Dimethyl phosphite
- Formula: C2H7O3P
- Molecular weight: 110.0489
- IUPAC Standard InChIKey: HZCDANOFLILNSA-UHFFFAOYSA-N
- CAS Registry Number: 868-85-9
- 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. - Species with the same structure:
- Isotopologues:
- Other names: Phosphonic acid, dimethyl ester; Dimethoxyphosphine oxide; Dimethyl acid phosphite; Dimethyl hydrogen phosphite; Dimethyl phosphonate; Hydrogen dimethyl phosphite; Methyl phosphonate ((MeO)2HPO); O,O-Dimethyl phosphonate; (CH3O)2PHO; Phosphorous acid dimethyl ester; Dimethylester kyseliny fosforite; Dimethylfosfit; Dimethylfosfonat; NCI-C54773; Dimethyl ester of phosphonic acid; Dimethyl hydrogen phosphonate
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Phase change data
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data compiled by: William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔvapH° | 11.2 | kcal/mol | GS | Butrow, Buchanan, et al., 2009 | Based on data from 243. to 443. K. |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
11.2 | 368. | N/A | Fan and Wang, 2010 | Based on data from 353. to 443. K. |
11.5 | 243. | GS | Butrow, Buchanan, et al., 2009 | Based on data from 243. to 443. K. |
11.4 | 263. | GS | Butrow, Buchanan, et al., 2009 | Based on data from 243. to 443. K. |
11.1 | 313. | GS | Butrow, Buchanan, et al., 2009 | Based on data from 243. to 443. K. |
11.0 | 333. | GS | Butrow, Buchanan, et al., 2009 | Based on data from 243. to 443. K. |
10.9 | 373. | GS | Butrow, Buchanan, et al., 2009 | Based on data from 243. to 443. K. |
9.25 | 361. | A | Stephenson and Malanowski, 1987 | Based on data from 346. to 456. K. See also Dykyj, 1970. |
Gas phase ion energetics data
Go To: Top, Phase change data, Mass spectrum (electron ionization), 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
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 C2H7O3P+ (ion structure unspecified)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Proton affinity (review) | 213.9 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 206.1 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.53 | PE | Zverev and Villem, 1980 | LLK |
10.53 | PE | Zverev, Villem, et al., 1979 | LLK |
10.5 | EI | Fischler and Halmann, 1964 | RDSH |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
CH4O3P+ | 11.9 | ? | EI | Fischler and Halmann, 1964 | RDSH |
C2H6O3P+ | 12.7 | H | EI | Fischler and Halmann, 1964 | RDSH |
PHO3+ | 11.2 | ? | EI | Fischler and Halmann, 1964 | RDSH |
PO+ | 16.3 | ? | EI | Fischler and Halmann, 1964 | RDSH |
PO3+ | 13.5 | ? | EI | Fischler and Halmann, 1964 | RDSH |
De-protonation reactions
C2H6O3P- + =
By formula: C2H6O3P- + H+ = C2H7O3P
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 356.5 ± 3.6 | kcal/mol | G+TS | McDonald, Chowdhury, et al., 1987 | gas phase; Acidity between MeNO2, EtSH. Acid taken as (MeO)2P(O)H.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 349.3 ± 3.5 | kcal/mol | IMRB | McDonald, Chowdhury, et al., 1987 | gas phase; Acidity between MeNO2, EtSH. Acid taken as (MeO)2P(O)H.; B |
ΔrG° | 351.0 ± 4.0 | kcal/mol | IMRB | Anderson, DePuy, et al., 1984 | gas phase; Between MeSH, H2S; B |
Mass spectrum (electron ionization)
Go To: Top, Phase change data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
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- 989 |
NIST MS number | 230474 |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]
Fan and Wang, 2010
Fan, Chuan-Lei; Wang, Li-Sheng,
Vapor Pressure of Dimethyl Phosphite and Dimethyl Methylphosphonate,
J. Chem. Eng. Data, 2010, 55, 1, 479-481, https://doi.org/10.1021/je900258f
. [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, 1970
Dykyj, J.,
Petrochemica, 1970, 10, 2, 51. [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]
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]
Fischler and Halmann, 1964
Fischler, J.; Halmann, M.,
Electron-impact studies of phosphorus compounds,
J. Chem. Soc., 1964, 31. [all data]
McDonald, Chowdhury, et al., 1987
McDonald, R.M.; Chowdhury, A.K.; Gung, W.Y.; DeWitt, K.D.,
Nucleophilic Reactivity in Anionic Ion-Molecule Reactions
in Nucleophilicity, Harris, J.M, McManus, S.P. Eds., Amer. Chem. Soc, 1987. [all data]
Anderson, DePuy, et al., 1984
Anderson, D.R.; DePuy, C.H.; Filley, J.; Bierbaum, V.M.,
Gas Phase Chemistry of Trimethyl Phosphite,
J. Am. Chem. Soc., 1984, 106, 22, 6513, https://doi.org/10.1021/ja00334a009
. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions 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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