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Phenol, 2-(1-methylethyl)-

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-175.3 ± 2.4kJ/molEqkNesterova, Pimerzin, et al., 1989Author was aware that data differs from previously reported values; Isomerization
Deltafgas-161.3kJ/molCcbBertholon, Giray, et al., 1971see Bertholon, 1967

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

Quantity Value Units Method Reference Comment
Deltafliquid-230.kJ/molCcbBertholon, Giray, et al., 1971see Bertholon, 1967
Quantity Value Units Method Reference Comment
Deltacliquid-5022.9kJ/molCcbBertholon, Giray, et al., 1971see Bertholon, 1967; Corresponding «DELTA»fliquid = -234. kJ/mol (simple calculation by NIST; no Washburn corrections)

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, Kenneth Kroenlein director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

Quantity Value Units Method Reference Comment
Tboil487. ± 2.KAVGN/AAverage of 9 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus290.00KN/ABertholon, 1967, 2Uncertainty assigned by TRC = 0.2 K; TRC
Tfus288.65KN/AKarr, 1957Uncertainty assigned by TRC = 2. K; TRC
Tfus288.65KN/Avon Terres, Gebert, et al., 1955Uncertainty assigned by TRC = 2. K; TRC
Tfus288.65KN/AStull, 1947Uncertainty assigned by TRC = 2. K; TRC
Quantity Value Units Method Reference Comment
Deltavap73.01kJ/molCBertholon, Giray, et al., 1971see Bertholon, 1967; ALS
Deltavap68.7kJ/molN/ABertholon, Giray, et al., 1971DRB

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
63.5390.EBNesterova, Nazmutdinov, et al., 1990Based on data from 375. - 493. K.; AC
55.1385.AStephenson and Malanowski, 1987Based on data from 370. - 489. K.; AC
56.1390.N/ATsvetkov, Nazmutdinov, et al., 1986Based on data from 375. - 493. K.; AC
57.3350.N/AStull, 1947, 2Based on data from 335. - 501. K.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
369.8 - 487.75.664132657.919-17.436von Terres, Gebert, et al., 1955, 2Coefficents calculated by NIST from author's data.

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

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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
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

C9H11O- + Hydrogen cation = Phenol, 2-(1-methylethyl)-

By formula: C9H11O- + H+ = C9H12O

Quantity Value Units Method Reference Comment
Deltar1454. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1423. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale; B

Phenol + Phenol, 2,4-bis(1-methylethyl)- = Phenol, 2-(1-methylethyl)- + p-Cumenol

By formula: C6H6O + C12H18O = C9H12O + C9H12O

Quantity Value Units Method Reference Comment
Deltar-0.7 ± 1.0kJ/molEqkNesterova, Pimerzin, et al., 1989liquid phase; Isomerization; ALS
Deltar-0.7 ± 1.0kJ/molEqkNesterova, Pilyshchikov, et al., 1983liquid phase; GC; ALS

Phenol, 2,4,6-tris(1-methylethyl)- + Phenol, 2-(1-methylethyl)- = Propofol + Phenol, 2,4-bis(1-methylethyl)-

By formula: C15H24O + C9H12O = C12H18O + C12H18O

Quantity Value Units Method Reference Comment
Deltar0.0 ± 0.84kJ/molEqkNesterova, Pilyshchikov, et al., 1983liquid phase; CG; ALS

Phenol, 2-(1-methylethyl)- = p-Cumenol

By formula: C9H12O = C9H12O

Quantity Value Units Method Reference Comment
Deltar-7.95 ± 0.21kJ/molEqkNesterova, Pilyshchikov, et al., 1983liquid phase; GC; ALS

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: John E. Bartmess

View reactions leading to C9H12O+ (ion structure unspecified)

De-protonation reactions

C9H11O- + Hydrogen cation = Phenol, 2-(1-methylethyl)-

By formula: C9H11O- + H+ = C9H12O

Quantity Value Units Method Reference Comment
Deltar1454. ± 9.2kJ/molG+TSFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale
Quantity Value Units Method Reference Comment
Deltar1423. ± 8.4kJ/molIMREFujio, McIver, et al., 1981gas phase; value altered from reference due to change in acidity scale

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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, 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 Japan AIST/NIMC Database- Spectrum MS-NW-5377
NIST MS number 229164

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.


Gas Chromatography

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), 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

Kovats' RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillarySE-30100.1178.Berezkin, Popova, et al., 199730. m/0.25 mm/0.5 «mu»m, He
CapillaryPS-255150.1175.Engewald, Billing, et al., 198850. m/0.30 mm/0.25 «mu»m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
Capillary5 % Phenyl methyl siloxane1184.Climent and Miranda, 1996He, 80. C @ 3. min, 20. K/min, 300. C @ 0. min; Column length: 25. m
CapillaryOV-11175.4Gautzsch and Zinn, 19968. K/min; Tstart: 35. C; Tend: 300. C
CapillaryDB-51203.Rostad and Pereira, 198630. m/0.26 mm/0.25 «mu»m, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min

Van Den Dool and Kratz RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryVF-5MS1198.9Mjøs, Meier, et al., 200650. m/0.25 mm/0.25 «mu»m, He; Program: 60C(2min) => 30C/min => 100C => 1C/min =>
CapillaryVF-5MS1199.2Mjøs, Meier, et al., 200650. m/0.25 mm/0.25 «mu»m, He; Program: 60C(2min) => 30C/min => 100C => 2C/min =>
CapillaryVF-5MS1200.2Mjøs, Meier, et al., 200650. m/0.25 mm/0.25 «mu»m, He; Program: 60C(2min) => 30C/min => 100C => 4C/min =>

Normal alkane RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryBP-11175.Health Safety Executive, 200050. m/0.22 mm/0.75 «mu»m, He, 5. K/min; Tstart: 50. C; Tend: 200. C
CapillaryUltra-11173.Okumura, 199125. m/0.32 mm/0.25 «mu»m, He, 3. K/min; Tstart: 80. C; Tend: 260. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryHP-51200.Zhao, Li, et al., 200830. m/0.25 mm/0.25 «mu»m; Program: 40 0C (2 min) 5 0C/min -> 80 0C 7 oC/min -> 160 0C 9 0C/min -> 200 0C 20 0C/min -> 280 0C (10 min)
CapillaryHP-51198.Zhao, Li, et al., 200830. m/0.25 mm/0.25 «mu»m; Program: not specified
CapillarySE-301200.Vinogradov, 2004Program: not specified
CapillaryDB-11175.Peng, 199630. m/0.53 mm/1.5 «mu»m; Program: 40 0C (4 min) 8 0C/min -> 200 0C (1 min) 5 0C/min -> 280 0C (20 min)

Normal alkane RI, polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-FFAP2111.Czerny, Brueckner, et al., 201130. m/0.32 mm/0.25 «mu»m, Helium, 40. C @ 2. min, 8. K/min, 230. C @ 5. min

Normal alkane RI, polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-Wax2089.Peng, 199630. m/0.53 mm/1.0 «mu»m; Program: 40 0C (4 min) 4 0C/min -> 200 0C (20 min)

Lee's RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-5203.41Rostad and Pereira, 198630. m/0.26 mm/0.25 «mu»m, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min

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), Gas Chromatography, Notes

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

Nesterova, Pimerzin, et al., 1989
Nesterova, T.N.; Pimerzin, A.A.; Rozhnov, A.M.; Karlina, T.N., Equilibria for the isomerization of (secondary-alkyl)phenols and cyclohexylphenols, J. Chem. Thermodyn., 1989, 21, 385-395. [all data]

Bertholon, Giray, et al., 1971
Bertholon, G.; Giray, M.; Perrin, R.; Vincent-Falquet-Berny, M.F., No. 532. - Etude physicochimique des phenols. OX. - Ethanlpies de combustion et energies de resonance des alcoyl et aryphenols, Bull. Soc. Chim. France, 1971, 3180-3187. [all data]

Bertholon, 1967
Bertholon, G., No. 534. - Etude physicochimique des phonols. VI. - Etude physicochimique des trois isopropylphenols isomeres, Bull. Soc. Chim. France, 1967, 8, 2977-2982. [all data]

Bertholon, 1967, 2
Bertholon, G., Physicochemical study of the phenols. VI. Physicochemical study of three isomeric isopropylphenols., Bull. Soc. Chim. Fr., 1967, No. 8, 2977. [all data]

Karr, 1957
Karr, C., , U. S. Bur. Mines, Inform. Circ. IC 7802, 1957. [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]

Stull, 1947
Stull, D.R., Organic compounds, Ind. Eng. Chem., 1947, 39, 517. [all data]

Nesterova, Nazmutdinov, et al., 1990
Nesterova, T.N.; Nazmutdinov, A.G.; Tsvetkov, V.S.; Rozhnov, A.M.; Roshchupkina, I. Yu, Vapour pressures and enthalpies of vaporization of alkylphenols, The Journal of Chemical Thermodynamics, 1990, 22, 4, 365-377, https://doi.org/10.1016/0021-9614(90)90122-7 . [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]

Tsvetkov, Nazmutdinov, et al., 1986
Tsvetkov, V.S.; Nazmutdinov, A.G.; Sharonov, K.S.; Rozhnov, A.M., Termodin. Org. Soedin., 1986, 71. [all data]

Stull, 1947, 2
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

von Terres, Gebert, et al., 1955, 2
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten, Brennst.-Chem., 1955, 36, 272-274. [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]

Nesterova, Pilyshchikov, et al., 1983
Nesterova, T.N.; Pilyshchikov, V.A.; Rozhnov, A.M., Chemical Equilibrium in the system isopropylphenols-phenol, J. Appl. Chem. USSR, 1983, 56, 1257-1261. [all data]

Berezkin, Popova, et al., 1997
Berezkin, V.G.; Popova, T.P.; Shiryayeva, V.Ye.; Nomura, N., Gas-chromatographic separation of monoalkylphenols on polar and non-polar phases by means of capillary chromatography, Pet. Chem. USSR (Engl. Transl.), 1997, 37, 2, 161-167. [all data]

Engewald, Billing, et al., 1988
Engewald, W.; Billing, U.; Topalova, I.; Petsev, N., Structure-retention correlations of alkylphenols in gas-liquid and gas-solid chromatography, J. Chromatogr., 1988, 446, 71-77, https://doi.org/10.1016/S0021-9673(00)94419-4 . [all data]

Climent and Miranda, 1996
Climent, M.J.; Miranda, M.A., Gas chromatographic - mass spectrometric study of photodegradation of carbamate pesticides, J. Chromatogr. A, 1996, 738, 2, 225-231, https://doi.org/10.1016/0021-9673(96)00084-2 . [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Mjøs, Meier, et al., 2006
Mjøs, S.A.; Meier, S.; Boitsov, S., Alkylphenol retention indices, J. Chromatogr. A, 2006, 1123, 1, 98-105, https://doi.org/10.1016/j.chroma.2006.05.002 . [all data]

Health Safety Executive, 2000
Health Safety Executive, MDHS 96 Volatile organic compounds in air - Laboratory method using pumed solid sorbent tubes, solvent desorption and gas chromatography in Methods for the Determination of Hazardous Substances (MDHS) guidance, Crown, Colegate, Norwich, 2000, 1-24, retrieved from http://www.hse.gov.uk/pubns/mdhs/pdfs/mdhs96.pdf. [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Zhao, Li, et al., 2008
Zhao, Y.; Li, J.; Xu, Y.; Duan, H.; Fan, W.; Zhao, G., EXtraction, preparation and identification of volatile compounds in Changyu XO brandy, Chinese J. Chromatogr., 2008, 26, 2, 212-222, https://doi.org/10.1016/S1872-2059(08)60014-0 . [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Peng, 1996
Peng, C.T., Gas chromatographic identification of aromatic hydrocarbons in Liquid Scintillation Spectrometry, Cook, G.T.; Harkness, D.D.; MacKenzie, A.B.; Miller, B.F.; Scott, E.M., ed(s)., 1996, 221-232. [all data]

Czerny, Brueckner, et al., 2011
Czerny, M.; Brueckner, R.; Kirchoff, E.; Schmitt, R.; Buettner, A., The influence of molecular structure on odor qualities and odor detection thresholds of volatile alkylated phenols, Chem. Senses, 2011, 1-15, retrieved from http://chemie.oxfordjournals.org. [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), Gas Chromatography, References