Acetic acid, chloro-, methyl ester
- Formula: C3H5ClO2
- Molecular weight: 108.524
- IUPAC Standard InChIKey: QABLOFMHHSOFRJ-UHFFFAOYSA-N
- CAS Registry Number: 96-34-4
- 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: Methyl chloroacetate; Methyl monochloroacetate; Monochloroacetic acid, methyl ester; ClH2CCOOCH3; Chloroacetic acid methyl ester; Methyl chloroethanoate; Methyl monochloracetate; Methylester kyseliny chloroctove; UN 2295; Methyl ester of chloroacetic acid; Acetic acid, 2-chloro-, methyl ester; NSC 2635
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -444. ± 10. | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -487.0 ± 8.8 | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -1451. | kJ/mol | Ccb | Schjanberg, 1935 |
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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 403. ± 3. | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 241.0 | K | N/A | Dreisbach, 1955 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 240.50 | K | N/A | Timmermans, 1922 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 46.74 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 43.4 ± 4.2 | kJ/mol | E | Guthrie and Cullimore, 1980 | Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol; ALS |
ΔvapH° | 46.73 ± 0.06 | kJ/mol | C | Laynez and Wadso, 1972 | ALS |
ΔvapH° | 46.7 ± 0.1 | kJ/mol | C | Laynez, Wadsö, et al., 1972 | AC |
Reduced pressure boiling point
Tboil (K) | Pressure (bar) | Reference | Comment |
---|---|---|---|
403.2 | 0.987 | Aldrich Chemical Company Inc., 1990 | BS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
39.23 | 402.6 | N/A | Majer and Svoboda, 1985 | |
45.5 | 333. | A | Stephenson and Malanowski, 1987 | Based on data from 318. to 402. K. See also Goebel, Schaffenger, et al., 1967 and Boublik, Fried, et al., 1984.; AC |
46.7 | 313. | N/A | Nelson, 1928 | Based on data from 298. to 403. K. See also Boublik, Fried, et al., 1984.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
318.17 to 403.01 | 4.28118 | 1390.083 | -77.51 | Goevel, Schaffenger, et al., 1967 | Coefficents calculated by NIST from author's data. |
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 by: 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: C5H11ClO3 + H2O = 2CH4O + C3H5ClO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -32.6 ± 1.1 | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase; Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol |
By formula: H2O + C3H5ClO2 = CH4O + C2H3ClO2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -57.3 ± 2.9 | kJ/mol | Eqk | Guthrie and Cullimore, 1980 | liquid phase; Using Hf(s,ClCH2COOH)=-122.0±2.0 kcal/mol |
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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.3 | PE | Cannington and Ham, 1985 | LBLHLM |
10.53 ± 0.05 | EI | Pignataro, Foffani, et al., 1966 | RDSH |
10.7 | PE | Cannington and Ham, 1985 | Vertical value; LBLHLM |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C2H3O2+ | 11.10 ± 0.05 | CH2Cl | EI | Blanchette, Holmes, et al., 1986 | LBLHLM |
C2H3O2+ | 11.50 ± 0.05 | ? | EI | Briggs and Shannon, 1969 | RDSH |
C2H5Cl+ | 10.7 ± 0.2 | CO2 | EI | Blanchette, Holmes, et al., 1987 | LBLHLM |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)
- SOLUTION (10% IN CCl4 FOR 3800-1300, 10% IN CS2 FOR 1300-650, 10% IN CCl4 FOR 650-230 CM-1) VERSUS SOLVENT; PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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
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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-2175 |
NIST MS number | 228208 |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 100. | 708. | Haken and Korhonen, 1986 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 120. | 691. | Haken and Korhonen, 1986 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 140. | 679. | Haken and Korhonen, 1986 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Capillary | SE-30 | 80. | 705. | Haken and Korhonen, 1986 | N2; Column length: 25. m; Column diameter: 0.33 mm |
Capillary | OV-101 | 80. | 729.4 | Komárek, Hornová, et al., 1982 | N2; Column length: 15. m; Column diameter: 0.22 mm |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | OV-351 | 100. | 1270. | Haken and Korhonen, 1986 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Capillary | OV-351 | 140. | 1314. | Haken and Korhonen, 1986 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Capillary | OV-351 | 160. | 1345. | Haken and Korhonen, 1986 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Capillary | OV-351 | 180. | 1318. | Haken and Korhonen, 1986 | N2; Column length: 25. m; Column diameter: 0.32 mm |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP-1 | 731. | Peters, de Leer, et al., 1994 | 25. m/0.2 mm/0.33 μm, He, 50. C @ 5. min, 8. K/min, 300. C @ 10. min |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Guthrie and Cullimore, 1980
Guthrie, J.P.; Cullimore, P.A.,
Effect of the acyl substituent on the equilibrium constant for hydration of esters,
Can. J. Chem., 1980, 58, 1281-1294. [all data]
Schjanberg, 1935
Schjanberg, E.,
Die Verbrennungswarmen und die Refraktionsdaten einiger chlorsubstituierter Fettsauren und Ester.,
Z. Phys. Chem. Abt. A, 1935, 172, 197-233. [all data]
Dreisbach, 1955
Dreisbach, R.R.,
Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]
Timmermans, 1922
Timmermans, J.,
Investigation of the Freezing Point of Organic Substances VII,
Bull. Soc. Chim. Belg., 1922, 31, 389. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Laynez and Wadso, 1972
Laynez, J.; Wadso, I.,
Enthalpies of vaporization of organic compounds. IX. Some halogen substituted hydrocarbons and esters,
Acta Chem. Scand., 1972, 26, 3148. [all data]
Laynez, Wadsö, et al., 1972
Laynez, José; Wadsö, Ingemar; Haug, Arne; Songstad, J.; Pilotti, Åke,
Enthalpies of Vaporization of Organic Compounds. IX. Some Halogen Substituted Hydrocarbons and Esters.,
Acta Chem. Scand., 1972, 26, 3148-3152, https://doi.org/10.3891/acta.chem.scand.26-3148
. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Goebel, Schaffenger, et al., 1967
Goebel, K.H.; Schaffenger, J.; Opel, G.,
Chem. Tech. (Leipzig), 1967, 19, 307. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Nelson, 1928
Nelson, O.A.,
Vapor Pressures of Fumigants: I---Methyl, Ethyl, Isopropyl, and Secondary Butyl Chloroacetates 1,
Ind. Eng. Chem., 1928, 20, 12, 1380-1382, https://doi.org/10.1021/ie50228a034
. [all data]
Goevel, Schaffenger, et al., 1967
Goevel, K.-H.; Schaffenger, J.; Opel, G.,
Die Viskositat des Dampfes von Chloressigsauremthylester zwischen 80 und 150 °C und sein Sattigungsdruck 77 und 130 °C,
Chem. Tech. (Leipzig), 1967, 19, 5, 307-308. [all data]
Cannington and Ham, 1985
Cannington, P.H.; Ham, N.S.,
He(II) photoelectron spectra of esters,
J. Electron Spectrosc. Relat. Phenom., 1985, 36, 203. [all data]
Pignataro, Foffani, et al., 1966
Pignataro, S.; Foffani, A.; Innorta, G.; Distefano, G.,
Molecular structural effects on the ionization potentials for metasubstituted aromatic compounds and for compounds of the type X-CH2-R,
Z. Physik. Chem. (Frankfurt), 1966, 49, 291. [all data]
Blanchette, Holmes, et al., 1986
Blanchette, M.C.; Holmes, J.L.; Hop, C.E.C.A.; Lossing, F.P.; Postma, R.; Ruttink, P.J.A.; Terlouw, J.K.,
Theory and experiment in concert; the CH3O-C=O+ ion and its isomers,
J. Am. Chem. Soc., 1986, 108, 7589. [all data]
Briggs and Shannon, 1969
Briggs, P.R.; Shannon, T.W.,
The heat of formation of the methoxycarbonyl ion,
J. Am. Chem. Soc., 1969, 91, 4307. [all data]
Blanchette, Holmes, et al., 1987
Blanchette, M.C.; Holmes, J.L.; Lossing, F.P.,
The ethyl halides: Stable neutral and radical cation isomers [C2, H5, X] where X = F, Cl, Br, I,
Org. Mass Spectrom., 1987, 22, 701. [all data]
Haken and Korhonen, 1986
Haken, J.R.; Korhonen, I.O.O.,
Gas chromatography of homologous esters. XXXIII. Capillary chromatography of monochlorinated C1-C8 n-alkyl acetates, chloracetates, dichloroacetates and trichloroacetates,
J. Chromatogr., 1986, 357, 253-271, https://doi.org/10.1016/S0021-9673(01)95828-5
. [all data]
Komárek, Hornová, et al., 1982
Komárek, K.; Hornová, L.; Churácek, J.,
Glass capillary gas chromatography of homologous series of esters. Separation of homologous series of esters of halogenated carboxylic acids on a glass capillary column with the non-polar stationary silicone phase OV-101,
J. Chromatogr., 1982, 244, 1, 142-147, https://doi.org/10.1016/S0021-9673(00)80131-4
. [all data]
Peters, de Leer, et al., 1994
Peters, R.J.D.; de Leer, E.W.B.; Versteegh, J.F.M.,
Identification of Halogenated Compounds Produced by Chlorination of Humic Acid in the Presence of Bromide,
J. Chromatogr. A, 1994, 686, 2, 253-261, https://doi.org/10.1016/0021-9673(94)00719-5
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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