Phenol, 2,5-dimethyl-

• Formula: C₈H₁₀O
• Molecular weight: 122.1644
• IUPAC Standard InChI: InChI=1S/C8H10O/c1-6-3-4-7(2)8(9)5-6/h3-5,9H,1-2H3 Copy

  
• IUPAC Standard InChIKey: NKTOLZVEWDHZMU-UHFFFAOYSA-N Copy
• CAS Registry Number: 95-87-4
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: 2,5-Xylenol; p-Xylenol; 1-Hydroxy-2,5-dimethylbenzene; 1,2,5-Xylenol; 2,5-Dimethylphenol; 3,6-Dimethylphenol; 3,6-Xylenol; 6-Methyl-m-cresol; 1,4-Dimethyl-2-hydroxybenzene; 2,5-Dmp; 2-Hydroxy-p-xylene; NSC 2599
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• Information on this page:
  • Gas phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • UV/Visible spectrum
• 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:
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

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: Coblentz Society, Inc.

Condensed Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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

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

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

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Normal alkane RI, non-polar column, temperature ramp

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

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Normal alkane RI, polar column, temperature ramp

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Normal alkane RI, polar column, custom temperature program

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

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References

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

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]

Kudchadker S.A., 1979
Kudchadker S.A., Property data available for coal chemicals, Hydrocarbon Process., 1979, 58, 169-171. [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]

Zhang, Chen, et al., 1997
Zhang, M.; Chen, B.; Shen, S.; Chen, S., Compositional studies of high-temperature coal tar by g.c.-FT-i.r. analysis of middle oil fractions, Fuel, 1997, 76, 5, 415-423, https://doi.org/10.1016/S0016-2361(97)85518-4 . [all data]

Zhang, Li, et al., 1992
Zhang, M.J.; Li, S.D.; Chen, B.J., Compositional studies of high-temperature coal tar by GC/FTIR analysis of light oil fractions, Chromatographia, 1992, 33, 3/4, 138-146, https://doi.org/10.1007/BF02275894 . [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]

Tiess, 1984
Tiess, D., Gaschromatographische Retentionsindices von 125 leicht- bis mittelflüchtigen organischen Substanzen toxikologisch-analytischer Relevanz auf SE-30, Wiss. Z. Wilhelm-Pieck-Univ. Rostock Math. Naturwiss. Reihe, 1984, 33, 6-9. [all data]

Sellier, Tersac, et al., 1981
Sellier, F.; Tersac, G.; Guiochon, G., Étude de la polarité d'un poly(oxy aryl sulfonyl arylène) utilisé comme phase stationnaire en chromatographie gaz-liquide, J. Chromatogr., 1981, 219, 2, 213-224, https://doi.org/10.1016/S0021-9673(00)87931-5 . [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]

Gómez, Ledbetter, et al., 1993
Gómez, E.; Ledbetter, C.A.; Hartsell, P.L., Volatile compounds in apricot, plum, and their interspecific hybrids, J. Agric. Food Chem., 1993, 41, 10, 1669-1676, https://doi.org/10.1021/jf00034a029 . [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]

Varlet V., Knockaert C., et al., 2006
Varlet V.; Knockaert C.; Prost C.; Serot T., Comparison of odor-active volatile compounds of fresh and smoked salmon, J. Agric. Food Chem., 2006, 54, 9, 3391-3401, https://doi.org/10.1021/jf053001p . [all data]

Chung, Yung, et al., 2001
Chung, H.Y.; Yung, I.K.S.; Kim, J.-S., Comparison of volatile components in dried scallops (Chlamys farreri and Patinopecten yessoensis) prepared by boiling and steaming methods, J. Agric. Food Chem., 2001, 49, 1, 192-202, https://doi.org/10.1021/jf000692a . [all data]

Chevance and Farmer, 1999
Chevance, F.F.V.; Farmer, L.J., Identification of major volatile odor compounds in frankfurters, J. Agric. Food Chem., 1999, 47, 12, 5151-5160, https://doi.org/10.1021/jf990515d . [all data]

Chevance and Farmer, 1999, 2
Chevance, F.F.V.; Farmer, L.J., Release of volatile odor compounds from full-fat and reduced-fat frankfurters, J. Agric. Food Chem., 1999, 47, 12, 5161-5168, https://doi.org/10.1021/jf9905166 . [all data]

Chung, 1999
Chung, H.Y., Volatile components in crabmeats of Charybdis feriatus, J. Agric. Food Chem., 1999, 47, 6, 2280-2287, https://doi.org/10.1021/jf981027t . [all data]

Gruzdev, Kuzivanov, et al., 2012
Gruzdev, I.V.; Kuzivanov, I.M.; Zenkevich, I.G.; Kondratenok, B.M., Gas-chromatographic identification of products formed in iodination of methyl phenols by retention indices, Rus. J. Appl. Chem., 2012, 85, 9, 1355-1365, https://doi.org/10.1134/S1070427212090108 . [all data]

Souza, Re-Poppi, et al., 2012
Souza, J.B.G.; Re-Poppi, N.; Raposo, J.L.(Jr)., Characterization of pyroligneous acid used in agriculture by gas chromatography - mass spectrometry (in press), J. Braz. Chem. Soc., 2012, 00, 00, 1-8. [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]

Lee, Lee, et al., 2005
Lee, K.-G.; Lee, S.-E.; Takeoka, G.R.; Kim, J.-H.; Park, B.-S., Antioxidant activity and characterization of volatile constituents of beechwood creosote, J. Sci. Food Agric., 2005, 85, 9, 1580-1586, https://doi.org/10.1002/jsfa.2156 . [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]

Ansorena, Gimeno, et al., 2001
Ansorena, D.; Gimeno, O.; Astiasarán, I.; Bello, J., Analysis of volatile compounds by GC-MS of a dry fermented sausage: chorizo de Pamplona, Food Res. Int., 2001, 34, 1, 67-75, https://doi.org/10.1016/S0963-9969(00)00133-2 . [all data]

Geldon, 1989
Geldon, A.L., Ground Water Hydrology of the Central Raton Basin, Colorado and New Mexico, US Geological Survey, US Government Printing Office, 1989, 104. [all data]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Williams and Horne, 1995
Williams, P.T.; Horne, P.A., Analysis of aromatic hydrocarbons in pyrolytic oil derived from biomass, J. Anal. Appl. Pyrolysis, 1995, 31, 15-37, https://doi.org/10.1016/0165-2370(94)00814-H . [all data]

Donnelly, Abdel-Hamid, et al., 1993
Donnelly, J.R.; Abdel-Hamid, M.S.; Jeter, J.L.; Gurka, D.F., Application of gas chromatographic retention properties to the identification of environmental contaminants, J. Chromatogr., 1993, 642, 1-2, 409-415, https://doi.org/10.1016/0021-9673(93)80106-I . [all data]

Notes

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

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  ΔfH°gas	Enthalpy of formation of gas at standard conditions

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