Benzene, bromo-

• Formula: C₆H₅Br
• Molecular weight: 157.008
• IUPAC Standard InChI: InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H Copy

  
• IUPAC Standard InChIKey: QARVLSVVCXYDNA-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-86-1
• 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.
• Other names: Bromobenzene; Monobromobenzene; Phenyl bromide; 1-Bromobenzene; NCI-C55492; UN 2514
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible 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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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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 (atm)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

Go To: Top, Phase change data, 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

C₆H₄Br^- +  =

By formula: C₆H₄Br^- + H⁺ = C₆H₅Br

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆H₅Br = (C₆H₇N⁺ • C₆H₅Br)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₆H₄Br^- +  =

By formula: C₆H₄Br^- + H⁺ = C₆H₅Br

C₆H₄Br^- +  =

By formula: C₆H₄Br^- + H⁺ = C₆H₅Br

 +  = C₈H₉Br + 

By formula: C₈H₁₀ + C₆H₅Br = C₈H₉Br + C₆H₆

2 +  =  + 2

By formula: 2C₆H₅Br + Br₂Hg = C₁₂H₁₀Hg + 2Br₂

 +  = ( • )

By formula: Cl^- + C₆H₅Br = (Cl^- • C₆H₅Br)

Mass spectrum (electron ionization)

Go To: Top, Phase change data, Reaction thermochemistry 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, Phase change data, Reaction thermochemistry 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.

Marsh, 1987
Marsh, K.N., Recommended Reference Materials for the Realization of Physicochemical Properties, Blackwell Sci. Pub., Oxford, 1987. [all data]

Masi and Scott, 1975
Masi, J.F.; Scott, R.B., Some thermodynamic properties of bromobenzene from 0 to 1500k, J. Res. Natl. Bur. Stand., Sect. A, 1975, 79, 619-28. [all data]

Stull, 1937
Stull, D.R., A Semi-micro Calorimeter for Measuring Heat Capacities at Low Temp., J. Am. Chem. Soc., 1937, 59, 2726. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [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]

Wadsö, Luoma, et al., 1968
Wadsö, Ingemar; Luoma, Sinikka; Olson, Thomas; Norin, Torbjörn, Heats of Vaporization of Organic Compounds. II. Chlorides, Bromides, and Iodides., Acta Chem. Scand., 1968, 22, 2438-2444, https://doi.org/10.3891/acta.chem.scand.22-2438 . [all data]

Wadso, 1968
Wadso, I., Heats of vaporization of organic compounds II. Chlorides, bromides, and iodides, Acta Chem. Scand., 1968, 22, 2438. [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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [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]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Masi and Scott, 1975, 2
Masi, Joseph F.; Scott, Russell B., Some thermodynamic properties of bromobenzene from 0 to 1500 K, J. RES. NATL. BUR. STAN. SECT. A., 1975, 79A, 5, 619, https://doi.org/10.6028/jres.079A.022 . [all data]

Dreyer, Martin, et al., 1955
Dreyer, R.; Martin, W.; von Weber, U., Die S«65533»ttigungsdampfdrucke von Benzol, Toluol, «65533»thylbenzol, Styrol, Cumol und Brombenzol zwischen 10 und 760 Torr, J. Prakt. Chem., 1955, 1, 5-6, 324-328, https://doi.org/10.1002/prac.19550010508 . [all data]

Masi and Scott, 1975, 3
Masi, J.F.; Scott, R.B., Some thermodynamic properties of bromobenzene from 0 to 1500K, J. Res., 1975, NBS 79A, 619-628. [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Stull, 1937, 2
Stull, D.R., A semi-micro calorimeter for measuring heat capacities at low temperatures, J. Am. Chem. Soc., 1937, 59, 2726-2733. [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method, J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105 . [all data]

Linnert and Riveros, 1994
Linnert, H.V.; Riveros, J.M., Benzyne-related mechanisms in the gas phase ion molecule reactions of haloarenes, Int. J. Mass Spectrom. Ion Proc., 1994, 140, 1, 163, https://doi.org/10.1016/0168-1176(94)04079-6 . [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Merdzhanov, Alenin, et al., 1982
Merdzhanov, V.R.; Alenin, V.I.; Nesterova, T.N.; Rozhnov, A.M., Study of equilibrium transformation of ethylbromobenzenes, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1982, 25, 1047-1049. [all data]

Chernick, Skinner, et al., 1956
Chernick, C.L.; Skinner, H.A.; Wadso, I., Thermochemistry of metallic alkyls. Part 7.-The heat of formation of mercury diphenyl, and of mercury phenyl chloride, Trans. Faraday Soc., 1956, 52, 1088-1093. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Notes

Go To: Top, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  T	Temperature
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy 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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