Toluene

• Formula: C₇H₈
• Molecular weight: 92.1384
• IUPAC Standard InChI: InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3 Copy

  
• IUPAC Standard InChIKey: YXFVVABEGXRONW-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-88-3
• 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.
• Isotopologues:
  • Toluene-D3
  • Toluene-D8
• Other names: Benzene, methyl; Methacide; Methylbenzene; Methylbenzol; Phenylmethane; Antisal 1a; Toluol; Methane, phenyl-; NCI-C07272; Tolueen; Toluen; Toluolo; Rcra waste number U220; Tolu-sol; UN 1294; Dracyl; Monomethyl benzene; CP 25; NSC 406333; methylbenzene (toluene)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • UV/Visible spectrum
  • Gas Chromatography
  • Fluid Properties
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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

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:
DRB - Donald R. Burgess, Jr.
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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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

C₇H₇^- +  =

By formula: C₇H₇^- + H⁺ = C₇H₈

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₇H₈ = (C₃H₉Si⁺ • C₇H₈)

Free energy of reaction

 +  = ( • )

By formula: Br^- + C₇H₈ = (Br^- • C₇H₈)

Free energy of reaction

C₄H₉⁺ +  = (C₄H₉⁺ • )

By formula: C₄H₉⁺ + C₇H₈ = (C₄H₉⁺ • C₇H₈)

C₇H₈⁺ +  = (C₇H₈⁺ • )

By formula: C₇H₈⁺ + C₇H₈ = (C₇H₈⁺ • C₇H₈)

Bond type: Charge transfer bond (positive ion)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₇H₈ = (C₆H₇N⁺ • C₇H₈)

Bond type: Charge transfer bond (positive ion)

C₉H₁₂⁺ +  = (C₉H₁₂⁺ • )

By formula: C₉H₁₂⁺ + C₇H₈ = (C₉H₁₂⁺ • C₇H₈)

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

By formula: NO^- + C₇H₈ = (NO^- • C₇H₈)

 +  =  + 

By formula: HBr + C₇H₇Br = C₇H₈ + Br₂

 +  = ( • )

By formula: Cl^- + C₇H₈ = (Cl^- • C₇H₈)

Free energy of reaction

 +  =  + 

By formula: HI + C₇H₇I = C₇H₈ + I₂

 + 0.5 =  + 0.5

By formula: C₇H₇Br + 0.5H₂ = C₇H₈ + 0.5Br₂

 +  = ( • )

By formula: I^- + C₇H₈ = (I^- • C₇H₈)

=

By formula: C₇H₈ = C₇H₈

=  + 0.5

By formula: C₇H₇I = C₇H₈ + 0.5I₂

( • ) +  = ( • 2)

By formula: (Li⁺ • C₇H₈) + C₇H₈ = (Li⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (Na⁺ • C₇H₈) + C₇H₈ = (Na⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (Cs⁺ • C₇H₈) + C₇H₈ = (Cs⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (Rb⁺ • C₇H₈) + C₇H₈ = (Rb⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (K⁺ • C₇H₈) + C₇H₈ = (K⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (Cr⁺ • C₇H₈) + C₇H₈ = (Cr⁺ • 2C₇H₈)

 +  =  + 

By formula: C₁₀H₁₄ + C₆H₆ = C₇H₈ + C₉H₁₂

 +  = ( • )

By formula: Li⁺ + C₇H₈ = (Li⁺ • C₇H₈)

 +  = ( • )

By formula: Na⁺ + C₇H₈ = (Na⁺ • C₇H₈)

 +  = ( • )

By formula: Cs⁺ + C₇H₈ = (Cs⁺ • C₇H₈)

 +  = ( • )

By formula: Rb⁺ + C₇H₈ = (Rb⁺ • C₇H₈)

 +  = ( • )

By formula: K⁺ + C₇H₈ = (K⁺ • C₇H₈)

 +  = ( • )

By formula: Cr⁺ + C₇H₈ = (Cr⁺ • C₇H₈)

IR Spectrum

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

Data compiled by: Coblentz Society, Inc.

• GAS (20 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution
• LIQUID; PERKIN-ELMER; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 3800-1330 AND 10% IN CS2 FOR 1330-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

• liquid; Bruker Tensor 27 FTIR; 0.48212986 cm^-1 resolution

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

• gas

Data compiled by: Pamela M. Chu, Franklin R. Guenther, George C. Rhoderick, and Walter J. Lafferty

• gas; IFS66V (Bruker); 3-Term B-H Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Boxcar Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Happ Genzel Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); NB Strong Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Triangular Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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

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, IR Spectrum, Mass spectrum (electron ionization), Notes

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

Roux, Temprado, et al., 2008
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Draeger, 1985
Draeger, J.A., The methylbenzenes II. Fundamental vibrational shifts, statistical thermodynamic functions, and properties of formation, J. Chem. Thermodyn., 1985, 17, 263-275. [all data]

Chao J., 1984
Chao J., Chemical thermodynamic properties of toluene, o-, m- and p-xylenes, Thermochim. Acta, 1984, 72, 323-334. [all data]

Pitzer K.S., 1943
Pitzer K.S., The thermodynamics and molecular structure of benzene and its methyl derivatives, J. Am. Chem. Soc., 1943, 65, 803-829. [all data]

Taylor W.J., 1946
Taylor W.J., Heats, equilibrium constants, and free energies of formation of the alkylbenzenes, J. Res. Nat. Bur. Stand., 1946, 37, 95-122. [all data]

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Scott D.W., Toluene: thermodynamic properties, molecular vibrations, and internal rotation, J. Phys. Chem., 1962, 66, 911-914. [all data]

Montgomery J.B., 1942
Montgomery J.B., The heat capacity of organic vapors. IV. Benzene, fluorobenzene, toluene, cyclohexane, methylcyclohexane and cyclohexene, J. Am. Chem. Soc., 1942, 64, 2375-2377. [all data]

Scott, Guthrie, et al., 1962
Scott, D.W.; Guthrie, G.B.; Messerly, J.F.; Todd, S.S.; Berg, W.T.; Hossenlopp, I.A.; McCullough, J.P., Toluene: thermodynamic properties, molecular vibrations, and internal rotation, J. Phys. Chem., 1962, 66, 911-914. [all data]

Kelley, 1929
Kelley, K.K., The heat capacity of toluene from 14K to 298K. The entropy and the free energy of formation, J. Am. Chem. Soc., 1929, 51, 2738-2741. [all data]

Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E., Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide, J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]

Shiohama, Ogawa, et al., 1988
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Reddy, 1986
Reddy, K.S., Isentropic compressibilities of binary liquid mixtures at 303.15 and 313.15 K, J. Chem. Eng. Data, 1986, 31, 238-240. [all data]

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Tardajos, Aicart, et al., 1986
Tardajos, G.; Aicart, E.; Costas, M.; Patterson, D., Liquid structure and second-order mixing functions for benzene, toluene, and p-xylene with n-alkanes, J. Chem. Soc., Faraday Trans., 1986, 1 82, 2977-2987. [all data]

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Stephens, M.; Olson, J.D., Measurement of excess heat capacities by differential scanning calorimetry, Thermochim. Acta, 1984, 76, 79-85. [all data]

Grolier, Inglese, et al., 1982
Grolier, J.-P.E.; Inglese, A.; Wilhelm, E., Excess volumes and excess heat capacities of tetrachloroethene + cyclohexane, + methylcyclohexane, + benzene, and + toluene at 298.15 K, J. Chem. Thermodynam., 1982, 14, 523-529. [all data]

Wilhelm, Faradjzadeh, et al., 1982
Wilhelm, E.; Faradjzadeh, A.; Grolier, J.-P.E., Excess volumes and excess heat capacities of 2,3-dimethylbutane + butane and + toluene, J. Chem. Thermodynam., 1982, 14, 1199-1200. [all data]

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Andolenko and Grigor'ev, 1979
Andolenko, R.A.; Grigor'ev, B.A., Investigation of isobaric heat capacity of aromatic hydrocarbons at atmospheric pressure, Iaz. Vyssh. Ucheb. Zaved., Neft i Gaz (11), 1979, 78, 90. [all data]

Fortier and Benson, 1979
Fortier, J.-L.; Benson, G.C., Heat capacities of some binary aromatic hydrocarbon mixtures containing benzene or toluene, J. Chem. Eng. Data, 1979, 24(1), 34-37. [all data]

Fortier and Benson, 1977
Fortier, J.-L.; Benson, G.C., Excess heat capacities of binary mixtures of tetrachloromethane witlh some aromatic liquids at 298.15 K, J. Chem. Thermodynam., 1977, 9, 1181-1188. [all data]

Wilhelm, Grolier, et al., 1977
Wilhelm, E.; Grolier, J.-P.E.; Karbalai Ghassemi, M.H., Molar heat capacities of binary liquid mixtures: 1,2-dichloroethane + benzene, + toluene, and + p-xylene, Ber. Bunsenges. Phys. Chem., 1977, 81, 925-930. [all data]

Fortier and Benson, 1976
Fortier, J.-L.; Benson, G.C., Excess heat capacities of binary liquid mixtures determined with a Picker flow calorimeter, J. Chem. Thermodynam., 1976, 8, 411-423. [all data]

Holzhauer and Ziegler, 1975
Holzhauer, J.K.; Ziegler, W.T., Temperature dependence of excess thermodynamic properties of n-heptane-toluene, methylcyclohexane-toluene, and n-heptane-methylcyclohexane systems, J. Phys. Chem., 1975, 79(6), 590-604. [all data]

Pedersen, Kay, et al., 1975
Pedersen, M.J.; Kay, W.B.; Hershey, H.C., Excess enthalpies, heat capacities, and excess heat capacities as a function of temperature in liquid mixtures of ethanol + toluene, ethanol + hexamethyldisiloxane, and hexamethyldisiloxane + toluene, J. Chem. Thermodynam., 1975, 7, 1107-1118. [all data]

Rajagopal and Subrahmanyam, 1974
Rajagopal, E.; Subrahmanyam, S.V., Excess function of VE,(dVE/dp)T, and CpE of isooctane + benzene and + toluene, J. Chem. Thermodynam., 1974, 6, 873-876. [all data]

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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]

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Hwa, S.C.P.; Ziegler, W.T., Temperature dependence of excess thermodynamic properties of ethanol-methylcyclohexane and ethanol-toluene systems, J. Phys. Chem., 1966, 70(8), 2572-2593. [all data]

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Burlew, 1940
Burlew, J.S., Measurement of the heat capacity of a small volume of liquid by the piezo-thermometric method. III. Heat capacity of benzene and of toluene from 8°C. to the boiling point, J. Am. Chem. Soc., 1940, 62, 696-700. [all data]

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Vold, R.D., A calorimetric test of the solubility equation for regular solutions, J. Am. Chem. Soc., 1937, 59, 1515-1521. [all data]

Aoyama and Kanda, 1935
Aoyama, S.; Kanda, E., Studies on the heat capacities at low temperature. Report I. Heat capacities of some organic substances at low temperature, Sci. Rept. Tohoku Imp. Univ. [1]24, 1935, 107-115. [all data]

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Scott, D.W.; Guthrie, G.B.; Messerly, J.F.; Todd, S.S.; Berg, W.T.; Hossenlopp, I.A.; McCullough, J.P., Toluene: Thermodynamic Propoerties, Molecular Vibrations, and Internal Rotation, J. Phys. Chem., 1962, 66, 911-4. [all data]

Ziegler and Andrews, 1942
Ziegler, W.T.; Andrews, D.H., The heat capacity of benzene-d6, J. Am. Chem. Soc., 1942, 64, 2482. [all data]

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Stull, D.R., A Semi-micro Calorimeter for Measuring Heat Capacities at Low Temp., J. Am. Chem. Soc., 1937, 59, 2726. [all data]

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Chirico and Steele, 1994
Chirico, R.D.; Steele, W.V., Reconciliation of Calorimetrically and Spectroscopically Derived Methyl Benzene. The Importance of the Third Virial Coefficient, Ind. Eng. Chem. Res., 1994, 33, 157-67. [all data]

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Goodwin, R.D., Toluene thermophysical properties from 178 to 800 K at pressures to 1000 Bar, J. Phys. Chem. Ref. Data, 1989, 18, 1565-636. [all data]

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Simon, M., Methods and Apparatus Used at the Bureau of Physicochemical Standards XV. Critical Constants and Straight-Line Diameters of Ten Hydrocarbons, Bull. Soc. Chim. Belg., 1957, 66, 375-81. [all data]

Lenchitz and Velicky, 1970
Lenchitz, Charles; Velicky, Rodolf W., Vapor pressure and heat of sublimation of three nitrotoluenes, J. Chem. Eng. Data, 1970, 15, 3, 401-403, https://doi.org/10.1021/je60046a022 . [all data]

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Lee and Holder, 1993
Lee, Chang Ha; Holder, Gerald D., Vapor-liquid equilibria in the systems toluene/naphthalene and cyclohexane/naphthalene, J. Chem. Eng. Data, 1993, 38, 2, 320-323, https://doi.org/10.1021/je00010a034 . [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]

Forziati, Norris, et al., 1949
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Notes

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• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  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
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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