Butane, 2-bromo-
- Formula: C4H9Br
- Molecular weight: 137.018
- IUPAC Standard InChI: InChI=1S/C4H9Br/c1-3-4(2)5/h4H,3H2,1-2H3
- IUPAC Standard InChIKey: UPSXAPQYNGXVBF-UHFFFAOYSA-N
- CAS Registry Number: 78-76-2
- 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: sec-Butyl Bromide; Methylethylbromomethane; 2-Bromobutane; 2-Butyl bromide; (+/-)-2-Bromobutane; sec-C4H9Br; UN 2339
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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 | -120. ± 2. | kJ/mol | Ccr | Bjellerup, 1961 |
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 | -156. | kJ/mol | Cm | Holm, 1973 | Grignard Rx |
| ΔfH°liquid | -155.3 ± 1.3 | kJ/mol | Ccr | Bjellerup, 1961 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2705. ± 1. | kJ/mol | Ccr | Bjellerup, 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 | 364. ± 1. | K | AVG | N/A | Average of 8 values; Individual data points |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 160.50 | K | N/A | Dreisbach, 1955 | Uncertainty assigned by TRC = 0.02 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 34.51 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
| ΔvapH° | 34.5 ± 0.1 | kJ/mol | C | Wadsö, Luoma, et al., 1968 | AC |
| ΔvapH° | 34.47 ± 0.06 | kJ/mol | C | Wadso, 1968 | ALS |
| ΔvapH° | 34.8 ± 0.1 | kJ/mol | C | Wadsö, Murto, et al., 1966 | AC |
| ΔvapH° | 34.4 ± 0.08 | kJ/mol | C | Wadso, 1966 | ALS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 30.77 | 364.5 | N/A | Majer and Svoboda, 1985 | |
| 33.9 | 296. | A | Stephenson and Malanowski, 1987 | Based on data from 281. to 403. K. See also Dykyj, 1971.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 6.88 | 160.3 | Acree, 1991 | 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 by: 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
+
=
By formula: HBr + C4H8 = C4H9Br
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -77.07 ± 0.50 | kJ/mol | Cm | Lacher, Billings, et al., 1952 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -76.8 ± 6.6 kJ/mol; Heat of Hydrobromination at 373 K |
+
=
By formula: HBr + C4H8 = C4H9Br
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -72.22 ± 0.50 | kJ/mol | Cm | Lacher, Billings, et al., 1952 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -72.6 ± 5.6 kJ/mol; Heat of hydrobromination at 373 K |
+
=
By formula: HBr + C4H8 = C4H9Br
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -83.85 ± 0.50 | kJ/mol | Cm | Lacher, Billings, et al., 1952 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -84.3 ± 7.5 kJ/mol; Heat of hydrobromination at 367 K |
=
By formula: C4H9Br = C4H9Br
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -10. | kJ/mol | Eqk | Alenin, Rozhnov, et al., 1974 | liquid phase; Heat of isomerization |
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:
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 10.01 ± 0.02 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.03 | EST | Luo and Pacey, 1992 | LL |
| 10.00 | PI | Traeger, 1981 | LLK |
| 10.04 | PE | Kimura, Katsumata, et al., 1981 | LLK |
| 9.98 ± 0.01 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C4H9+ | 10.23 | Br | PI | Traeger, 1981 | LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Bjellerup, 1961
Bjellerup, L.,
On the accuracy of heat of combustion data obtained with a precision moving-bomb calorimetric method for organic bromine compounds,
Acta Chem. Scand., 1961, 15, 121-140. [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]
Dreisbach, 1955
Dreisbach, R.R.,
Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [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]
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]
Wadsö, Murto, et al., 1966
Wadsö, Ingemar; Murto, Maija-Leena; Bergson, Göran; Ehrenberg, L.; Brunvoll, J.; Bunnenberg, E.; Djerassi, Carl; Records, Ruth,
Heats of Vaporization for a Number of Organic Compounds at 25 degrees C.,
Acta Chem. Scand., 1966, 20, 544-552, https://doi.org/10.3891/acta.chem.scand.20-0544
. [all data]
Wadso, 1966
Wadso, I.,
Acta Chem. Scand., 1966, 20, 544. [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, 1971
Dykyj, J.,
Petrochemia, 1971, 11, 2, 27. [all data]
Acree, 1991
Acree, William E.,
Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation,
Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H
. [all data]
Lacher, Billings, et al., 1952
Lacher, J.R.; Billings, T.J.; Campion, D.E.,
Vapor phase heats of hydrobromination of the isomeric butenes,
J. Am. Chem. Soc., 1952, 74, 5291-52. [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]
Alenin, Rozhnov, et al., 1974
Alenin, V.I.; Rozhnov, A.M.; Nesterova, T.N.; Strizhkov, V.N.,
Equilibrium in the isomerisation of liquid C3-C4 monobromoalkanes,
Russ. J. Phys. Chem. (Engl. Transl.), 1974, 48, 1702. [all data]
Luo and Pacey, 1992
Luo, Y.-R.; Pacey, P.D.,
Effects of alkyl substitution on ionization energies of alkanes and haloalkanes and on heats of formation of their molecular cations. Part 2. Alkanes and chloro-, bromo- and iodoalkanes,
Int. J. Mass Spectrom. Ion Processes, 1992, 112, 63. [all data]
Traeger, 1981
Traeger, J.C.,
Heat of formation of sec-butyl cation in the gas phase,
Org. Mass Spectrom., 1981, 16, 193. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J.,
Ionization potentials of some molecules,
J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion 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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