Dimethyl methylphosphonate

• Formula: C₃H₉O₃P
• Molecular weight: 124.0755
• IUPAC Standard InChI: InChI=1S/C3H9O3P/c1-5-7(3,4)6-2/h1-3H3 Copy

  
• IUPAC Standard InChIKey: VONWDASPFIQPDY-UHFFFAOYSA-N Copy
• CAS Registry Number: 756-79-6
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: DMMP; Dimethyl methanephosphonate; Phosphonic acid, methyl-, dimethyl ester; Methanephosphonic acid, dimethyl ester; Dimethoxymethylphosphine oxide; NCI-C54762; Pyrol DMMP; Methyl phosphonic acid, dimethyl ester; Dimethyl ester of methylphosphonic acid; Furan TF 2000; Fyrol DMMP; Metaran; O,O-Dimethyl methylphosphonate; NSC 62240; Phosphonic acid, P-methyl-, dimethyl ester
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Mass spectrum (electron ionization)
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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:
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

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

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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 compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (3.5 mL VAPORIZED AT 100 C); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution
• GAS (3.5 ml, VAPORIZED AT 100 C) $$ SEE SPECRUM NO. 10229 FOR "LIQUID" RUN; BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 2 cm^-1 resolution
• LIQUID (NEAT); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm^-1 resolution

Data compiled by: Tanya L. Myers, Russell G. Tonkyn, Ashley M. Oeck, Tyler O. Danby, John S. Loring, Matthew S. Taubman, Stephen W. Sharpe, Jerome C. Birnbaum, and Timothy J. Johnson

• liquid; Bruker Vertex 70 FTIR; 0.48217186 cm^-1 resolution

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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Kovats' RI, polar column, isothermal

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

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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, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes

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

Butrow, Buchanan, et al., 2009
Butrow, Ann B.; Buchanan, James H.; Tevault, David E., Vapor Pressure of Organophosphorus Nerve Agent Simulant Compounds, J. Chem. Eng. Data, 2009, 54, 6, 1876-1883, https://doi.org/10.1021/je8010024 . [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]

Frazer, Gerrard, et al., 1955
Frazer, M.J.; Gerrard, W.; Coulson, C.A.; Orgel, L.E.; Taylor, W.; Weiss, J.; Taylor, W.I.; Uyeo, S.; Yajima, H.; Kosolapoff, Gennady M.; McQuillin, F.J.; Stewart, J.; Henbest, H.B.; Owen, T.C.; Nayler, P.; Whiting, M.C.; Cadogan, J.I.G., Notes, J. Chem. Soc., 1955, 2959, https://doi.org/10.1039/jr9550002959 . [all data]

Kosolapoff, 1955
Kosolapoff, G.M., Vapour Pressures and Densities of Some Lower Alkylphosphonates, J. Chem. Soc., 1955, 2964-2965. [all data]

Zverev and Villem, 1980
Zverev, V.V.; Villem, Y.Y., Ionizationp potentials of phosphoryl compounds, J. Struct. Chem., 1980, 21, 22, In original 30. [all data]

Zverev, Villem, et al., 1979
Zverev, V.V.; Villem, Ya.Ya.; Bel'skii, V.E.; Kitaev, Yu.P., The photoelectronic spectra of phosphoryl compounds, Izv. Akad. Nauk SSSR, Ser. Khim., 1979, 1, 84. [all data]

Chattorpadhyay, Findley, et al., 1981
Chattorpadhyay, S.; Findley, G.L.; McGlynn, S.P., Photoelectron spectroscopy of phosphites and phosphates, J. Electron Spectrosc. Relat. Phenom., 1981, 24, 27. [all data]

Bafus, Gallegos, et al., 1966
Bafus, D.A.; Gallegos, E.J.; Kiser, R.W., An electron impact investigation of some alkyl phosphate esters, J. Phys. Chem., 1966, 70, 2614. [all data]

Huber, Kenndler, et al., 1993
Huber, J.F.K.; Kenndler, E.; Reich, G.; Hack, W.; Wolf, J., Optimal Selection of Gas Chromatographic Columns for the Analytical Control of Chemical Warfare Agents by Application of Information Theory to Retention Data, Anal. Chem., 1993, 65, 20, 2903-2906, https://doi.org/10.1021/ac00068a031 . [all data]

Kostiainen, 2000
Kostiainen, O., Gas Chromatography in Screening of Chemicals Related to the Chemical Weapons Convention in Encyclopedia of Analytical Chemistry, Meyers, R.A., ed(s)., John Wiley Sons Ltd, Chichester, 2000, 963-979. [all data]

Söderström, Ketola, et al., 1995
Söderström, M.T.; Ketola, R.A.; Kostiainen, O., Identification of some nerve agent homologues and dialkyl methylphosphonates by gas chromatography/Fourier transform infrared spectrometry. Part II. Spectral search with the help of retention indices, Fresenius J. Anal. Chem., 1995, 352, 6, 550-556, https://doi.org/10.1007/BF00323072 . [all data]

Staples, 2006
Staples, E.J., Creating a compound library for chemical warfare agents for the ZNose, 2006, retrieved from http://www.estcal.com/TechPapers/Security/CWA-Libraries.pdf. [all data]

Tsunoda, 2005
Tsunoda, N., The sarin incidents in Japan and mass spectrometry, J. MAss Spectrom. Soc. Japan, 2005, 53, 3, 157-163, https://doi.org/10.5702/massspec.53.157 . [all data]

OPCW, 1997
OPCW, Conference of the States Parties C-I/DEC.64 (22 May 1997), 1997, retrieved from http://www.opcw.org/html/global/c_series/csp1/CI_DEC64.html. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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