Butane, 1-bromo-
- Formula: C4H9Br
- Molecular weight: 137.018
- IUPAC Standard InChIKey: MPPPKRYCTPRNTB-UHFFFAOYSA-N
- CAS Registry Number: 109-65-9
- 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: n-Butyl bromide; Butyl bromide; 1-Bromobutane; n-C4H9Br; UN 1126
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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -35.4 | kcal/mol | Cm | Holm, 1973 | Grignard Rx; ALS |
ΔfH°liquid | -34.36 ± 0.31 | kcal/mol | Ccr | Bjellerup, 1961 | Reanalyzed by Cox and Pilcher, 1970, Original value = -34.47 ± 0.31 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -649.26 ± 0.30 | kcal/mol | Ccr | Bjellerup, 1961 | Reanalyzed by Cox and Pilcher, 1970, Original value = -649.17 ± 0.30 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 78.160 | cal/mol*K | N/A | Deese, 1931 | Extrapolation below 100 K, 42.84 J/mol*K.; DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
38.77 | 298.15 | Shehatta, 1993 | DH |
36.09 | 298. | Kurbatov, 1948 | T = 13 to 100°C, mean Cp, two temperatures.; DH |
36.379 | 292.3 | Deese, 1931 | T = 94 to 293 K. Value is unsmoothed experimental datum.; DH |
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 374. ± 2. | K | AVG | N/A | Average of 15 out of 16 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 385.4 | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 160.7 | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 160.8 | K | N/A | Timmermans, 1934 | Uncertainty assigned by TRC = 0.4 K; TRC |
Tfus | 160.4 | K | N/A | Deese, 1931, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tfus | 160.75 | K | N/A | Timmermans, 1921 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 577.5 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.74 ± 0.06 | kcal/mol | AVG | N/A | Average of 7 values; Individual data points |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
7.770 | 374.7 | N/A | Majer and Svoboda, 1985 | |
8.27 | 353. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 338. to 373. K. See also Svoboda, Majer, et al., 1977.; AC |
8.96 | 288. | A,EST | Stephenson and Malanowski, 1987 | Based on data from 273. to 400. K. See also Li and Rossini, 1961 and Dykyj, 1971.; AC |
8.51 ± 0.02 | 322. | C | Svoboda, Majer, et al., 1977 | AC |
8.34 ± 0.02 | 332. | C | Svoboda, Majer, et al., 1977 | AC |
8.25 ± 0.02 | 339. | C | Svoboda, Majer, et al., 1977 | AC |
8.05 ± 0.02 | 352. | C | Svoboda, Majer, et al., 1977 | AC |
7.89 ± 0.02 | 366. | C | Svoboda, Majer, et al., 1977 | AC |
7.78 | 372.4 | V | Mathews and Fehlandt, 1931 | ALS |
8.01 | 308. | N/A | Smyth and Engel, 1929 | Based on data from 293. to 343. K. See also Boublik, Fried, et al., 1984.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kcal/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kcal/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
298. to 366. | 12.16 | 0.2641 | 577.5 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
195.18 to 295.82 | 3.45456 | 1105.883 | -65.203 | Milazzo, 1956 | Coefficents calculated by NIST from author's data. |
293. to 343. | 3.79436 | 1084.887 | -65.244 | Smyth and Engel, 1929 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.21 | 160.4 | Domalski and Hearing, 1996 | AC |
2.207 | 160.4 | Deese, 1931 | DH |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.76 | 160.4 | Domalski and Hearing, 1996 | CAL |
13.76 | 160.4 | Deese, 1931 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Mass spectrum (electron ionization), References, Notes
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) | 10.13 ± 0.02 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.11 | EST | Luo and Pacey, 1992 | LL |
10.12 | PE | Kimura, Katsumata, et al., 1981 | LLK |
10.15 | PE | Kimura, Katsumata, et al., 1973 | LLK |
10.13 ± 0.015 | PE | Hashmall and Heilbronner, 1970 | RDSH |
10.13 ± 0.01 | PI | Watanabe, 1957 | RDSH |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References, Notes
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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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 | CONTINENTAL OIL CO., PONCA CITY, OKLAHOMA, USA |
NIST MS number | 58817 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Bjellerup, 1961
Bjellerup, L.,
Heats of combustion and formation of the 1-bromoalkanes from C4 through C8,
Acta Chem. Scand., 1961, 15, 231-241. [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]
Deese, 1931
Deese, R.F., Jr.,
Thermal energy studies. IV. Comparison of continuous and discontinuous methods of measuring heat capacities. Heat capacities of some alphatic bromides,
J. Am. Chem. Soc., 1931, 53, 3673-3683. [all data]
Shehatta, 1993
Shehatta, I.,
Heat capacity at constant pressure of some halogen compounds,
Thermochim. Acta, 1993, 213, 1-10. [all data]
Kurbatov, 1948
Kurbatov, V.Ya.,
Heat capacity of liquids. 2. Heat capacity and the temperature dependence of heat capacity from halogen derivatives of acylic hydrocarbons,
Zh. Obshch. Kim., 1948, 18, 372-389. [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]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]
Timmermans, 1934
Timmermans, J.,
Theory of Concentrated Solutions XII.,
Bull. Soc. Chim. Belg., 1934, 43, 626. [all data]
Deese, 1931, 2
Deese, R.F.,
Thermal energy studies: IV comparison of continuous and discontinuous methods of measuring heat capacities heat capacities of some aliphatic bromides,
J. Am. Chem. Soc., 1931, 53, 3673. [all data]
Timmermans, 1921
Timmermans, J.,
The Freezing Points of Organic Substances IV. New Exp. Determinations,
Bull. Soc. Chim. Belg., 1921, 30, 62. [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]
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]
Svoboda, Majer, et al., 1977
Svoboda, V.; Majer, V.; Veselý, F.; Pick, J.,
Heats of vaporization of alkyl bromides,
Collect. Czech. Chem. Commun., 1977, 42, 6, 1755-1760, https://doi.org/10.1135/cccc19771755
. [all data]
Li and Rossini, 1961
Li, J.C.M.; Rossini, F.D.,
Vapor Pressures and Boiling Points of the l-Fluoroalkanes, l-Chloroalkanes, l-Bromoalkanes, and l-Iodoalkanes, C 1 to C 20 .,
J. Chem. Eng. Data, 1961, 6, 2, 268-270, https://doi.org/10.1021/je60010a025
. [all data]
Dykyj, 1971
Dykyj, J.,
Petrochemia, 1971, 11, 2, 27. [all data]
Mathews and Fehlandt, 1931
Mathews, J.H.; Fehlandt, P.R.,
The heats of vaporization of some organic compounds,
J. Am. Chem. Soc., 1931, 53, 3212-32. [all data]
Smyth and Engel, 1929
Smyth, C.P.; Engel, E.W.,
MOLECULAR ORIENTATION AND THE PARTIAL VAPOR PRESSURES OF BINARY MIXTURES. I. SYSTEMS COMPOSED OF NORMAL LIQUIDS,
J. Am. Chem. Soc., 1929, 51, 9, 2646-2660, https://doi.org/10.1021/ja01384a006
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Milazzo, 1956
Milazzo, G.,
Tensioni di Vapore di Alcune Sostanze Organiche a Bassa Temperatura,
Ann. Chim. (Rome), 1956, 46, 1105-1111. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
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]
Kimura, Katsumata, et al., 1973
Kimura, K.; Katsumata, S.; Achiba, Y.; Matsumoto, H.; Nagakura, S.,
Photoelectron spectra and orbital structures of higher alkyl chlorides, bromides, and iodides.,
Bull. Chem. Soc. Jpn., 1973, 46, 373. [all data]
Hashmall and Heilbronner, 1970
Hashmall, J.A.; Heilbronner, E.,
n-Ionization potentials of alkyl bromides,
Angew. Chem. Intern. Ed., 1970, 9, 305. [all data]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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