Chloromethane

• Formula: CH₃Cl
• Molecular weight: 50.488
• IUPAC Standard InChI: InChI=1S/CH3Cl/c1-2/h1H3 Copy

  
• IUPAC Standard InChIKey: NEHMKBQYUWJMIP-UHFFFAOYSA-N Copy
• CAS Registry Number: 74-87-3
• 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: Methane, chloro-; Methyl chloride; Artic; Freon 40; Monochloromethane; CH3Cl; Chloor-methaan; Chlor-methan; Chlorure de methyle; Clorometano; Cloruro di metile; Methylchlorid; Metylu chlorek; R 40; Rcra waste number U045; UN 1063; Refrigerant R40
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Phase change data

Go To: Top, 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Entropy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Gas phase ion energetics data

Go To: Top, Phase change data, 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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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 CH₃Cl⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

CH₂Cl^- +  =

By formula: CH₂Cl^- + H⁺ = CH₃Cl

References

Go To: Top, Phase change data, Gas phase ion energetics data, Notes

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

Awbery, 1941
Awbery, J.H., Philos. Mag., 1941, 31, 247. [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]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]

Messerly and Aston, 1940
Messerly, G.H.; Aston, J.G., The Heat Capacity and Entropy, Heats of Fusion and Vaporization and the Vapor Pressure of Methyl Chloride, J. Am. Chem. Soc., 1940, 62, 886-90. [all data]

Mansoorian, Hall, et al., 1981
Mansoorian, H.; Hall, K.R.; Holste, J.C.; Eubank, P.T., The density of gaseous ethane and of fluid methyl chloride and the vapor pressure of methyl chloride, J. Chem. Thermodyn., 1981, 13, 1001-24. [all data]

Hsu and McKetta, 1964
Hsu, C.C.; McKetta, J.J., Pressure-Volume-Temperature Properties of Methyl Chloride, J. Chem. Eng. Data, 1964, 9, 1, 45-51, https://doi.org/10.1021/je60020a014 . [all data]

Leduc, 1909
Leduc, A., Compressibility of gases between 0 atm and 3 atm and at all temperatures, C. R. Hebd. Seances Acad. Sci., 1909, 148, 407. [all data]

Vincent and Chappuis, 1886
Vincent, C.; Chappuis, J., J. Phys. Theor. Appl., 1886, 5, 58. [all data]

Centnerszwer, 1904
Centnerszwer, M., An Application of the Method of Cailletet and Mathias to Determine Critical Volume., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1904, 49, 199. [all data]

Manion, 2002
Manion, J.A., Evaluated Enthalpies of Formation of the Stable Closed Shell C1 and C2 Chlorinated Hydrocarbons, J. Phys. Chem. Ref. Data, 2002, 31, 1, 123-172, https://doi.org/10.1063/1.1420703 . [all data]

Messerly and Aston, 1940, 2
Messerly, G.H.; Aston, J.G., The heat capacity and entropy, heats of fusion and vaporization and the vapor pressure of methyl chloride, J. Am. Chem. Soc., 1940, 62, 886-890. [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]

Ganeff and Jungers, 2010
Ganeff, Jean M.; Jungers, Joseph C., Tensions de vapeur du système CH3Cl «63743» CH2Cl2, Bull. Soc. Chim. Belges, 2010, 57, 1-3, 82-87, https://doi.org/10.1002/bscb.19480570109 . [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]

Thomson, 1946
Thomson, George Wm., The Antoine Equation for Vapor-pressure Data., Chem. Rev., 1946, 38, 1, 1-39, https://doi.org/10.1021/cr60119a001 . [all data]

Yates, 1926
Yates, G.W.C., LXXIV. Latent heats of vaporization of ethyl and methyl chlorides, Philos. Mag., 1926, 2, 817-826. [all data]

Ganeff and Jungers, 1948
Ganeff, J.M.; Jungers, J.C., Tensions de Vapeur du Systeme CH3Cl - CH2Cl2, Bull. Soc. Chim. Belg., 1948, 57, 1-3, 82-87, https://doi.org/10.1002/bscb.19480570109 . [all data]

Beersmans and Jungers, 1947
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]

Bah and Dupont-Pavlovsky, 1995
Bah, A.; Dupont-Pavlovsky, N., Vapor Pressure of Solid Chloromethane, J. Chem. Eng. Data, 1995, 40, 4, 869-870, https://doi.org/10.1021/je00020a028 . [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]

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]

Hochmann, Templet, et al., 1975
Hochmann, P.; Templet, P.H.; Wang, H.-t.; McGlynn, S.P., Molecular Rydberg transitions. I. Low-energy Rydberg transitions in methyl halides, J. Chem. Phys., 1975, 62, 2588. [all data]

Werner, Tsai, et al., 1974
Werner, A.S.; Tsai, B.P.; Baer, T., Photoionization study of the ionization potentials fragmentation paths of the chlorinated methanes carbon tetrabromide, J. Chem. Phys., 1974, 60, 3650. [all data]

Lossing, 1972
Lossing, F.P., Free radicals by mass spectrometry. XLIV. Ionization potentials bond dissociation energies for chloro-and fluoromethyl radicals, Bull. Soc. Chim. Belg., 1972, 81, 125. [all data]

Ragle, Stenhouse, et al., 1970
Ragle, J.L.; Stenhouse, I.A.; Frost, D.C.; McDowell, C.A., Valence-shell ionization potentials of halomethanes by photoelectron spectroscopy. I. CH₃Cl, CH₃Br, CH₃I. Vibrational frequencies and vibronic interaction in CH₃Br⁺ and CH₃Cl⁺, J. Chem. Phys., 1970, 53, 178. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Nicholson, 1965
Nicholson, A.J.C., Photoionization-efficiency curves. II. False and genuine structure, J. Chem. Phys., 1965, 43, 1171. [all data]

Dibeler and Walker, 1965
Dibeler, V.H.; Walker, J.A., Ion-pair process in CH₃Cl by photoionization, J. Chem. Phys., 1965, 43, 1842. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Price, 1936
Price, W.C., The far ultraviolet absorption spectra and ionization potentials of the alkyl halides. Part I, J. Chem. Phys., 1936, 4, 539. [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]

Utsunomiya, Kobayashi, et al., 1980
Utsunomiya, C.; Kobayashi, T.; Nagakura, S., Photoelectron angular distribution measurements for some aliphatic alcohols, amines, halides, Bull. Chem. Soc. Jpn., 1980, 53, 1216. [all data]

Uehara, Saito, et al., 1973
Uehara, Y.; Saito, N.; Yonezawa, T., Ionization potentials of trifluoromethyl and methyl halides by photoelectron spectroscopy and calculations by extended Hucket and CNDO/2 methods, Chem. Lett., 1973, 495. [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]

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]

Tsuda and Hamill, 1964
Tsuda, S.; Hamill, W.H., Structure in ionization efficiency curves near threshold from alkanes and alkyl halides, J. Chem. Phys., 1964, 41, 2713. [all data]

Martin, Lampe, et al., 1966
Martin, R.H.; Lampe, F.W.; Taft, R.W., An electron-impact study of ionization and dissociation in methoxy- and halogen- substituted methanes, J. Am. Chem. Soc., 1966, 88, 1353. [all data]

Krauss, Walker, et al., 1968
Krauss, M.; Walker, J.A.; Dibeler, V.H., Mass spectrometric study of photoionization. X. Hydrogen chloride and methyl halides, J. Res. NBS, 1968, 72A, 281. [all data]

Tsuda, Melton, et al., 1964
Tsuda, S.; Melton, C.E.; Hamill, W.H., Ionization- efficiency curves for molecular and fragment ions from methane and the methyl halides, J. Chem. Phys., 1964, 41, 689. [all data]

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 acidity of CH₃X [X = P(CH₃)₂, SCH₃, F, Cl, Br, I] compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 837. [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]

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Henchman, Hierl, et al., 1985
Henchman, M.; Hierl, P.M.; Paulson, J.F., Nucleophilic displacement vs. proton tranfer: The system OH-.(H₂O)_0,1,2 + CH₃Cl in the relative energy range 0.03-5 eV, J. Am. Chem. Soc., 1985, 107, 2812. [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  Ptriple	Triple point pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization
  ρc	Critical density

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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