural and some of its derivatives, Iowa State Coll. J. Sci., 1935, 10, 91-93. [all data]

Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A., Study of the heat capacity of selected solvents, Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]

Omel'chenko, 1962
Omel'chenko, F.S., Specific heat of furfural, Izv. Vyssh. Ucheb. Zaved. Pishch. Tekhnol., 1962, No. 2, 151-152. [all data]

von Reis, 1881
von Reis, M.A., Die specifische Wärme flüssiger organischer Verbindungen und ihre Beziehung zu deren Moleculargewicht, Ann. Physik [3], 1881, 13, 447-464. [all data]

Timmermans, 1922
Timmermans, J., Investigation of the Freezing Point of Organic Substances VII, Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]

Miller, 1936, 2
Miller, P., The Free Energy of Furfural and Some of Its Derivatives, Iowa State Coll. J. Sci., 1936, 10, 91-3. [all data]

Emel'yanenko, Dabrowska, et al., 2007
Emel'yanenko, Vladimir N.; Dabrowska, Aldona; Hertel, Marcus O.; Scheuren, Hans; Sommer, Karl, Vapor Pressures, Enthalpies of Vaporization, and Limiting Activity Coefficients in Water at 100 °C of 2-Furanaldehyde, Benzaldehyde, Phenylethanal, and 2-Phenylethanol, J. Chem. Eng. Data, 2007, 52, 2, 468-471, https://doi.org/10.1021/je060406c . [all data]

Hauschild, Wu, et al., 1987
Hauschild, Torsten; Wu, Huey S.; Sandler, Stanley I., Vapor-liquid equilibrium of the mixtures 2-furaldehyde/1-butanol and 2-furaldehyde/4-methyl-2-pentanone, J. Chem. Eng. Data, 1987, 32, 2, 226-229, https://doi.org/10.1021/je00048a028 . [all data]

Mathews, 1926
Mathews, J.H., The accurate measurement of heats of vaporization of liquids, J. Am. Chem. Soc., 1926, 48, 562-576. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [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]

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]

Matthews, Sumner, et al., 1950
Matthews, J.B.; Sumner, J.F.; Moelwyn-Hughes, E.A., The vapour pressures of certain liquids, Trans. Faraday Soc., 1950, 46, 797, https://doi.org/10.1039/tf9504600797 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Evans and Aylesworth, 1926
Evans, W.V.; Aylesworth, M.B., Some critical constants of furfural, Ind. Eng. Chem., 1926, 18, 1, 24-27, https://doi.org/10.1021/ie50193a013 . [all data]

Matthews, Sumner, et al., 1950, 2
Matthews, J.B.; Sumner, J.F.; Moelwyn-Hughes, E.A., The Vapour Pressures of Certain Liquids, Trans. Faraday Soc., 1950, 46, 797-803, https://doi.org/10.1039/tf9504600797 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Landrieu, 1905
Landrieu, M.Ph., Thermochimie. - Thermochimie des hydrazones, Compt. Rend., 1905, 141, 358-361. [all data]

Klapstein, MacPherson, et al., 1990
Klapstein, D.; MacPherson, C.D.; O'Brien, R.T., The photoelectron spectra and electronic structure of 2-carbonyl furans, Can. J. Chem., 1990, 68, 747. [all data]

Linda, Marino, et al., 1971
Linda, P.; Marino, G.; Pignataro, S., A comparison of sensitivities to substituent effects of five- membered heteroaromatic rings in gas phase ionization, J. Chem. Soc. B, 1971, 1585. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Grammaticakis, 1953
Grammaticakis, P., Contribution a l'etude de l'absorption dans l'U.-V. moyen et le visible de quelques aldehydes et cetones aromatiques ainsi que de certains de leurs derives fonctionnels, (Premier memoire), Bull. Soc. Chim. Fr., 1953, 20, 821-826. [all data]

Notes

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

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrH°	Enthalpy of reaction 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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