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
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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 (atm)
    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

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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Additional Data

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

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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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