Butane, 2-bromo-
- Formula: C4H9Br
- Molecular weight: 137.018
- 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 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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
Spectrum
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Additional Data
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Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 164 |
NIST MS number | 227728 |
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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Squalane | 27. | 660. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 666. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 670. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 674. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Apiezon L | 130. | 703. | von Kováts, 1958 | Celite (40:60 Gewichtsverhaltnis) |
Packed | Apiezon L | 70. | 692. | von Kováts, 1958 | Celite (40:60 Gewichtsverhaltnis) |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | Carbowax 20M | 100. | 900. | Castello and D'Amato, 1985 | He, Chromosorb W AW DMCS; Column length: 3. m |
Packed | Carbowax 20M | 125. | 913. | Castello and D'Amato, 1985 | He, Chromosorb W AW DMCS; Column length: 3. m |
Packed | Carbowax 20M | 75. | 890. | Castello and D'Amato, 1985 | He, Chromosorb W AW DMCS; Column length: 3. m |
Normal alkane RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | Apiezon L | 130. | 689. | Arruda, Junkes, et al., 2008 |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 674. | Zenkevich and Marinichev, 2001 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 673. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 905. | Peng, Yang, et al., 1991 | Program: not specified |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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]
Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E.,
Variation of the retention index with temperature on squalane substrates,
J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203
. [all data]
von Kováts, 1958
von Kováts, E.,
206. Gas-chromatographische Charakterisierung organischer Verbindungen. Teil 1: Retentionsindices aliphatischer Halogenide, Alkohole, Aldehyde und Ketone,
Helv. Chim. Acta, 1958, 41, 7, 1915-1932, https://doi.org/10.1002/hlca.19580410703
. [all data]
Castello and D'Amato, 1985
Castello, G.; D'Amato, G.,
Gas Chromatography Separation and Identification of Linear and Branched-Chain Alkyl Bromides,
J. Chromatogr., 1985, 324, 363-371, https://doi.org/10.1016/S0021-9673(01)81335-2
. [all data]
Arruda, Junkes, et al., 2008
Arruda, A.C.S.; Junkes, B. da.S.; Souza, E.S.; Yunes, R.A.; Heizen, V.E.F.,
Semi-Emlirical Topological Index to Predict Properties of Halogenated Aliphatic Compounds,
J. Chemometrics, 2008, 22, 3-4, 186-194, https://doi.org/10.1002/cem.1121
. [all data]
Zenkevich and Marinichev, 2001
Zenkevich, I.G.; Marinichev, A.N.,
Comparison of Topological and Dynamics Molecular Characteristics for Precalculation of Chromatographic Retention Parameters of Organic Compounds (in Russian),
Zh. Struct. Khim., 2001, 42, 5, 893-902. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Peng, Yang, et al., 1991
Peng, C.T.; Yang, Z.C.; Ding, S.F.,
Prediction of rentention idexes. II. Structure-retention index relationship on polar columns,
J. Chromatogr., 1991, 586, 1, 85-112, https://doi.org/10.1016/0021-9673(91)80028-F
. [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, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, 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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