Methane, dibromo-
- Formula: CH2Br2
- Molecular weight: 173.835
- IUPAC Standard InChIKey: FJBFPHVGVWTDIP-UHFFFAOYSA-N
- CAS Registry Number: 74-95-3
- 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: Dibromomethane; Methylene bromide; Methylene dibromide; CH2Br2; Rcra waste number U068; UN 2664
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Vibrational and/or electronic energy levels, Gas Chromatography, 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:
B - John E. Bartmess
MS - José A. Martinho Simões
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
CHBr2- + =
By formula: CHBr2- + H+ = CH2Br2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1544. ± 13. | kJ/mol | G+TS | Born, Ingemann, et al., 2000 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1512. ± 13. | kJ/mol | IMRB | Born, Ingemann, et al., 2000 | gas phase; B |
C14H21MnO2 (solution) + (solution) = C8H7Br2MnO2 (solution) +
(solution)
By formula: C14H21MnO2 (solution) + CH2Br2 (solution) = C8H7Br2MnO2 (solution) + C7H16 (solution)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -51.0 ± 5.0 | kJ/mol | PAC | Yang and Yang, 1992 | solvent: Heptane; MS |
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:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 10.41 ± 0.13 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.24 ± 0.02 | PI | Ma, Liao, et al., 1993 | LL |
10.5 ± 0.1 | EI | Kaposi, Riedel, et al., 1976 | LLK |
10.52 ± 0.05 | PI | Tsai, Baer, et al., 1975 | LLK |
10.49 ± 0.02 | PI | Watanabe, Nakayama, et al., 1962 | RDSH |
10.6 | PE | Von Niessen, Asbrink, et al., 1982 | Vertical value; LBLHLM |
9.78 | PE | Wittel and Bock, 1974 | Vertical value; LLK |
10.61 | PE | Dixon, Murrell, et al., 1971 | Vertical value; LLK |
10.61 | PE | Potts, Lempka, et al., 1970 | Vertical value; RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
Br+ | 15.5 ± 0.1 | CH2Br | EI | DeCorpo, Bafus, et al., 1971 | LLK |
Br+ | 16.0 | CH2Br | EI | Franklin and Haney, 1970 | RDSH |
HBr+ | 18.2 ± 0.2 | ? | EI | Kaposi, Riedel, et al., 1976 | LLK |
Br2+ | 20.7 ± 0.5 | ? | EI | Kaposi, Riedel, et al., 1976 | LLK |
C+ | 22.7 ± 0.5 | ? | EI | Kaposi, Riedel, et al., 1976 | LLK |
C+ | 24.52 ± 0.05 | ? | EI | Reed and Snedden, 1956 | RDSH |
CBr+ | 19.6 ± 0.3 | ? | EI | Kaposi, Riedel, et al., 1976 | LLK |
CBr2+ | 15.6 ± 0.5 | ? | EI | Kaposi, Riedel, et al., 1976 | LLK |
CH+ | 22.0 ± 0.5 | ? | EI | Kaposi, Riedel, et al., 1976 | LLK |
CH+ | 21.55 ± 0.05 | ? | EI | Reed and Snedden, 1956 | RDSH |
CHBr+ | 16.0 ± 0.5 | ? | EI | Kaposi, Riedel, et al., 1976 | LLK |
CH2+ | 17.1 ± 0.3 | ? | EI | Kaposi, Riedel, et al., 1976 | LLK |
CH2Br+ | 11.27 | Br | PI | Ma, Liao, et al., 1993 | LL |
CH2Br+ | 11.29 | Br | EI | Holmes, Lossing, et al., 1988 | LL |
CH2Br+ | 11.1 ± 0.2 | Br | EI | Kaposi, Riedel, et al., 1976 | LLK |
CH2Br+ | 11.35 ± 0.02 | Br | PI | Tsai, Baer, et al., 1975 | LLK |
CH2Br+ | 10.93 ± 0.04 | Br | EI | Reed and Snedden, 1956 | RDSH |
De-protonation reactions
CHBr2- + =
By formula: CHBr2- + H+ = CH2Br2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1544. ± 13. | kJ/mol | G+TS | Born, Ingemann, et al., 2000 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1512. ± 13. | kJ/mol | IMRB | Born, Ingemann, et al., 2000 | gas phase; B |
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: C2ν Symmetry Number σ = 2
Sym. | No | Approximate | Selected Freq. | Infrared | Raman | Comments | ||||
---|---|---|---|---|---|---|---|---|---|---|
Species | type of mode | Value | Rating | Value | Phase | Value | Phase | |||
a1 | 1 | CH2 s-str | 3009 | C | 3009 W | gas | 3008 | gas | ||
a1 | 2 | CH2 scis | 1382 | C | 1382 VW | gas | 1402 | gas | ||
a1 | 3 | CBr2 s-str | 588 | C | 588 M | gas | 584 | gas | ||
a1 | 4 | CBr2 scis | 169 | C | 169 | gas | ||||
a2 | 5 | CH2 twist | 1095 | D | ia | 1095 | liq. | |||
b1 | 6 | CH2 a-str | 3073 | B | 3073 VW | gas | 3064 | liq. | ||
b1 | 7 | CH2 rock | 812 | B | 812 M | gas | 813 | liq. | ||
b2 | 8 | CH2 wag | 1195 | B | 1195 VS | gas | 1195 | liq. | ||
b2 | 9 | CBr a-str | 653 | B | 653 VS | gas | 640 | gas | ||
Source: Shimanouchi, 1972
Notes
VS | Very strong |
M | Medium |
W | Weak |
VW | Very weak |
ia | Inactive |
B | 1~3 cm-1 uncertainty |
C | 3~6 cm-1 uncertainty |
D | 6~15 cm-1 uncertainty |
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 | OV-1 | 100. | 690. | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | OV-1 | 125. | 698. | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | OV-1 | 75. | 683. | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | Apolane | 70. | 681.7 | Riedo, Fritz, et al., 1976 | He, Chromosorb; Column length: 2.4 m |
Packed | Squalane | 27. | 653. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 49. | 660. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 67. | 666. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Packed | Squalane | 86. | 671. | Hively and Hinton, 1968 | He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | PEG-40M | 120. | 1166. | Grigor'eva, Vasil'ev, et al., 1993 | 40. m/0.25 mm/0.10 μm, Ar |
Packed | SP-1000 | 100. | 1189.98 | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | SP-1000 | 125. | 1196.47 | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | SP-1000 | 75. | 1175.95 | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 672.2 | Helmig, Pollock, et al., 1996 | 30. m/0.25 mm/1. μm, 6. K/min; Tstart: -50. C; Tend: 180. C |
Capillary | SE-54 | 700. | Weber, 1986 | 25. m/0.31 mm/0.17 μm, H2, 2. K/min; Tstart: 35. C |
Capillary | SE-54 | 700. | Weber, 1986 | 25. m/0.31 mm/0.17 μm, H2, 2. K/min; Tstart: 35. C |
Capillary | SE-54 | 704. | Weber, 1986 | 25. m/0.31 mm/0.17 μm, H2, 2. K/min; Tstart: 35. C |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Supelcowax-10 | 1174. | Matiella and Hsieh, 1990 | 60. m/0.25 mm/0.25 μm, 40. C @ 5. min, 2. K/min, 175. C @ 20. min |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-1 | 696. | Peters, de Leer, et al., 1994 | 25. m/0.2 mm/0.33 μm, He, 50. C @ 5. min, 8. K/min, 300. C @ 10. min |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | SPB-1 | 683. | Flanagan, Streete, et al., 1997 | 60. m/0.53 mm/5. μm, He; Program: 40C(6min) => 5C/min => 80C => 10C/min => 200C |
Capillary | DB-5 | 708. | Sorimachi, Tanabe, et al., 1995 | He; Column length: 30. m; Program: not specified |
Capillary | SPB-1 | 683. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: 40 0C (6 min) 5 0C/min -> 80 0C 10 0C/min -> 200 0C |
Capillary | SPB-1 | 733. | Strete, Ruprah, et al., 1992 | 60. m/0.53 mm/5.0 μm, Helium; Program: not specified |
Normal alkane RI, polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Carbowax 20M | 1185. | Ramsey and Flanagan, 1982 | Program: not specified |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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.
Born, Ingemann, et al., 2000
Born, M.; Ingemann, S.; Nibbering, N.M.M.,
Thermochemical properties of halogen-substituted methanes, methyl radicals, and carbenes in the gas phase,
Int. J. Mass Spectrom., 2000, 194, 2-3, 103-113, https://doi.org/10.1016/S1387-3806(99)00125-6
. [all data]
Yang and Yang, 1992
Yang, P.-F.; Yang, K.G.,
J. Am. Chem. Soc., 1992, 114, 6937. [all data]
Ma, Liao, et al., 1993
Ma, Z.-X.; Liao, C.-L.; Ng, C.Y.; Ma, N.G.; Li, W.-K.,
Adiabatic ionization energy and electron affinity of CH2Br,
J. Chem. Phys., 1993, 99, 6470. [all data]
Kaposi, Riedel, et al., 1976
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]
Tsai, Baer, et al., 1975
Tsai, B.P.; Baer, T.; Werner, A.S.; Lin, S.F.,
A photoelectron-photoion coincidence study of the ionization and fragment appearance potentials of bromo- and iodomethanes,
J. Phys. Chem., 1975, 79, 570. [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]
Von Niessen, Asbrink, et al., 1982
Von Niessen, W.; Asbrink, L.; Bieri, G.,
30.4 nm He(II) Photoelectron spectra of organic molecules. Part VI. Halogeno-compounds (C,H,X: X = Cl, Br, I),
J. Electron Spectrosc. Relat. Phenom., 1982, 26, 173. [all data]
Wittel and Bock, 1974
Wittel, K.; Bock, H.,
Photoelektronenspekten und molekuleigenschaften. XXVII. Chlor- und bromathylene- beispiele fur anderungen in π- und σ-Systemen,
Chem. Ber., 1974, 107, 317. [all data]
Dixon, Murrell, et al., 1971
Dixon, R.N.; Murrell, J.N.; Narayan, B.,
The photoelectron spectra of the halomethanes,
Mol. Phys., 1971, 20, 611. [all data]
Potts, Lempka, et al., 1970
Potts, A.W.; Lempka, H.J.; Streets, D.G.; Price, W.C.,
Photoelectron spectra of the halides of elements in groups III, IV, V and VI,
Phil. Trans. Roy. Soc. (London), 1970, A268, 59. [all data]
DeCorpo, Bafus, et al., 1971
DeCorpo, J.J.; Bafus, D.A.; Franklin, J.L.,
Enthalpies of formation of the monohalomethyl radicals from mass spectrometric studies of the dihalomethanes,
J. Chem. Thermodyn., 1971, 3, 125. [all data]
Franklin and Haney, 1970
Franklin, J.L.; Haney, M.A.,
Energy distribution in ionic decomposition processes, Recent Developments in Mass Spectroscopy, ed. K. Ogata and T. Hayakawa Baltimore Univ. Park Press, Baltimore, MD, 1970, 909. [all data]
Reed and Snedden, 1956
Reed, R.I.; Snedden, W.,
Studies in electron impact methods. Part 6.-The formation of the methine and carbon ions,
J. Chem. Soc. Faraday Trans., 1956, 55, 876. [all data]
Holmes, Lossing, et al., 1988
Holmes, J.L.; Lossing, F.P.; McFarlane, R.A.,
Stabilization energy and positional effects in halogen-substituted alkyl ions.,
Int. J. Mass Spectrom. Ion Phys., 1988, 86, 209. [all data]
Shimanouchi, 1972
Shimanouchi, T.,
Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]
Castello and Gerbino, 1988
Castello, G.; Gerbino, T.C.,
Effect of Temperature on the Gas Chromatographic Separation of Halogenated Compounds on Polar and Non-Polar Stationary Phases,
J. Chromatogr., 1988, 437, 33-45, https://doi.org/10.1016/S0021-9673(00)90369-8
. [all data]
Riedo, Fritz, et al., 1976
Riedo, F.; Fritz, D.; Tarján, G.; Kováts, E.Sz.,
A tailor-made C87 hydrocarbon as a possible non-polar standard stationary phase for gas chromatography,
J. Chromatogr., 1976, 126, 63-83, https://doi.org/10.1016/S0021-9673(01)84063-2
. [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]
Grigor'eva, Vasil'ev, et al., 1993
Grigor'eva, D.N.; Vasil'ev, A.V.; Golovnya, R.V.,
Effect of the temperature on the retention indices in homologous series of bifunctional compounds under capillary gas chromatography conditions,
J. Anal. Chem. USSR (Engl. Transl.), 1993, 48, 7, 817-822. [all data]
Helmig, Pollock, et al., 1996
Helmig, D.; Pollock, W.; Greenberg, J.; Zimmerman, P.,
Gas chromatography mass spectrometry analysis of volatile organic trace gases at Mauna Loa Observatory, Hawaii,
J. Geophys. Res., 1996, 101, D9, 14697-14710, https://doi.org/10.1029/96JD00212
. [all data]
Weber, 1986
Weber, L.,
Utilization of the Sadtler standard RI system in micropollution analyses,
J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 8, 446-451, https://doi.org/10.1002/jhrc.1240090806
. [all data]
Matiella and Hsieh, 1990
Matiella, J.E.; Hsieh, T.C.-Y.,
Analysis of crabmeat volatile compounds,
J. Food Sci., 1990, 55, 4, 962-966, https://doi.org/10.1111/j.1365-2621.1990.tb01575.x
. [all data]
Peters, de Leer, et al., 1994
Peters, R.J.D.; de Leer, E.W.B.; Versteegh, J.F.M.,
Identification of Halogenated Compounds Produced by Chlorination of Humic Acid in the Presence of Bromide,
J. Chromatogr. A, 1994, 686, 2, 253-261, https://doi.org/10.1016/0021-9673(94)00719-5
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Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D.,
Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technicalseries1997-01-011.pdf. [all data]
Sorimachi, Tanabe, et al., 1995
Sorimachi, J.; Tanabe, A.; Mitobe, H.; Kuniaki, K.; Masaaki, S.,
Programmed temperature retention indices for volatile organic compounds on headspace GC/MS analysis,
Niigata-ken Eisei Kogai Kenkyusho Nenpo, 1995, 11, 75-79. [all data]
Strete, Ruprah, et al., 1992
Strete, P.J.; Ruprah, M.; Ramsey, J.D.; Flanagan, R.J.,
Detection and identification of volatile substances by headspace capillary gas chromatography to aid the diagnosis of acute poisoning,
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Ramsey and Flanagan, 1982
Ramsey, J.D.; Flanagan, R.J.,
Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse,
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. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Vibrational and/or electronic energy levels, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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