Benzene, (bromomethyl)-
- Formula: C7H7Br
- Molecular weight: 171.034
- IUPAC Standard InChIKey: AGEZXYOZHKGVCM-UHFFFAOYSA-N
- 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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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 |
---|---|---|---|---|---|
ΔfH°gas | 84. ± 4. | kJ/mol | Eqk | Benson 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 |
---|---|---|---|---|---|
ΔfH°liquid | 22. | kJ/mol | Cm | Holm, 1973 | Grignard Rx |
ΔfH°liquid | 16. ± 2. | kJ/mol | Chyd | Ashcroft, Carson, et al., 1963 | |
ΔfH°liquid | 30. ± 14. | kJ/mol | Cm | Fowell 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 |
---|---|---|---|---|---|
Tboil | 471.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 471. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tboil | 471. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 271.75 | K | N/A | Ashcroft, 1976 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 53.3 ± 0.7 | kJ/mol | GS | Krasnykh, Vasiltsova, et al., 2002 | Based on data from 284. to 306. K.; AC |
ΔvapH° | 53.7 | kJ/mol | CGC | Krasnykh, Vasiltsova, et al., 2002 | AC |
ΔvapH° | 50.5 ± 0.5 | kJ/mol | N/A | Ashcroft, 1976, 2 | AC |
ΔvapH° | 47.3 ± 4.2 | kJ/mol | V | Benson and Buss, 1957 | ALS |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
400. | 0.11 | Buckingham and Donaghy, 1982 | BS |
400. | 0.11 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
46.9 | 320. | A | Stephenson and Malanowski, 1987 | Based on data from 305. to 472. K. See also Stull, 1947 and Dykyj, Svoboda, et al., 1999.; AC |
48.1 | 355. | I,A | Ashcroft, 1976, 2 | Based 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 471.7 | 4.67342 | 2043.135 | -34.57 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.2 | 271.8 | Ashcroft, 1976, 2 | AC |
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -275.7 ± 4.4 | kJ/mol | RSC | Holm, 1981 | solvent: 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- + =
By formula: C7H6Br- + H+ = C7H7Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1557. ± 8.8 | kJ/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; acidity comparable to MeCN, between HF and tBuCH(Me)OH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1527. ± 8.4 | kJ/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; acidity comparable to MeCN, between HF and tBuCH(Me)OH; B |
By formula: HBr + C7H7Br = C7H8 + Br2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33.9 ± 4.2 | kJ/mol | Eqk | Benson and Buss, 1957 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 33. ± 4. kJ/mol; ALS |
(l) +
(g) =
(l) + C3H9BrSn (l)
By formula: C10H16Sn (l) + Br2 (g) = C7H7Br (l) + C3H9BrSn (l)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -226.6 ± 0.9 | kJ/mol | RSC | Pedley and Skinner, 1959 | Please also see Pedley and Rylance, 1977 and Cox and Pilcher, 1970, 2.; MS |
By formula: C7H7Br + H2O = HBr + C7H8O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -7.9 | kJ/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrloysis; ALS |
C12H7MnO5 (cr) + 1.5 (g) =
(g) +
(cr) + 5
(g)
By formula: C12H7MnO5 (cr) + 1.5Br2 (g) = C7H7Br (g) + Br2Mn (cr) + 5CO (g)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -194.5 ± 7.8 | kJ/mol | HAL-HFC | Connor, Zafarani-Moattar, et al., 1982 | MS |
By formula: C7H7Br + 0.5H2 = C7H8 + 0.5Br2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -4. ± 2. | kJ/mol | Chyd | Ashcroft, Carson, et al., 1963 | liquid phase; ALS |
+ C4H9Li =
+
By formula: C7H7Br + C4H9Li = C11H16 + BrLi
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -338. ± 11. | kJ/mol | Cm | Fowell and Mortimer, 1961 | liquid 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SE-30 | 1087. | Krasnykh, Vasiltsova, et al., 2002 | Nitrogen, 30. C @ 5. min, 10. K/min; Column length: 25. m; Tend: 250. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 1059. | Zenkevich and Chupalov, 1996 | Program: not specified |
Capillary | DB-1 | 1061. | Hathcock and Bertsch, 1993 | 100. 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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas Chromatography, References
- Symbols used in this document:
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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