Benzene, 1,3-dimethyl-

• Formula: C₈H₁₀
• Molecular weight: 106.1650
• IUPAC Standard InChI: InChI=1S/C8H10/c1-7-4-3-5-8(2)6-7/h3-6H,1-2H3 Copy

  
• IUPAC Standard InChIKey: IVSZLXZYQVIEFR-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-38-3
• 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.
• Other names: m-Xylene; m-Dimethylbenzene; m-Xylol; 1,3-Dimethylbenzene; 1,3-Xylene; 2,4-Xylene; m-Methyltoluene; meta-Xylene; NSC 61769; UN 1307; 1,3-dimethylbenzene (m-xylene)
• 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
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • 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)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

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

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
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

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

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

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

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
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Reaction thermochemistry data

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

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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess

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

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₈H₁₀ = (C₃H₉Si⁺ • C₈H₁₀)

Free energy of reaction

C₉H₁₂⁺ +  = (C₉H₁₂⁺ • )

By formula: C₉H₁₂⁺ + C₈H₁₀ = (C₉H₁₂⁺ • C₈H₁₀)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₈H₉^- +  =

By formula: C₈H₉^- + H⁺ = C₈H₁₀

 +  = ( • )

By formula: Cl^- + C₈H₁₀ = (Cl^- • C₈H₁₀)

Free energy of reaction

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.

• LIQUID (NEAT); PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• VAPOR (0.5 MICROLITER AT 150 C); NICOLET FTIR; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 CM^-1 cm^-1 resolution
• VAPOR (30 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); PERKIN-ELMER 180; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 CM^-1 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

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

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.

Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heats of combustion and formation at 25°C of the alkylbenzenes through C₁₀H₁₄, and of the higher normal monoalkylbenzenes, J. Res. NBS, 1946, 36, 455-461. [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]

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]

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]

Hastings S.H., 1957
Hastings S.H., Thermodynamic properties of selected methylbenzenes from 0 to 1000 K, J. Phys. Chem., 1957, 61, 730-735. [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]

Coops, Mulder, et al., 1946
Coops, J.; Mulder, D.; Dienske, J.W.; Smittenberg, J., The heats of combustion of a number of hydrocarbons, Rec. Trav. Chim. Pays/Bas, 1946, 65, 128. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Richards and Barry, 1915
Richards, T.W.; Barry, F., The heats of combustion of aromatic hydrocarbons and hexamethylene, J. Am. Chem. Soc., 1915, 37, 993-1020. [all data]

Richards and Jesse, 1910
Richards, T.W.; Jesse, R.H., Jr., The heats of combustion of the octanes and xylenes, J. Am. Chem. Soc., 1910, 32, 268-298. [all data]

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

Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-1558. [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]

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]

Swietoslawski and Zielenkiewicz, 1958
Swietoslawski, W.; Zielenkiewicz, A., Mean specific heats of binary positive azeotropes, Bull. Acad. Pol. Sci. Ser. Sci. Chim., 1958, 6, 367-369. [all data]

Kurbatov, 1947
Kurbatov, V.Ya., Specific heat of liquids. I. Specific heat of benzenoid hydrocarbons, Zhur. Obshch. Khim., 1947, 17, 1999-2003. [all data]

Willams and Daniels, 1924
Willams, J.W.; Daniels, F., The specific heats of certain organic liquids at elevated temperatures, J. Am. Chem. Soc., 1924, 46, 903-917. [all data]

Huffman, Parks, et al., 1930, 2
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal Data on Organic Compounds: VII The Heat Capacities, Entropies and Free Energies of Twelve Aromatic Hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-58. [all data]

Tsonopoulos and Ambrose, 1995
Tsonopoulos, C.; Ambrose, D., Vapor-Liquid Critical Properties of Elements and Compounds. 3. Aromatic Hydrocarbons, J. Chem. Eng. Data, 1995, 40, 547-558. [all data]

Ambrose, 1987
Ambrose, D., Vapor Pressures of Some Aromatic Hydrocarbons, J. Chem. Thermodyn., 1987, 19, 1007. [all data]

Ambrose, Broderick, et al., 1967
Ambrose, D.; Broderick, B.E.; Townsend, R., The Vapour Pressures above the Normal Boiling Point and the Critical Pressures of Some Aromatic Hydrocarbons, J. Chem. Soc. , 1967, 1967, 1967, 633-41. [all data]

Glaser and Ruland, 1957
Glaser, F.; Ruland, H., Untersuchungsen über dampfdruckkurven und kritische daten einiger technisch wichtiger organischer substanzen, Chem. Ing. Techn., 1957, 29, 772. [all data]

Altschul, 1893
Altschul, M., The critical values of some organic compounds, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1893, 11, 577. [all data]

Akhundov and Asadullaeva, 1968
Akhundov, T.S.; Asadullaeva, N.N., Specific volumes of m-xylene near the critical point, Izv. Vyssh. Uchebn. Zaved., Neft Gaz, 1968, 11, 6, 836. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Swiatek and Malanowski, 2002
Swiatek, Barbara E.; Malanowski, Stanislaw K., Vapor-Liquid Equilibrium in m -Xylene + Cyclohexanol at 19.99 and 94.93 kPa, J. Chem. Eng. Data, 2002, 47, 3, 478-481, https://doi.org/10.1021/je010246z . [all data]

Park and Gmehling, 1989
Park, So Jin; Gmehling, Juergen, Isobaric vapor-liquid equilibrium data for the binary systems 1,3,5-trimethylbenzene/N-formylmorpholine and m-xylene/N-formylmorpholine, J. Chem. Eng. Data, 1989, 34, 4, 399-401, https://doi.org/10.1021/je00058a008 . [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]

Willingham, Taylor, et al., 1945
Willingham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor pressures and boiling points of some paraffin, alkylcyclopentane, alkylcyclohexane, and alkylbenzene hydrocarbons, J. RES. NATL. BUR. STAN., 1945, 35, 3, 219-17, https://doi.org/10.6028/jres.035.009 . [all data]

Forziati, Norris, et al., 1949
Forziati, Alphonse F.; Norris, William R.; Rossini, Frederick D., Vapor pressures and boiling points of sixty API-NBS hydrocarbons, J. RES. NATL. BUR. STAN., 1949, 43, 6, 555-17, https://doi.org/10.6028/jres.043.050 . [all data]

Machat, 1983
Machat, V., , Thesis, Utzcht, Prague, 1983. [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]

Williamham, Taylor, et al., 1945
Williamham, C.B.; Taylor, W.J.; Pignocco, J.M.; Rossini, F.D., Vapor Pressures and Boiling Points of Some Paraffin, Alkylcyclopentane, Alkylcyclohexane, and Alkylbenzene Hydrocarbons, J. Res. Natl. Bur. Stand. (U.S.), 1945, 35, 3, 219-244, https://doi.org/10.6028/jres.035.009 . [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]

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [all data]

Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H., Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies, J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034 . [all data]

Caldwell and Bartmess
Caldwell, G.; Bartmess, J.E., , Unpublished results. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Notes

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

• 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°gas	Entropy of gas at standard conditions
  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
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  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
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.