Benzene, (bromomethyl)-

• Formula: C₇H₇Br
• Molecular weight: 171.034
• IUPAC Standard InChI: InChI=1S/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2 Copy

  
• IUPAC Standard InChIKey: AGEZXYOZHKGVCM-UHFFFAOYSA-N Copy
• CAS Registry Number: 100-39-0
• 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: Benzyl bromide; Toluene, α-bromo-; α-Bromotoluene; ω-Bromotoluene; (Bromomethyl)benzene; Bromophenylmethane; 1-Bromotoluene; Bromotoluene, α; UN 1737; NSC 8041; Phenylmethyl bromide
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• 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 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 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 (atm)
    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:
MS - José A. Martinho Simões
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

 (l) +  (cr) = C₇H₇BrMg (solution)

By formula: C₇H₇Br (l) + Mg (cr) = C₇H₇BrMg (solution)

C₇H₆Br^- +  =

By formula: C₇H₆Br^- + H⁺ = C₇H₇Br

 +  =  + 

By formula: HBr + C₇H₇Br = C₇H₈ + Br₂

 (l) +  (g) =  (l) + C₃H₉BrSn (l)

By formula: C₁₀H₁₆Sn (l) + Br₂ (g) = C₇H₇Br (l) + C₃H₉BrSn (l)

 +  =  + 

By formula: C₇H₇Br + H₂O = HBr + C₇H₈O

C₁₂H₇MnO₅ (cr) + 1.5 (g) =  (g) +  (cr) + 5 (g)

By formula: C₁₂H₇MnO₅ (cr) + 1.5Br₂ (g) = C₇H₇Br (g) + Br₂Mn (cr) + 5CO (g)

 + 0.5 =  + 0.5

By formula: C₇H₇Br + 0.5H₂ = C₇H₈ + 0.5Br₂

 + C₄H₉Li =  + 

By formula: C₇H₇Br + C₄H₉Li = C₁₁H₁₆ + BrLi

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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₆Br^- +  =

By formula: C₇H₆Br^- + H⁺ = C₇H₇Br

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

Gas Phase Spectrum

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Additional Data

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.

Benson and Buss, 1957
Benson, S.W.; Buss, J.H., The thermodynamics of bromination of toluene and the heat of formation of the benzyl radical, J. Phys. Chem., 1957, 61, 104-109. [all data]

Holm, 1973
Holm, T., Thermochemistry of Grignard reagents. Enthalpies of formation of alkylmagnesium bromides and of alkyl bromides, J. Organomet. Chem., 1973, 56, 87-93. [all data]

Ashcroft, Carson, et al., 1963
Ashcroft, S.J.; Carson, A.S.; Pedley, J.B., Thermochemistry of reductions caused by lithium aluminium hydride. Part 2.-The heats of formation of benzyl bromide, benzyl iodide and the benzyl radical, Trans. Faraday Soc., 1963, 59, 2713-2717. [all data]

Fowell and Mortimer, 1961
Fowell, P.A.; Mortimer, C.T., 735. Heats of formation and bond energies. Part V. n-Butyl-lithium, J. Chem. Soc., 1961, 3793-3796. [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]

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

Ashcroft, 1976
Ashcroft, S.J., J. Chem. Eng. Data, 1976, 21, 397. [all data]

Krasnykh, Vasiltsova, et al., 2002
Krasnykh, Eugen L.; Vasiltsova, Tatiana V.; Verevkin, Sergey P.; Heintz, Andreas, Vapor Pressures and Enthalpies of Vaporization of Benzyl Halides and Benzyl Ethers, J. Chem. Eng. Data, 2002, 47, 6, 1372-1378, https://doi.org/10.1021/je020034h . [all data]

Ashcroft, 1976, 2
Ashcroft, Stanley J., Vapor pressures and enthalpies of vaporization of benzyl halides, J. Chem. Eng. Data, 1976, 21, 4, 397-398, https://doi.org/10.1021/je60071a009 . [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]

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]

Holm, 1981
Holm, T., J. Chem. Soc., Perkin Trans. II, 1981, 464.. [all data]

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Pedley and Skinner, 1959
Pedley, J.B.; Skinner, H.A., Thermochemistry of metallic alkyls. Part 9.?Heats of bromination of some organo-tin compounds, Trans. Faraday Soc., 1959, 55, 544, https://doi.org/10.1039/tf9595500544 . [all data]

Pedley and Rylance, 1977
Pedley, J.B.; Rylance, J., Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brigton, 1977. [all data]

Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds in Academic Press, New York, 1970. [all data]

Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A., Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X, J. Chem. Soc., 1949, 1145-1148. [all data]

Connor, Zafarani-Moattar, et al., 1982
Connor, J.A.; Zafarani-Moattar, M.T.; Bickerton, J.; El-Saied, N.I.; Suradi, S.; Carson, R.; Al Takkhin, G.; Skinner, H.A., Organomet., 1982, 1, 1166. [all data]

Traeger and Kompe, 1990
Traeger, J.C.; Kompe, B.M., Threshold C₇H₇ formation from the benzyl halides by photoionization mass spectrometry, Int. J. Mass Spectrom. Ion Processes, 1990, 101, 111. [all data]

Baer, Morrow, et al., 1988
Baer, T.; Morrow, J.C.; Shao, J.D.; Olesik, S., Gas-phase heats of formation of C₇H₇⁺ isomers: m-Tolyl, p-tolyl, and benzyl ions, J. Am. Chem. Soc., 1988, 110, 5633. [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]

Grutzmacher, 1970
Grutzmacher, H.-F., Zum Mechanismus massenspektrometrischer Fragmentierungsreaktionen-IV: zur Bildung von Phenonium-Ionen bei der Elektronenstoss-Fragmentierung von -Phenylathylbromiden, Org. Mass Spectrom., 1970, 3, 131. [all data]

Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G., Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH₂-R, Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]

Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A., C-Hal hyperkonjugation, Tetrahedron Lett., 1973, 981. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation 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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