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:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
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  • Gas Chromatography
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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

References

Go To: Top, Reaction thermochemistry data, Notes

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

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]

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]

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]

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]

Notes

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• Symbols used in this document:
  

  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

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