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Butane, 2-chloro-2-methyl-

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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
Deltafliquid-56.2 ± 0.4kcal/molCmArnett and Pienta, 1980Hydrochlorination
Quantity Value Units Method Reference Comment
Deltacliquid-795.3 ± 2.0kcal/molCcbSmith, Bjellerup, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -794. ± 2. kcal/mol

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
Tboil358.8KN/AWeast and Grasselli, 1989BS
Tboil358.KN/AKornblum, Smiley, et al., 1955Uncertainty assigned by TRC = 2. K; TRC
Tboil358.15KN/AKharasch and Buchi, 1951Uncertainty assigned by TRC = 2. K; TRC
Tboil358.75KN/AMumford and Phillips, 1950Uncertainty assigned by TRC = 0.5 K; TRC
Tboil358.8KN/ATimmermans, 1921Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tfus200.KN/AFleming and Whitmore, 1932Uncertainty assigned by TRC = 5. K; TRC
Tfus200.45KN/ATimmermans, 1921Uncertainty assigned by TRC = 0.5 K; TRC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
8.37295.AStephenson and Malanowski, 1987Based on data from 280. - 396. K. See also Dykyj, 1972.; AC
8.00 ± 0.20356.2VMathews and Fehlandt, 1931Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 7.34 kcal/mol; ALS

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Butane, 2-chloro-2-methyl- = Butane, 2-chloro-3-methyl-

By formula: C5H11Cl = C5H11Cl

Quantity Value Units Method Reference Comment
Deltar2.18kcal/molEqkEsipenok, Kabo, et al., 1973liquid phase; solvent: liquid phase
Deltar1.89 ± 0.05kcal/molEqkEsipenok, Kabo, et al., 1973liquid phase; solvent: cyclohexane

2-Butene, 2-methyl- + Hydrogen chloride = Butane, 2-chloro-2-methyl-

By formula: C5H10 + HCl = C5H11Cl

Quantity Value Units Method Reference Comment
Deltar-14.12 ± 0.22kcal/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochloroination

2-Methyl-1-butene + Hydrogen chloride = Butane, 2-chloro-2-methyl-

By formula: C5H10 + HCl = C5H11Cl

Quantity Value Units Method Reference Comment
Deltar-15.23 ± 0.34kcal/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochlorination

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)

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

H (mol/kg*bar) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.31 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.

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

Gas Phase Spectrum

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IR spectrum
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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Sadtler Research Labs Under US-EPA Contract
State gas

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


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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Mass spectrum
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Additional Data

View image of digitized spectrum (can be printed in landscape orientation).

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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-4936
NIST MS number 227753

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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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Column type Active phase Temperature (C) I Reference Comment
PackedSqualane27.638.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane49.642.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane67.645.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm
PackedSqualane86.650.Hively and Hinton, 1968He, Chromosorb P; Column length: 15. m; Column diameter: 0.25 mm

Kovats' RI, polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
PackedCarbowax 20M100.826.Castello and D'Amato, 1986He, Chromosorb W AW DMC; Column length: 3. m
PackedCarbowax 20M125.849.Castello and D'Amato, 1986He, Chromosorb W AW DMC; Column length: 3. m
PackedCarbowax 20M75.837.Castello and D'Amato, 1986He, Chromosorb W AW DMC; Column length: 3. m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
CapillaryPetrocol DH647.88White, Douglas, et al., 1992100. m/0.25 mm/0.5 «mu»m, He, 1. K/min; Tstart: 30. C; Tend: 220. C
CapillaryPetrocol DH647.89White, Douglas, et al., 1992100. m/0.25 mm/0.5 «mu»m, He, 1. K/min; Tstart: 30. C; Tend: 220. C
CapillaryPetrocol DH648.White, Hackett, et al., 1992100. m/0.25 mm/0.5 «mu»m, He, 1. K/min; Tstart: 30. C; Tend: 220. C
CapillarySE-54664.Weber, 198625. m/0.31 mm/0.17 «mu»m, H2, 2. K/min; Tstart: 35. C

Normal alkane RI, non-polar column, isothermal

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Column type Active phase Temperature (C) I Reference Comment
CapillaryApiezon L130.671.Arruda, Junkes, et al., 2008 
CapillarySqualane30.638.Tourres, 1968Nitrogen; Column length: 50. m; Column diameter: 0.25 mm
CapillarySqualane50.641.Tourres, 1968Nitrogen; Column length: 50. m; Column diameter: 0.25 mm

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

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Column type Active phase I Reference Comment
CapillaryMethyl Silicone657.Zenkevich, 1999Program: not specified
CapillaryPolydimethyl siloxanes657.Zenkevich and Chupalov, 1996Program: not specified

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law 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.

Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J., Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions, J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [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]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Kornblum, Smiley, et al., 1955
Kornblum, N.; Smiley, R.A.; Ungnade, H.E.; White, A.M.; Taub, B., The reaction of silver nitrite with secondary and tertiary alkyl halides, J. Am. Chem. Soc., 1955, 77, 5528-33. [all data]

Kharasch and Buchi, 1951
Kharasch, M.S.; Buchi, G., Reactions of Atoms and Free Radicals in Solution XXIV. The Reactions of Acetyl Peroxide with Chloro- and Dichloroalkanes, J. Am. Chem. Soc., 1951, 73, 632. [all data]

Mumford and Phillips, 1950
Mumford, S.A.; Phillips, J.W.C., 19. The Physical Properties of Some Aliphatic Compounds, J. Chem. Soc., 1950, 1950, 75-84. [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]

Fleming and Whitmore, 1932
Fleming, G.H.; Whitmore, F.C., Chlorination of Neopentane, J. Am. Chem. Soc., 1932, 54, 3460. [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, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [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]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Esipenok, Kabo, et al., 1973
Esipenok, G.E.; Kabo, G.Ya.; Andreevskii, D.N., Equilibrium and thermodynamics of the isomerisation of methylchlorobutanes, Russ. J. Phys. Chem. (Engl. Transl.), 1973, 47, 420. [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]

Castello and D'Amato, 1986
Castello, G.; D'Amato, G., Gas chromatographic separation and identification of linear and branched-chain alkyl chlorides, J. Chromatogr., 1986, 354, 65-74, https://doi.org/10.1016/S0021-9673(01)87011-4 . [all data]

White, Douglas, et al., 1992
White, C.M.; Douglas, L.J.; Hackett, J.P.; Anderson, R.R., Characterization of synthetic gasoline from the chloromethane-zeolite reaction, Energy Fuels, 1992, 6, 1, 76-82, https://doi.org/10.1021/ef00031a012 . [all data]

White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [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]

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]

Tourres, 1968
Tourres, D.A., Separation of mono- and dichloro-methyl butanes and of monochloro-methyl butenes by preparative gas chromatography, Chromatographia, 1968, 1, 11-12, 437-442, https://doi.org/10.1007/BF02255759 . [all data]

Zenkevich, 1999
Zenkevich, I.G., Mutual Correlation between Gas-Chromatographic Retention Indices of Organic Compounds from Different Series, Zh. Anal. Khim., 1999, 54, 12, 1272-1279. [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, NIST Free Links, References