Butane, 2-bromo-

• Formula: C₄H₉Br
• Molecular weight: 137.018
• IUPAC Standard InChI: InChI=1S/C4H9Br/c1-3-4(2)5/h4H,3H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: UPSXAPQYNGXVBF-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • 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
  • References
  • Notes
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

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

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

Enthalpy of vaporization

Enthalpy of fusion

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

 +  =

By formula: HBr + C₄H₈ = C₄H₉Br

 +  =

By formula: HBr + C₄H₈ = C₄H₉Br

=

By formula: C₄H₉Br = C₄H₉Br

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

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% CCl4 FOR 3800-1340, 10% CS2 FOR 1340-430); DOW KBr FOREPRISM-GRATING $$SPECTRAL CONTAMINATION DUE TO CS2 AROUND 850 AND CCl4 AROUND 1550 CM^-1 HAVE BEEN SUBTRACTED; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

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

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

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Kovats' RI, polar column, isothermal

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Normal alkane RI, non-polar column, isothermal

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

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Normal alkane RI, polar column, custom temperature program

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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, 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, 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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