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Phenol, 3-methyl-

Data at NIST subscription sites:

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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
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Quantity Value Units Method Reference Comment
Deltafgas-31.94 ± 0.26kcal/molCcbCox, 1961ALS
Deltafgas-31.63 ± 0.26kcal/molCcbAndon, Biddiscombe, et al., 1960ALS
Deltafgas-28.04kcal/molN/APushin, 1954Value computed using «DELTA»fHliquid° value of -177.0 kj/mol from Pushin, 1954 and «DELTA»vapH° value of 59.7 kj/mol from Cox, 1961.; DRB
Deltafgas-31.98kcal/molN/ABadoche, 1941Value computed using «DELTA»fHliquid° value of -193.5 kj/mol from Badoche, 1941 and «DELTA»vapH° value of 59.7 kj/mol from Cox, 1961.; DRB

Constant pressure heat capacity of gas

Cp,gas (cal/mol*K) Temperature (K) Reference Comment
9.24750.Kudchadker S.A., 1978Selected entropies and heat capacities are in close agreement with statistical values calculated by [ Green J.H.S., 1962].; GT
12.13100.
16.15150.
20.55200.
27.421273.15
29.799298.15
29.974300.
38.951400.
46.496500.
52.567600.
57.469700.
61.499800.
64.869900.
67.7201000.
70.1511100.
72.2371200.
74.0371300.
75.5931400.
76.9461500.

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

Quantity Value Units Method Reference Comment
Deltafliquid-46.19kcal/molCcbCox, 1961ALS
Deltafliquid-46.38 ± 0.26kcal/molCcbAndon, Biddiscombe, et al., 1960ALS
Deltafliquid-42.2kcal/molCcbPushin, 1954Author's hf298_condensed=-44.4 kcal/mol; ALS
Deltafliquid-46.25kcal/molCcbBadoche, 1941Author's hf298_condensed=-48.97 kcal/mol; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-885.44 ± 0.06kcal/molCcbCox, 1961Corresponding «DELTA»fliquid = -46.18 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-885.25 ± 0.14kcal/molCcbAndon, Biddiscombe, et al., 1960Corresponding «DELTA»fliquid = -46.37 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-889.4kcal/molCcbPushin, 1954Author's hf298_condensed=-44.4 kcal/mol; Corresponding «DELTA»fliquid = -42.2 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-885.37kcal/molCcbBadoche, 1941Author's hf298_condensed=-48.97 kcal/mol; Corresponding «DELTA»fliquid = -46.25 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Deltacliquid-883.0kcal/molCcbBarker, 1925Author was aware that data differs from previously reported values; Corresponding «DELTA»fliquid = -48.6 kcal/mol (simple calculation by NIST; no Washburn corrections); ALS
Quantity Value Units Method Reference Comment
liquid50.810cal/mol*KN/AAndon, Counsell, et al., 1967DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
53.760298.15Andon, Counsell, et al., 1967T = 10 to 400 K.; DH
52.8093.Rastorguev and Ganiev, 1967T = 293 to 373 K.; DH
52.29298.Tschamler and Krischai, 1951DH
51.79283.Bramley, 1916Mean value, 0 to 20 C.; DH

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

Quantity Value Units Method Reference Comment
Tboil475.2 ± 0.9KAVGN/AAverage of 18 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus284. ± 4.KAVGN/AAverage of 16 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple285.40KN/AAndon, Counsell, et al., 1967, 2Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc705.8KN/ADelaunois, 1968Uncertainty assigned by TRC = 0.4 K; TRC
Tc705.75KN/AAmbrose, 1963Uncertainty assigned by TRC = 0.45 K; TRC
Tc705.15KN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 2. K; TRC
Tc705.0KN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 2.5 K; TRC
Tc705.15KN/AGuye and Mallet, 1902, 2Uncertainty assigned by TRC = 2. K; accomipanied by some decomposition; TRC
Quantity Value Units Method Reference Comment
Pc43.03atmN/ADelaunois, 1968Uncertainty assigned by TRC = 5.807 atm; TRC
Pc45.0000atmN/AGlaser and Ruland, 1957Uncertainty assigned by TRC = 3.0000 atm; TRC
Pc45.00atmN/AGuye and Mallet, 1902Uncertainty assigned by TRC = 0.9000 atm; TRC
Pc44.9500atmN/AGuye and Mallet, 1902, 2Uncertainty assigned by TRC = 1.5000 atm; TRC
Pc45.0500atmN/AGuye and Mallet, 1902, 2Uncertainty assigned by TRC = 1.5000 atm; TRC
Quantity Value Units Method Reference Comment
Deltavap14. ± 3.kcal/molAVGN/AAverage of 8 values; Individual data points

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
15.1300.AStephenson and Malanowski, 1987Based on data from 285. - 416. K.; AC
12.6425.AStephenson and Malanowski, 1987Based on data from 410. - 477. K.; AC
11.4486.AStephenson and Malanowski, 1987Based on data from 471. - 531. K.; AC
10.5538.AStephenson and Malanowski, 1987Based on data from 523. - 633. K.; AC
13.1398.GS,EBStephenson and Malanowski, 1987Based on data from 383. - 473. K. See also Andon, Biddiscombe, et al., 1960, 2.; AC
14.5409.GSNasir, Hwang, et al., 1980Based on data from 388. - 429. K. See also Kkykj and Repas, 1973.; AC
14.1374.N/Avon Terres, Gebert, et al., 1955Based on data from 359. - 473. K. See also Boublik, Fried, et al., 1984.; AC
12.1448.N/AGoldblum, Martin, et al., 1947Based on data from 422. - 474. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
422.7 - 474.34.595861833.137-76.414Goldblum, Martin, et al., 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
13.4279.AStephenson and Malanowski, 1987Based on data from 273. - 285. K.; AC
14.7 ± 0.24284. - 313.GSAndon, Biddiscombe, et al., 1960, 2AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Method Reference Comment
2.175280.75N/AMeva'a and Lichanot, 1990DH
2.250285.0N/APoeti, Fanelli, et al., 1982DH
2.5590285.40N/AAndon, Counsell, et al., 1967DH
2.1282.3DSCRichard, Bernardes, et al., 2007AC
2.550285.3DSCJamróz, Palczewska-Tulinska, et al., 1998AC
2.560285.4N/ADomalski and Hearing, 1996AC
2.2280.8N/AMeva'a and Lichanot, 1990AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
7.6280.75Meva'a and Lichanot, 1990DH
7.894285.0Poeti, Fanelli, et al., 1982DH
6.580285.40Andon, Counsell, et al., 1967DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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:
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

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

C7H7O- + Hydrogen cation = Phenol, 3-methyl-

By formula: C7H7O- + H+ = C7H8O

Quantity Value Units Method Reference Comment
Deltar348.2 ± 1.2kcal/molCIDCAngel and Ervin, 2006gas phase; B
Deltar349.5 ± 2.1kcal/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar350.7 ± 2.3kcal/molG+TSKebarle and McMahon, 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar342.7 ± 2.0kcal/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Deltar343.8 ± 2.0kcal/molIMREKebarle and McMahon, 1977gas phase; B

Bromine anion + Phenol, 3-methyl- = (Bromine anion bullet Phenol, 3-methyl-)

By formula: Br- + C7H8O = (Br- bullet C7H8O)

Quantity Value Units Method Reference Comment
Deltar20.6 ± 1.8kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B,M
Quantity Value Units Method Reference Comment
Deltar23.cal/mol*KN/APaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar10.9 ± 1.0kcal/molIMREPaul and Kebarle, 1990gas phase; «DELTA»Gaff at 423 K; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
10.9423.PHPMSPaul and Kebarle, 1990gas phase; Entropy change calculated or estimated; M

m-Cresyl acetate + Water = Phenol, 3-methyl- + Acetic acid

By formula: C9H10O2 + H2O = C7H8O + C2H4O2

Quantity Value Units Method Reference Comment
Deltar-4.39 ± 0.14kcal/molCmSunner, 1957liquid phase; Heat of hydrolysis; ALS

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.

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

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


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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Mass spectrum
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Additional Data

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center, 1998.
NIST MS number 291279

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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.

Cox, 1961
Cox, J.D., The heats of combustion of phenol and the three cresols, Pure Appl. Chem., 1961, 2, 125-128. [all data]

Andon, Biddiscombe, et al., 1960
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F., Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc., 1960, 5246-5254. [all data]

Pushin, 1954
Pushin, N.A., Heats of combustion and heats of formation of isomeric organic compounds, Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]

Badoche, 1941
Badoche, M., No 19. - Chaleurs de combustion du phenol, du-m-cresol et del leurs ethers; par M. Marius BADOCHE., Bull. Soc. Chim. Fr., 1941, 8, 212-220. [all data]

Kudchadker S.A., 1978
Kudchadker S.A., Ideal gas thermodynamic properties of phenol and cresols, J. Phys. Chem. Ref. Data, 1978, 7, 417-423. [all data]

Green J.H.S., 1962
Green J.H.S., Normal frequencies, thermodynamic properties and equilibrium of the cresols, Chem. Ind. (London), 1962, 1575-1576. [all data]

Barker, 1925
Barker, M.F., Calorific value and constitution, J. Phys. Chem., 1925, 29, 1345-1363. [all data]

Andon, Counsell, et al., 1967
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F.; Mash, C.J., Thermodynamic properties of organic oxygen compounds. Part 17. Low-temperature heat capacity and entropy of the cresols, Trans. Faraday Soc., 1967, 63, 1115-1121. [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]

Tschamler and Krischai, 1951
Tschamler, H.; Krischai, H., Chinolin-m-Kresol, ein stark negatives System, Monatsh. Chem., 1951, 82, 259-270. [all data]

Bramley, 1916
Bramley, A., The study of binary mixtures. Part IV. Heats of reaction and specific heats, J. Chem. Soc. (London), 1916, 109, 496-515. [all data]

Andon, Counsell, et al., 1967, 2
Andon, R.J.L.; Counsell, J.F.; Lees, E.B.; Martin, J.F.; Mash, C.J., Thermodynamic Properties of Organic Oxygen Compounds Part 17. Low- temperature Heat Capacity and Entropy of the Cresols, Trans. Faraday Soc., 1967, 63, 1115. [all data]

Delaunois, 1968
Delaunois, C., Effect of the Filling Rate of a Reactor on the Vapor Tension and the Temperature at the Beginning of Cracking of Phenols at High Pressures, Ann. Mines Belg., 1968, No. 1, 9-16. [all data]

Ambrose, 1963
Ambrose, D., Critical Temperatures of Some Phenols and Other Organic Compounds, Trans. Faraday Soc., 1963, 59, 1988. [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]

Guye and Mallet, 1902
Guye, P.A.; Mallet, E., Critical Constant and Molecular Complexity of Several Organic Compds., C. R. Hebd. Seances Acad. Sci., 1902, 133, 168. [all data]

Guye and Mallet, 1902, 2
Guye, P.A.; Mallet, E., Measurement of Critical Constants, Arch. Sci. Phys. Nat., 1902, 13, 274-296. [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]

Andon, Biddiscombe, et al., 1960, 2
Andon, R.J.L.; Biddiscombe, D.P.; Cox, J.D.; Handley, R.; Harrop, D.; Herington, E.F.G.; Martin, J.F., 1009. Thermodynamic properties of organic oxygen compounds. Part I. Preparation and physical properties of pure phenol, cresols, and xylenols, J. Chem. Soc., 1960, 5246, https://doi.org/10.1039/jr9600005246 . [all data]

Nasir, Hwang, et al., 1980
Nasir, P.; Hwang, S.C.; Kobayashi, R., Development of an apparatus to measurement vapor pressures at high temperatures and its application to three higher-boiling compounds, J. Chem. Eng. Data, 1980, 25, 4, 298-301, https://doi.org/10.1021/je60087a009 . [all data]

Kkykj and Repas, 1973
Kkykj, J.; Repas, M., Petrochemia, 1973, 13, 179. [all data]

von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Brennst.-Chem., 1955, 36, 272. [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]

Goldblum, Martin, et al., 1947
Goldblum, K.B.; Martin, R.W.; Young, R.B., Vapor Pressure Data for Phenols, Ind. Eng. Chem., 1947, 39, 11, 1474-1476, https://doi.org/10.1021/ie50455a017 . [all data]

Meva'a and Lichanot, 1990
Meva'a, L.M.; Lichanot, A., Proprietes thermodynamiques en phase condensee des ortho, meta et para fluorotoluene, cresol et toluidine, Thermochim. Acta, 1990, 158, 335-345. [all data]

Poeti, Fanelli, et al., 1982
Poeti, G.; Fanelli, E.; Braghetti, M., A differential scanning calorimetric study of some phenol derivatives, J. Therm. Anal., 1982, 24(2), 273-279. [all data]

Richard, Bernardes, et al., 2007
Richard, Laurence S.; Bernardes, Carlos E.S.; Diogo, Hermínio P.; Leal, João P.; Minas da Piedade, Manuel E., Energetics of Cresols and of Methylphenoxyl Radicals, J. Phys. Chem. A, 2007, 111, 35, 8741-8748, https://doi.org/10.1021/jp073515m . [all data]

Jamróz, Palczewska-Tulinska, et al., 1998
Jamróz, Malgorzata E.; Palczewska-Tulinska, Marcela; Wyrzykowska-Stankiewicz, Danuta; Szafranski, Andrzej M.; Polaczek, Jerzy; Dobrowolski, Jan Cz.; Jamróz, Michal H.; Mazurek, Aleksander P., The urea--phenol(s) systems, Fluid Phase Equilibria, 1998, 152, 2, 307-326, https://doi.org/10.1016/S0378-3812(98)90206-0 . [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]

Angel and Ervin, 2006
Angel, L.A.; Ervin, K.M., Gas-phase acidities and O-H bond dissociation enthalpies of phenol, 3-methylphenol, 2,4,6-trimethylphenol, and ethanoic acid, J. Phys. Chem. A, 2006, 110, 35, 10392-10403, https://doi.org/10.1021/jp0627426 . [all data]

Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W., Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities, J. Am. Chem. Soc., 1981, 103, 4017. [all data]

Kebarle and McMahon, 1977
Kebarle, P.; McMahon, T.B., Intrinsic Acidities of Substituted Phenols and Benzoic Acids Determined by Gas Phase Proton Transfer Equilibria, J. Am. Chem. Soc., 1977, 99, 7, 2222, https://doi.org/10.1021/ja00449a032 . [all data]

Paul and Kebarle, 1990
Paul, G.J.C.; Kebarle, P., Stabilities in the Gas Phase of the Hydrogen Bonded Complexes, YC6H4OH-X-, of Substituted Phenols, YC6H4OH, with the Halide Anions X-(Cl-, Br-), Can. J. Chem., 1990, 68, 11, 2070, https://doi.org/10.1139/v90-316 . [all data]

Sunner, 1957
Sunner, S., The heat of hydrolysis of i-propenyl acetate and m-cresyl acetate and the heat of formation of acetone, Acta Chem. Scand., 1957, 11, 1757-1760. [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