Methane, bromo-

• Formula: CH₃Br
• Molecular weight: 94.939
• IUPAC Standard InChI: InChI=1S/CH3Br/c1-2/h1H3 Copy

  
• IUPAC Standard InChIKey: GZUXJHMPEANEGY-UHFFFAOYSA-N Copy
• CAS Registry Number: 74-83-9
• 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.
• Isotopologues:
  • bromo(2H3)methane
• Other names: Bromomethane; Curafume; Embafume; Halon 1001; Haltox; Iscobrome; Methyl bromide; Monobromomethane; Terabol; CH3Br; Bercema; Brom-methan; Brom-O-gas; Brom-O-gaz; Bromometano; Bromure de methyle; Bromuro di metile; Broommethaan; Celfume; Dawson 100; Detia gas ex-M; Dowfume mc-2; Dowfume mc-33; Dowfume mc-2 soil fumigant; Edco; Fumigant-1; Kayafume; MBX; MeBr; Metafume; Methogas; Methylbromid; Metylu bromek; Pestmaster; Profume; R 40B1; Rcra waste number U029; Terr-O-gas 67; Terr-O-gas 100; UN 1062; Zytox; Brom-O-sol; Methybrom
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Ion clustering data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
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

Enthalpy of vaporization

Entropy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
MS - José A. Martinho Simões
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

CH₂Br^- +  =

By formula: CH₂Br^- + H⁺ = CH₃Br

 +  = ( • )

By formula: Cl^- + CH₃Br = (Cl^- • CH₃Br)

 +  = ( • )

By formula: Br^- + CH₃Br = (Br^- • CH₃Br)

 (cr) +  (l) = CH₃BrMg (solution)

By formula: Mg (cr) + CH₃Br (l) = CH₃BrMg (solution)

 +  = ( • )

By formula: CH₃⁺ + CH₃Br = (CH₃⁺ • CH₃Br)

 +  = ( • )

By formula: I^- + CH₃Br = (I^- • CH₃Br)

 (l) + 3 (l) = Br₃In (cr) + 3 (g)

By formula: C₃H₉In (l) + 3Br₂ (l) = Br₃In (cr) + 3CH₃Br (g)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + CH₃Br = (CH₆N⁺ • CH₃Br)

 (l) + 2 (l) = 2 (g) +  (cr)

By formula: C₂H₆Hg (l) + 2Br₂ (l) = 2CH₃Br (g) + Br₂Hg (cr)

 (l) +  (g) = C₃H₉BrSn (l) +  (g)

By formula: C₄H₁₂Sn (l) + Br₂ (g) = C₃H₉BrSn (l) + CH₃Br (g)

 (cr) + 1.5 (g) =  (cr) + 5 (g) +  (g)

By formula: C₆H₃MnO₅ (cr) + 1.5Br₂ (g) = Br₂Mn (cr) + 5CO (g) + CH₃Br (g)

 (cr) + 1.5 (g) =  (cr) + 6 (g) +  (g)

By formula: C₇H₃MnO₆ (cr) + 1.5Br₂ (g) = Br₂Mn (cr) + 6CO (g) + CH₃Br (g)

 + 2 = 2 + 

By formula: H₂ + 2CH₃Br = 2CH₄ + Br₂

 +  =  + 

By formula: H₂ + CH₃Br = HBr + CH₄

 +  =  + 

By formula: CH₄ + Br₂ = HBr + CH₃Br

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to CH₃Br⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

CH₂Br^- +  =

By formula: CH₂Br^- + H⁺ = CH₃Br

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (100 mmHg DILUTED TO A TOTAL PRESSURE OF 600 mmHg WITH N2); DOW KBr FOREPRISM; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

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

• gas

Data compiled by: Pamela M. Chu, Franklin R. Guenther, George C. Rhoderick, and Walter J. Lafferty

• gas; IFS66V (Bruker); 3-Term B-H Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Boxcar Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Happ Genzel Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); NB Strong Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution
• gas; IFS66V (Bruker); Triangular Apodization
  0.1250, 0.2410, 0.4820, 0.9640, 1.9290 cm^-1 resolution

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

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   C_3ν     Symmetry Number σ = 3

Source: Shimanouchi, 1972

Notes

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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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-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, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Ferguson, Okafo, et al., 1973
Ferguson, K.C.; Okafo, E.N.; Whittle, E., Bond dissociation energies from equilibrium studies Part 4.-The equilibrium Br₂ + CH₄ = HBr + CH₃Br. Determination of D(CH₃-Br) and ΔH_f°(CH₃Br,g), J. Chem. Soc. Faraday Trans. 1, 1973, 69, 295-301. [all data]

Adams, Carson, et al., 1966
Adams, G.P.; Carson, A.S.; Laye, P.G., Thermochemistry of reductions caused by lithium aluminium hydride. Part 4.-Heat of formation of methyl bromide, Trans. Faraday Soc., 1966, 62, 1447-1449. [all data]

Fowell, Lacher, et al., 1965
Fowell, P.; Lacher, J.R.; Park, J.D., Reaction heats of organic compounds. Part 3.-Heats of hydrogenation of methyl bromide and ethyl bromide, Trans. Faraday Soc., 1965, 61, 1324-1327. [all data]

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Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Egan and Kemp, 1938
Egan, C.J.; Kemp, J.D., Methyl bromide. The heat capacity, vapor pressure, heats of transition, fusion and vaporization. Entropy and density of the gas, J. Am. Chem. Soc., 1938, 60, 2097-2101. [all data]

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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]

Farchan Laboratories, 1990
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Majer and Svoboda, 1985
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McKenna, F.E.; Tartar, H.V.; Lingafelter, E.C., Studies of hemiacetal formation in alcohol - aldehyde systems: II refraction studies, J. Am. Chem. Soc., 1953, 75, 604-7. [all data]

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Egan, C.J.; Kemp, J.D., Methyl Bromide. The Heat Capacity, Vapor Pressure, Heats of Trans- ition, Fusion and Vaporization. Entropy and Density of the Gas, J. Am. Chem. Soc., 1938, 60, 2097. [all data]

Beersmans and Jungers, 2010
Beersmans, J.; Jungers, J.C., Synthèse et Étude des Chlorure, Bromure et Iodure de Deutérométhyle, Bull. Soc. Chim. Belges, 2010, 56, 5-8, 238-250, https://doi.org/10.1002/bscb.19470560506 . [all data]

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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]

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Egan, C.J.; Kemp, J.D., Methyl bromide. The heat capacity, vapor pressure, heats of transition, fusion and vaporization. Entropy and density of the gas, J. Am. Chem. Soc., 1938, 60, 2097-21. [all data]

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Beersmans, J.; Jungers, J.C., Synthese et Etude des Chlorure, Bromure et Iodure de Deuteromethyle, Bull. Soc. Chim. Belg., 1947, 56, 5-8, 238-250, https://doi.org/10.1002/bscb.19470560506 . [all data]

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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]

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Hierl, Henchman, et al., 1992
Hierl, P.M.; Henchman, M.J.; Paulson, J.F., Threshold Energies for the Reactions HO- + MeX - MeOH + X- measured by Tandem Mass Spectrometry: Acidities of MeCl and MeBr, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 475, https://doi.org/10.1016/0168-1176(92)80109-E . [all data]

Ingemann and Nibbering, 1985
Ingemann, S.; Nibbering, N.M.M., Gas phase chemistry of alpha-thio carbanions, Can. J. Chem., 1985, 62, 2273. [all data]

Rogers, Simpson, et al., 2010
Rogers, N.J.; Simpson, M.J.; Tuckett, R.P.; Dunn, K.F.; Latimer, C.J., Vacuum-UV negative photoion spectroscopy of CH3F, CH3Cl and CH3Br, Phys. Chem. Chem. Phys., 2010, 12, 36, 10971-10980, https://doi.org/10.1039/c0cp00234h . [all data]

Ingemann and Nibbering, 1985, 2
Ingemann, S.; Nibbering, N.M.M., Gas-phase acidity of CH₃X [X = P(CH₃)₂, SCH₃, F, Cl, Br, I] compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 837. [all data]

Li, Ross, et al., 1996
Li, C.; Ross, P.; Szulejko, J.; McMahon, T.B., High-Pressure Mass Spectrometric Investigations of the Potential Energy Surfaces of Gas-Phase Sn2 Reactions., J. Am. Chem. Soc., 1996, 118, 39, 9360, https://doi.org/10.1021/ja960565o . [all data]

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Dougherty, R.C.; Roberts, J.D., SN₂ reactions in the gas phase. Nucleophilicity effects, Org. Mass Spectrom., 1974, 8, 81. [all data]

Riveros, Breda, et al., 1973
Riveros, J.M.; Breda, A.C.; Blair, L.K., Formation and relative stability of chloride ion clusters in the gas phase by ICR spectroscopy, J. Am. Chem. Soc., 1973, 95, 4066. [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Fluoride and chloride affinities of main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of lewis acidities from ion cyclotron resonance halide-exchange equilibria, J. Phys. Chem., 1984, 88, 1083. [all data]

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McMahon, Heinis, et al., 1988
McMahon, T.; Heinis, T.; Nicol, G.; Hovey, J.K.; Kebarle, P., Methyl Cation Affinities, J. Am. Chem. Soc., 1988, 110, 23, 7591, https://doi.org/10.1021/ja00231a002 . [all data]

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Van Duzor, Wei, et al., 2010
Van Duzor, M.; Wei, J.; Mbaiwa, F.; Mabbs, R., I-center dot CH3X (X=Cl, Br, I) photodetachment: The effect of electron-molecule interactions in cluster anion photodetachment spectra and angular distributions, J. Chem. Phys., 2010, 133, 14, 144303, https://doi.org/10.1063/1.3487739 . [all data]

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Cyr, D.M.; Bishea, G.A.; Scarton, M.G.; Johnson, M.A., Observation of Charge-Transfer Excited States in the I-.CH3I, I-.CH3Br, and I-.CH2Br2 S(N)2 Reaction Intermediates Using Photofragmentation, J. Chem. Phys., 1992, 97, 8, 5911, https://doi.org/10.1063/1.463752 . [all data]

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Pedley, J.B.; Rylance, J., Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brigton, 1977. [all data]

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Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds in Academic Press, New York, 1970. [all data]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Hartley, Pritchard, et al., 1950
Hartley, K.; Pritchard, H.O.; Skinner, H.A., Thermochemistry of metallic alkyls. III.?mercury dimethyl and mercury methyl halides, Trans. Faraday Soc., 1950, 46, 1019, https://doi.org/10.1039/tf9504601019 . [all data]

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Pedley, J.B.; Skinner, H.A.; Chernick, C.L., Thermochemistry of metallic alkyls. Part 8.?Tin tetramethyl, and hexamethyl distannane, Trans. Faraday Soc., 1957, 53, 1612, https://doi.org/10.1039/tf9575301612 . [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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Baig, Connerade, et al., 1982
Baig, M.A.; Connerade, J.P.; Hormes, J., Autoionisation resonances in the 4p(Π) spectrum of methyl bromide, J. Phys. B:, 1982, 15, 5. [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]

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Kaposi, O.; Riedel, M.; Vass-Balthazar, K.; Sanchez, G.R.; Lelik, L., Mass-spectrometric determination of thermochemical data of CHBr₃ and CBr₄ by study of their electron impact and heterogeneous pyrolytic decompositions, Acta Chim. Acad. Sci. Hung., 1976, 89, 221. [all data]

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Kaposi, Riedel, et al., 1975
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Hochmann, Templet, et al., 1975
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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Vibrational and/or electronic energy levels, Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Ttriple	Triple point temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization

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