Benzene, (bromomethyl)-

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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

Quantity Value Units Method Reference Comment
Δfgas84. ± 4.kJ/molEqkBenson and Buss, 1957 

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

Quantity Value Units Method Reference Comment
Δfliquid22.kJ/molCmHolm, 1973Grignard Rx
Δfliquid16. ± 2.kJ/molChydAshcroft, Carson, et al., 1963 
Δfliquid30. ± 14.kJ/molCmFowell and Mortimer, 1961 

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

Quantity Value Units Method Reference Comment
Tboil471.7KN/AAldrich Chemical Company Inc., 1990BS
Tboil471.KN/ABuckingham and Donaghy, 1982BS
Tboil471.KN/ABuckingham and Donaghy, 1982BS
Quantity Value Units Method Reference Comment
Tfus271.75KN/AAshcroft, 1976Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Δvap53.3 ± 0.7kJ/molGSKrasnykh, Vasiltsova, et al., 2002Based on data from 284. to 306. K.; AC
Δvap53.7kJ/molCGCKrasnykh, Vasiltsova, et al., 2002AC
Δvap50.5 ± 0.5kJ/molN/AAshcroft, 1976, 2AC
Δvap47.3 ± 4.2kJ/molVBenson and Buss, 1957ALS

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
400.0.11Buckingham and Donaghy, 1982BS
400.0.11Buckingham and Donaghy, 1982BS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
46.9320.AStephenson and Malanowski, 1987Based on data from 305. to 472. K. See also Stull, 1947 and Dykyj, Svoboda, et al., 1999.; AC
48.1355.I,AAshcroft, 1976, 2Based on data from 340. to 409. K. See also Stephenson and Malanowski, 1987.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference Comment
305.4 to 471.74.673422043.135-34.57Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
13.2271.8Ashcroft, 1976, 2AC

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Benzene, (bromomethyl)- (l) + magnesium (cr) = C7H7BrMg (solution)

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

Quantity Value Units Method Reference Comment
Δr-275.7 ± 4.4kJ/molRSCHolm, 1981solvent: Diethyl ether; Due to the possibility of side reactions, the enthalpy of reaction was not considered to be sufficiently reliable for deriving the enthalpy of formation of the Grignard reagent Holm, 1981; MS

C7H6Br- + Hydrogen cation = Benzene, (bromomethyl)-

By formula: C7H6Br- + H+ = C7H7Br

Quantity Value Units Method Reference Comment
Δr1557. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; acidity comparable to MeCN, between HF and tBuCH(Me)OH; B
Quantity Value Units Method Reference Comment
Δr1527. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; acidity comparable to MeCN, between HF and tBuCH(Me)OH; B

Hydrogen bromide + Benzene, (bromomethyl)- = Toluene + Bromine

By formula: HBr + C7H7Br = C7H8 + Br2

Quantity Value Units Method Reference Comment
Δr33.9 ± 4.2kJ/molEqkBenson and Buss, 1957gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 33. ± 4. kJ/mol; ALS

Stannane, trimethyl(phenylmethyl)- (l) + Bromine (g) = Benzene, (bromomethyl)- (l) + C3H9BrSn (l)

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

Quantity Value Units Method Reference Comment
Δr-226.6 ± 0.9kJ/molRSCPedley and Skinner, 1959Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970, 2.; MS

Benzene, (bromomethyl)- + Water = Hydrogen bromide + Benzyl alcohol

By formula: C7H7Br + H2O = HBr + C7H8O

Quantity Value Units Method Reference Comment
Δr-7.9kJ/molCmGellner and Skinner, 1949liquid phase; Heat of hydrloysis; ALS

C12H7MnO5 (cr) + 1.5Bromine (g) = Benzene, (bromomethyl)- (g) + manganese dibromide (cr) + 5Carbon monoxide (g)

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

Quantity Value Units Method Reference Comment
Δr-194.5 ± 7.8kJ/molHAL-HFCConnor, Zafarani-Moattar, et al., 1982MS

Benzene, (bromomethyl)- + 0.5Hydrogen = Toluene + 0.5Bromine

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

Quantity Value Units Method Reference Comment
Δr-4. ± 2.kJ/molChydAshcroft, Carson, et al., 1963liquid phase; ALS

Benzene, (bromomethyl)- + C4H9Li = Benzene, pentyl- + Lithium bromide

By formula: C7H7Br + C4H9Li = C11H16 + BrLi

Quantity Value Units Method Reference Comment
Δr-338. ± 11.kJ/molCmFowell and Mortimer, 1961liquid phase; ALS

Gas Chromatography

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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

Normal alkane RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillarySE-301087.Krasnykh, Vasiltsova, et al., 2002Nitrogen, 30. C @ 5. min, 10. K/min; Column length: 25. m; Tend: 250. C

Normal alkane RI, non-polar column, custom temperature program

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Column type Active phase I Reference Comment
CapillaryPolydimethyl siloxanes1059.Zenkevich and Chupalov, 1996Program: not specified
CapillaryDB-11061.Hathcock and Bertsch, 1993100. m/0.25 mm/0.5 μm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, Notes

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]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Hathcock and Bertsch, 1993
Hathcock, S.; Bertsch, W., Analysis of volatiles associated with industrial scale processing of expanded polystyrene. Part II: Identification and quantitation, J. Hi. Res. Chromatogr., 1993, 16, 11, 651-659, https://doi.org/10.1002/jhrc.1240161106 . [all data]


Notes

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