Benzene, 1,2,4,5-tetrachloro-

• Formula: C₆H₂Cl₄
• Molecular weight: 215.892
• IUPAC Standard InChI: InChI=1S/C6H2Cl4/c7-3-1-4(8)6(10)2-5(3)9/h1-2H Copy

  
• IUPAC Standard InChIKey: JHBKHLUZVFWLAG-UHFFFAOYSA-N Copy
• CAS Registry Number: 95-94-3
• 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: s-Tetrachlorobenzene; 1,2,4,5-Tetrachlorobenzene; Rcra waste number U207
• 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
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas Chromatography
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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

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 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 solid

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
DH - Eugene S. Domalski and Elizabeth D. Hearing

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

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

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 by: 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

C₆HCl₄^- +  =

By formula: C₆HCl₄^- + H⁺ = C₆H₂Cl₄

C₆HCl₄^- +  =

By formula: C₆HCl₄^- + H⁺ = C₆H₂Cl₄

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

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:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Electron affinity determinations

Ionization energy determinations

De-protonation reactions

C₆HCl₄^- +  =

By formula: C₆HCl₄^- + H⁺ = C₆H₂Cl₄

C₆HCl₄^- +  =

By formula: C₆HCl₄^- + H⁺ = C₆H₂Cl₄

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 3800-1333, 10% IN CS2 FOR 1333-400 CM^-1) VS. SOLVENT; DOW KBr FOREPRISM-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

UV/Visible 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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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

Platonov and Simulin, 1983
Platonov, V.A.; Simulin, Yu.N., Standard enthalpies of formation of 1,2,3-trichlorobenzene, 1,2,4,5-tetrachlorobenzene, and hexachlorobenzene, Russ. J. Phys. Chem. (Engl. Transl.), 1983, 57, 840-842. [all data]

Andrews and Haworth, 1928
Andrews, D.H.; Haworth, E., An application of the rule of Dulong and Petit to molecules, J. Am. Chem. Soc., 1928, 50, 2998-3002. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Miller, Ghodbane, et al., 1984
Miller, M.M.; Ghodbane, S.; Wasik, S.P.; Tewari, Y.B.; Martire, D.E., Aqueous Solubilities, Octanol/Water Partition Coefficients, and Entropies of Melting of Chlorinated Benzenes and Biphenyls, J. Chem. Eng. Data, 1984, 29, 184-190. [all data]

White, Biggs, et al., 1940
White, A.H.; Biggs, B.S.; Morgan, S.O., Dielectric Evidence for Molecular Rotation in the Crystals of Certain Benzene Derivatives, J. Am. Chem. Soc., 1940, 62, 16-25. [all data]

Sabbah and An, 1991
Sabbah, R.; An, X.W., Etude thermodynamique des chlorobenzenes, Thermochim. Acta, 1991, 179, 81-88. [all data]

Spieksma, Luijk, et al., 1994
Spieksma, Walter; Luijk, Ronald; Govers, Harrie A.J., Determination of the liquid vapour pressure of low-volatility compounds from the Kováts retention index, Journal of Chromatography A, 1994, 672, 1-2, 141-148, https://doi.org/10.1016/0021-9673(94)80602-0 . [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]

Rai, Pandey, et al., 2002
Rai, U.S.; Pandey, Pinky; Rai, R.N., Physical chemistry of binary organic eutectic and monotectic alloys; 1,2,4,5-tetrachlorobenzene--α-naphthol and TCB--resorcinol systems, Materials Letters, 2002, 53, 1-2, 83-90, https://doi.org/10.1016/S0167-577X(01)00458-X . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Mondieig, Cuevas-Kiarte, et al., 1989
Mondieig, D.; Cuevas-Kiarte, M.A.; Haget, Y., Polymorphisme du tetrachloro-1,2,4,5-benzene et du tetrabromo-1,2,4,5-benzene, J. Therm. Anal., 1989, 35(7), 2491-2500. [all data]

Mondieig, Housty, et al., 1987
Mondieig, D.; Housty, J.R.; Haget, Y., The Guinier-Lenne method in DSC. Polymorphysm of tetrasubstituted derivatives of benzene and their mixtures, Calorim. Anal. Therm., 1987, 18, 269-275. [all data]

Martin, 1982
Martin, C.A., Specific heat anomalies in some organic compounds, Therm. Anal., Proc. Int. Conf., 7th, 1982, 2, 829-835. [all data]

Schlosser, Marzi, et al., 2001
Schlosser, M.; Marzi, E.; Cottet, F.; Buker, H.H.; Nibbering, N.M.M., The acidity of chloro-substituted benzenes: A comparison of gas phase, ab initio, and kinetic data, Chem. Eur. J., 2001, 7, 16, 3511-3516, https://doi.org/10.1002/1521-3765(20010817)7:16<3511::AID-CHEM3511>3.0.CO;2-U . [all data]

Chen and Wentworth, 1981
Chen, E.C.M.; Wentworth, W.E., Correlation and Prediction of Electron Capture Response from Molecular Parameters, J. Chromatogr., 1981, 217, 151, https://doi.org/10.1016/S0021-9673(00)88069-3 . [all data]

Ruscic, Klasinc, et al., 1981
Ruscic, B.; Klasinc, L.; Wolf, A.; Knop, J.V., Photoelectron spectra of and Ab initio calculations on chlorobenzenes. 2. Trichlorobenzenes, tetrachlorobenzenes, and pentachlorobenzene, J. Phys. Chem., 1981, 85, 1490. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Dougherty and McGlynn, 1977
Dougherty, D.; McGlynn, S.P., Photoelectron spectroscopy of carbonyls. 1,4-Benzoquinones, J. Am. Chem. Soc., 1977, 99, 3234. [all data]

Streets and Ceasar, 1973
Streets, D.G.; Ceasar, G.P., Inductive mesomeric effects on the π orbitals of halobenzenes, Mol. Phys., 1973, 26, 1037. [all data]

Jondorf and Williams, 1958
Jondorf, W.R.; Williams, R.T., Biochem. J., 1958, 69, 181. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid 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
  ΔsubH°	Enthalpy of sublimation 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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