Benzene, 1,2-dichloro-

• Formula: C₆H₄Cl₂
• Molecular weight: 147.002
• IUPAC Standard InChI: InChI=1S/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H Copy

  
• IUPAC Standard InChIKey: RFFLAFLAYFXFSW-UHFFFAOYSA-N Copy
• CAS Registry Number: 95-50-1
• 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.
• Isotopologues:
  • 1,2-Dichlorobenzene-D4
• Other names: Benzene, o-dichloro-; o-Dichlorobenzene; Cloroben; Dilantin DB; Dowtherm E; 1,2-Dichlorbenzene; 1,2-Dichlorobenzene; Chloroben; o-Dichlorobenzol; Dilatin db; ortho-Dichlorobenzene; o-Dichlorbenzene; o-Dichlorbenzol; Dichlorobenzene, o-; Dizene; DCB; NCI-C54944; ODB; ODCB; Special termite fluid; Termitkil; Chloroden; Dichlorobenzene, ortho; Orthodichlorobenzol; UN 1591; NSC 60644
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• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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

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

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

Entropy of fusion

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
LL - Sharon G. Lias and Joel F. Liebman
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

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₃Cl₂^- +  =

By formula: C₆H₃Cl₂^- + H⁺ = C₆H₄Cl₂

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, 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.

Platonov and Simulin, 1984
Platonov, V.A.; Simulin, Yu.N., Experimental determination of the standard enthalpies of formation of polychlorobenzenes. II. Standard enthalpies of formation of dichlorobenzenes, Russ. J. Phys. Chem. (Engl. Transl.), 1984, 58, 1630-1632. [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]

Kailuru and Abburi, 1988
Kailuru, R.; Abburi, K., Isobaric Vapor-Liquid Equilibria of Methyl Ethyl Ketone(1) + o-Dichlorobenzene(2), + Bromobenzene(2), and + Nitrobenzene(2), J. Chem. Eng. Data, 1988, 33, 251. [all data]

Walling and Miller, 1957
Walling, C.; Miller, B., The Relative Reactivities of Substituted Toluenes toward Chlorine Atoms, J. Am. Chem. Soc., 1957, 79, 4181. [all data]

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Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 2875-8. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [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]

An and Zheng, 1989
An, Xuwu; Zheng, Xiaolin, Determination of Standard Enthalpies of Vaporization and Sublimation of Three Dichlorobenzenes, Acta Phys. Chim. Sin., 1989, 5, 4, 487-491, https://doi.org/10.3866/PKU.WHXB19890421 . [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]

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

Grayson and Fosbraey, 2006
Grayson, B. Terence; Fosbraey, Lynda A., Determination of the vapour pressure of pesticides, Pestic. Sci., 2006, 13, 3, 269-278, https://doi.org/10.1002/ps.2780130308 . [all data]

Rohác, Ruzicka, et al., 1999
Rohác, Vladislav; Ruzicka, Vlastimil; Ruzicka, Kvetoslav; Polednicek, Milos; Aim, Karel; Jose, Jacques; Zábranský, Milan, Recommended vapour and sublimation pressures and related thermal data for chlorobenzenes, Fluid Phase Equilibria, 1999, 157, 1, 121-142, https://doi.org/10.1016/S0378-3812(99)00003-5 . [all data]

Rohác, Ruzicka, et al., 1998
Rohác, Vladislav; Ruzicka, Vlastimil; Ruzicka, Kvetoslav; Aim, Karel, Measurements of Saturated Vapor Pressure above the Liquid Phase for Isomeric Dichlorobenzenes and 1,2,4-Trichlorobenzene, J. Chem. Eng. Data, 1998, 43, 5, 770-775, https://doi.org/10.1021/je9701442 . [all data]

Polednicek, Guetachew, et al., 1996
Polednicek, M.; Guetachew, T.; Jose, J.; Ruzicka, V.; Rohac, V.; Zabransky, M., Vapor pressures and sublimation pressures of dichlorobenzenes (1,2-,1,3-, and 1,4-), trichlorobenzenes (1,2,3- and 1,3,5-), and pentachlorobenzene, ELDATA: Int. Electron. J. Phys. Chem. Data, 1996, 2, 2, 41. [all data]

Liu and Dickhut, 1994
Liu, Kewen; Dickhut, Rebecca M., Saturation vapor pressures and thermodynamic properties of benzene and selected chlorinated benzenes at environmental temperatures, Chemosphere, 1994, 29, 3, 581-589, https://doi.org/10.1016/0045-6535(94)90445-6 . [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]

McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds., J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009 . [all data]

Wei and Jin, 2009
Wei, Dongwei; Jin, Kexin, (Solid+liquid) equilibria of (naphthalene+isomeric dichlorobenzenes), The Journal of Chemical Thermodynamics, 2009, 41, 2, 145-149, https://doi.org/10.1016/j.jct.2008.10.005 . [all data]

Wei, 2008
Wei, Dongwei, (Solid+liquid) equilibria of (phenanthrene+dichlorobenzenes), Thermochimica Acta, 2008, 479, 1-2, 32-36, https://doi.org/10.1016/j.tca.2008.09.010 . [all data]

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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]

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Narbutt, J., Die Spezifischen Warmen und Schmelzwarmen der dichloro-, chlorbrom-, dibrom-, bromjod-, und dijodbenzole. I, Z. Elektrochem., 1918, 24, 339-342. [all data]

Steelhammer and Wentworth, 1969
Steelhammer, J.C.; Wentworth, W.E., Correlation of Electron Beam and Thermal Electron Attachment Studies for Some Chloro, Bromo, Iodo Aromatic Compounds, J. Chem. Phys., 1969, 51, 5, 1802, https://doi.org/10.1063/1.1672262 . [all data]

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Olesik, S.; Baer, T.; Morrow, J.C., Dissociation rates of energy-selected dichloro- and dibromobenzene ions, J. Phys. Chem., 1986, 90, 3563. [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. 1. Chlorobenzene and dichlorobenzenes, J. Phys. Chem., 1981, 85, 1486. [all data]

Maier and Marthaler, 1978
Maier, J.P.; Marthaler, O., Emission spectra of the radical cations of 1,3-dichlorobenzene, 1,4-dichlorobenzene and 1,3,5-trichlorobenzene in the gas phase, Chem. Phys., 1978, 32, 419. [all data]

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Lias, S.G.; Ausloos, P.J., eIonization energies of organic compounds by equilibrium measurements, J. Am. Chem. Soc., 1978, 100, 6027. [all data]

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

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Bralsford, R.; Harris, P.V.; Price, W.C., The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proc. Roy. Soc. (London), 1960, A258, 459. [all data]

Fujisawa, Oonishi, et al., 1991
Fujisawa, S.; Oonishi, I.; Masuda, S.; Ohno, K.; Harada, Y., Penning ionization electron spectroscopy of dichlorobenzenes, J. Phys. Chem., 1991, 95, 4250. [all data]

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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]

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

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Takhistov, V.V.; Ponomarev, D.A., Isodesmic reactions and thermochemistry of ions, Org. Mass Spectrom., 1994, 29, 395. [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]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH(+) ion,0K	Enthalpy of formation of positive ion at 0K
  ΔfH°gas	Enthalpy of formation of gas 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
  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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