Benzene, 1-chloro-4-methyl-

• Formula: C₇H₇Cl
• Molecular weight: 126.583
• IUPAC Standard InChI: InChI=1S/C7H7Cl/c1-6-2-4-7(8)5-3-6/h2-5H,1H3 Copy

  
• IUPAC Standard InChIKey: NPDACUSDTOMAMK-UHFFFAOYSA-N Copy
• CAS Registry Number: 106-43-4
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Toluene, p-chloro-; p-Chlorotoluene; p-Tolyl chloride; 1-Chloro-4-methylbenzene; 4-Chloro-1-methylbenzene; 4-Chlorotoluene; para-Chlorotoluene; 1-Methyl-4-chlorobenzene; 4-Tolyl chloride; 4-Methylphenyl chloride; NSC 404114
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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  • Gas Phase Kinetics Database
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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

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, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy 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
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

C₇H₆Cl^- +  =

By formula: C₇H₆Cl^- + H⁺ = C₇H₇Cl

 +  =  + 

By formula: C₇H₇Cl + C₁₃H₁₉Cl = C₁₀H₁₃Cl + C₁₀H₁₃Cl

Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₆Cl^- +  =

By formula: C₇H₆Cl^- + H⁺ = C₇H₇Cl

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 3800-1300, 2% IN CS2 FOR 1300-650, AND 10% IN CCl4 FOR 650-240 CM^-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

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

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Normal alkane RI, non-polar column, isothermal

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

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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

Go To: Top, 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.

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [all data]

Simon, 1957
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]

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]

Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav, Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data, Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I . [all data]

Mathews, 1926
Mathews, J.H., The accurate measurement of heats of vaporization of liquids, J. Am. Chem. Soc., 1926, 48, 562-576. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R., Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [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]

Stull, 1947
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]

van Miltenburg, Alvarez-Larena, et al., 1996
van Miltenburg, J.C.; Alvarez-Larena, A.; Labrador, M.; Palacios, L.; Rodriguez-Romero, J.; Tauler, E.; Estop, E., The thermal properties of three (Cl-, Br-, I-) para-halotoluenes. Formation of glassy crystals, Thermochimica Acta, 1996, 273, 31-42, https://doi.org/10.1016/0040-6031(95)02596-0 . [all data]

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

Nesterova, Rozhnov, et al., 1985
Nesterova, T.N.; Rozhnov, A.M.; Malova, T.N.; Kovzel, E.N., Molar enthalpies of formation of isopropylchlorobenzenes derived from equilibrium measurements, J. Chem. Thermodyn., 1985, 17, 649-656. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Tajima and Tsuchiya, 1972
Tajima, S.; Tsuchiya, T., The effects of the repeller voltage and the shield voltage on appearance potential measurements by electron impact, Shitsuryo Bunseki, 1972, 20, 117. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Domnin, Lakshin, et al., 1985
Domnin, I.N.; Lakshin, A.M.; Misharev, A.D.; Orlov, V.M.; Takhistov, V.V., Thermochemical investigation of some hydrocarbon ions generated by photoionization, J. Org. Chem. USSR, 1985, 21, 1149. [all data]

Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T., Energetics consideration of C₅H₅⁺ ions produced from various precursors by electron impact, Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]

Selim, Rabbih, et al., 1994
Selim, E.T.M.; Rabbih, M.A.; Fahmey, M.A.; Hawash, M.F., Loss of H and Cl from the molecular ions of chlorotoluene isomers using electron impact mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1994, 134, 119. [all data]

McLafferty and Winkler, 1974
McLafferty, F.W.; Winkler, J., Gaseous tropylium, benzyl, tolyl, and norbornadienyl cations, J. Am. Chem. Soc., 1974, 96, 5182. [all data]

Yeo and Williams, 1970
Yeo, A.N.H.; Williams, D.H., Rearrangement in the molecular ions of halogenotoluenes prior to fragmentation in the mass spectrometer, Chem. Commun., 1970, 886. [all data]

Brown, 1970
Brown, P., Kinetic studies in mass spectrometry-IV. The [M - Cl] reaction in substituted chlorobenzenes and the question of molecular ion isomerization, Org. Mass Spectrom., 1970, 3, 639. [all data]

Guan, Kiraly, et al., 1989
Guan, Y.; Kiraly, J.; Rijks, J.A., Interactive retention index database for compound identification in temperature-programmed capillary gas chromatography, J. Chromatogr., 1989, 472, 129-143, https://doi.org/10.1016/S0021-9673(00)94101-3 . [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]

Censullo, Jones, et al., 2003
Censullo, A.C.; Jones, D.R.; Wills, M.T., Speciation of the volatile organic compounds (VOCs) in solventborne aerosol coatings by solid phase microextraction-gas chromatography, J. Coat. Technol., 2003, 75, 936, 47-53, https://doi.org/10.1007/BF02697922 . [all data]

Sun and Stremple, 2003
Sun, G.; Stremple, P., Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [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]

Bermejo, Moinelo, et al., 1980
Bermejo, J.; Moinelo, S.R.; Suarez Canga, C., Calculo de indices de retencion a patir de DI y de la polaridad de la fase, Calculo de indices de retencion a patir de DI y de la polaridad de la fase, Instituto Nacional del Carbon y sus Derivados Francisco Pintado Fe (INCAR), La Corredoria, Oviedo, Espana, 1980, 13. [all data]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Sorimachi, Tanabe, et al., 1995
Sorimachi, J.; Tanabe, A.; Mitobe, H.; Kuniaki, K.; Masaaki, S., Programmed temperature retention indices for volatile organic compounds on headspace GC/MS analysis, Niigata-ken Eisei Kogai Kenkyusho Nenpo, 1995, 11, 75-79. [all data]

Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J., Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning, Analyst, 1992, 117, 7, 1111-1127, https://doi.org/10.1039/an9921701111 . [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]

Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [all data]

Vrana, Paschke, et al., 2005
Vrana, B.; Paschke, H.; Paschke, A.; Popp, P.; Schuurmann, G., Performance of semipermeable membrane devices for sampling of organic contaminants in groun water, J. Envirom. Monit., 2005, 7, 5, 500-508, https://doi.org/10.1039/b411645c . [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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