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
• 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
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Gas Phase Heat Capacity (Shomate Equation)

C_p° = A + B*t + C*t² + D*t³ + E/t²
H° − H°_298.15= A*t + B*t²/2 + C*t³/3 + D*t⁴/4 − E/t + F − H
S° = A*ln(t) + B*t + C*t²/2 + D*t³/3 − E/(2*t²) + G
    C_p = heat capacity (J/mol*K)
    H° = standard enthalpy (kJ/mol)
    S° = standard entropy (J/mol*K)
    t = temperature (K) / 1000.

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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Henry's Law 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 (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

 +  = ( • )

By formula: Cl^- + CH₃Cl = (Cl^- • CH₃Cl)

CH₂Cl^- +  =

By formula: CH₂Cl^- + H⁺ = CH₃Cl

(CH₂Cl⁺ • ) +  = (CH₂Cl⁺ • 2)

By formula: (CH₂Cl⁺ • CH₃Cl) + CH₃Cl = (CH₂Cl⁺ • 2CH₃Cl)

Free energy of reaction

(CH₄Cl⁺ • ) +  = (CH₄Cl⁺ • 2)

By formula: (CH₄Cl⁺ • CH₃Cl) + CH₃Cl = (CH₄Cl⁺ • 2CH₃Cl)

Free energy of reaction

CH₂Cl⁺ +  = (CH₂Cl⁺ • )

By formula: CH₂Cl⁺ + CH₃Cl = (CH₂Cl⁺ • CH₃Cl)

Free energy of reaction

C₃H₇⁺ +  = (C₃H₇⁺ • )

By formula: C₃H₇⁺ + CH₃Cl = (C₃H₇⁺ • CH₃Cl)

 +  = ( • )

By formula: CH₃⁺ + CH₃Cl = (CH₃⁺ • CH₃Cl)

 +  = ( • )

By formula: Br^- + CH₃Cl = (Br^- • CH₃Cl)

CN^- +  = (CN^- • )

By formula: CN^- + CH₃Cl = (CN^- • CH₃Cl)

CH₃Cl₂^- + 2 = C₂H₆Cl₃^-

By formula: CH₃Cl₂^- + 2CH₃Cl = C₂H₆Cl₃^-

C₂H₆Cl₃^- + 3 = C₃H₉Cl₄^-

By formula: C₂H₆Cl₃^- + 3CH₃Cl = C₃H₉Cl₄^-

C₃H₉Cl₄^- + 4 = C₄H₁₂Cl₅^-

By formula: C₃H₉Cl₄^- + 4CH₃Cl = C₄H₁₂Cl₅^-

C₄H₁₂Cl₅^- + 5 = C₅H₁₅Cl₆^-

By formula: C₄H₁₂Cl₅^- + 5CH₃Cl = C₅H₁₅Cl₆^-

C₅H₁₅Cl₆^- + 6 = C₆H₁₈Cl₇^-

By formula: C₅H₁₅Cl₆^- + 6CH₃Cl = C₆H₁₈Cl₇^-

C₆H₁₈Cl₇^- + 7 = C₇H₂₁Cl₈^-

By formula: C₆H₁₈Cl₇^- + 7CH₃Cl = C₇H₂₁Cl₈^-

C₇H₂₁Cl₈^- + 8 = C₈H₂₄Cl₉^-

By formula: C₇H₂₁Cl₈^- + 8CH₃Cl = C₈H₂₄Cl₉^-

C₂H₅⁺ +  = (C₂H₅⁺ • )

By formula: C₂H₅⁺ + CH₃Cl = (C₂H₅⁺ • CH₃Cl)

 +  = ( • )

By formula: Li⁺ + CH₃Cl = (Li⁺ • CH₃Cl)

C₄H₉⁺ +  = (C₄H₉⁺ • )

By formula: C₄H₉⁺ + CH₃Cl = (C₄H₉⁺ • CH₃Cl)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + CH₃Cl = (CH₆N⁺ • CH₃Cl)

 +  =  + 

By formula: H₂ + CH₃Cl = CH₄ + HCl

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)

References

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

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

Chase, 1998
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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]

Fletcher and Pilcher, 1971
Fletcher, R.A.; Pilcher, G., Measurements of heats of combustion by flame calorimetry. Part 7.?Chloromethane, chloroethane, 1-chloropropane, 2-chloropropane, Trans. Faraday Soc., 1971, 67, 3191, https://doi.org/10.1039/tf9716703191 . [all data]

Fletcher and Pilcher, 1971, 2
Fletcher, R.A.; Pilcher, G., Measurements of heats of combustion by flame calorimetry. Part 7.-Chloromethane, chloroethane, 1-chloropropane, 2-chloropropane, Trans. Faraday Soc., 1971, 67, 3191-3201. [all data]

Lacher, Emery, et al., 1956
Lacher, J.R.; Emery, E.; Bohmfalk, E.; Park, J.D., Reaction heats of organic compounds. IV. A high temperature calorimeter and the hydrogenation of methyl ethyl and vinyl chlorides, J. Phys. Chem., 1956, 60, 492-495. [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]

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, 886-890. [all data]

Awberg and Griffiths, 1940
Awberg, J.H.; Griffiths, E., The specific heat of liquid methyl chloride, Proc. Phys. Soc. (London), 1940, 52, 770-776. [all data]

Shorthose, 1924
Shorthose, D.N., G. B. DSIR, Food Invest. Board, Spec. Rept., 1924, No. 19, 16pp. [all data]

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, 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, 886-90. [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]

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]

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]

Hiraoka, Mizuno, et al., 2001
Hiraoka, K.; Mizuno, T.; Iino, T.; Eguchi, D.; Yamabe, S., Characteristic changes of bond energies for gas-phase cluster ions of halide ions with methane and chloromethanes, J. Phys. Chem. A, 2001, 105, 20, 4887-4893, https://doi.org/10.1021/jp010143n . [all data]

Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

Dougherty, Dalton, et al., 1974
Dougherty, R.C.; Dalton, J.; Roberts, J.D., SN₂ reactions in the gas phase: Structure of the transition state, Org. Mass Spectrom., 1974, 8, 77. [all data]

Yamdagni and Kebarle, 1971
Yamdagni, R.; Kebarle, P., Hydrogen bonding energies to negative ions from gas phase measurements of ionic equilibria, J. Am. Chem. Soc., 1971, 93, 7139. [all data]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [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]

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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
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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]

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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]

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Luczynski, Z.; Malicki, W.; Wincel, H., Positive Ion Reactions of Methyl Cloride in the Gas Phase, Int. J. Mass Spectrom. Ion Phys., 1974, 15, 3, 321, https://doi.org/10.1016/0020-7381(74)85009-6 . [all data]

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Sen Sharma, D.K.; Kebarle, P., Binding Energies and Stabilities of Chloronium Ions from Study of the Gas - Phase Equilibria: R1+ + ClR2 = R1ClR2+, J. Am. Chem. Soc., 1978, 100, 18, 5826, https://doi.org/10.1021/ja00486a039 . [all data]

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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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Notes

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

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  Ptriple	Triple point pressure
  S°gas,1 bar	Entropy of gas at standard conditions (1 bar)
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) 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
  ΔcH°gas	Enthalpy of combustion of gas 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
  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
  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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