Formamide, N,N-dimethyl-
- Formula: C3H7NO
- Molecular weight: 73.0938
- IUPAC Standard InChIKey: ZMXDDKWLCZADIW-UHFFFAOYSA-N
- CAS Registry Number: 68-12-2
- 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: Dimethylformamide; DMF; DMF (amide); DMFA; N-Formyldimethylamine; N,N-Dimethylformamide; HCON(CH3)2; Formyldimethylamine; Dimethylforamide; Dimethylformamid; Dimetilformamide; Dwumetyloformamid; N,N-Dimethylmethanamide; NSC-5356; U-4224; Dimethylamid kyseliny mravenci; Dimetylformamidu; NCI-C60913; UN 2265; DMF (dimethylformamide); N,N-Dimethylformaldehyde
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Condensed phase thermochemistry data
Go To: Top, Phase change 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -57.21 ± 0.29 | kcal/mol | Ccb | Vasil'eva, Zhil'tsova, et al., 1972 | ALS |
ΔfH°liquid | -57.13 | kcal/mol | Ccb | Medard and Thomas, 1957 | Heat of combustion corrected for pressure; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -464.06 ± 0.29 | kcal/mol | Ccb | Vasil'eva, Zhil'tsova, et al., 1972 | ALS |
ΔcH°liquid | -464.13 | kcal/mol | Ccb | Medard and Thomas, 1957 | Heat of combustion corrected for pressure; ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
34.907 | 298.15 | Grolier, Roux-Desgranges, et al., 1993 | DH |
35.411 | 298.15 | Kolker, Kulikov, et al., 1992 | T = 283 to 323 K.; DH |
35.679 | 308. | Kulikov, Krestov, et al., 1989 | DH |
35.85 | 298.15 | Petrov, Peshekhodov, et al., 1989 | T = 258.15, 278.15, 298.15, 318.15 K.; DH |
35.459 | 298.15 | Zegers and Somsen, 1984 | DH |
35.97 | 298.15 | Vorob'ev and Yakovlev, 1982 | T = 297.15 to 299.15 K. Cp given as 2.059 J/g*K.; DH |
36.04 | 298.15 | de Visser and Somsen, 1979 | DH |
28.80 | 298. | Marchidan and Ciopec, 1978 | T = 298 to 427 K. Mean value over range.; DH |
35.4 | 298.15 | De Visser, Perron, et al., 1977 | DH |
35.4 | 298. | De Visser, Perron, et al., 1977 | One temperature only.; DH |
36.04 | 298.15 | De Visser, Perron, et al., 1977, 2 | DH |
34.9 | 298.15 | Bonner and Cerutti, 1976 | DH |
36.33 | 298.15 | de Visser and Somsen, 1974 | DH |
37.450 | 298. | Geller, 1961 | T = 273 to 323 K.; DH |
Phase change data
Go To: Top, Condensed phase thermochemistry 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
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 426. ± 1. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 212.7 | K | N/A | Dreisbach, 1955 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 649.6 | K | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.6 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.82 | mol/l | N/A | Teja and Anselme, 1990 | Uncertainty assigned by TRC = 0.08 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 11.2 ± 0.1 | kcal/mol | CGC | Panneerselvam, Antony, et al., 2009 | Based on data from 463. to 513. K.; AC |
ΔvapH° | 11.2 | kcal/mol | A | Barone, Castronuovo, et al., 1985 | See also Majer and Svoboda, 1985.; AC |
ΔvapH° | 11.37 | kcal/mol | E | Geller, 1961, 2 | ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
10.3 | 361. | N/A | Muñoz, Montón, et al., 2005 | Based on data from 346. to 425. K.; AC |
9.99 | 392. | N/A | Blanco, Beltrán, et al., 1997 | Based on data from 377. to 426. K.; AC |
10.4 | 353. | N/A | Marzal, Gabaldon, et al., 1995 | Based on data from 338. to 425. K.; AC |
11.8 | 316. | A | Stephenson and Malanowski, 1987 | Based on data from 301. to 426. K.; AC |
10.2 | 370. | N/A | Bludilina, Baev, et al., 1979 | Based on data from 318. to 423. K.; AC |
13.6 | 346. | N/A | Myasinkova, Schmelev, et al., 1974 | Based on data from 331. to 425. K. See also Boublik, Fried, et al., 1984.; AC |
11.2 | 318. | N/A | Gopal and Rizvi, 1968 | Based on data from 303. to 363. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
303. to 363. | 3.92497 | 1337.716 | -82.648 | Gopal and Rizvi, 1968, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
2.139 | 212.85 | N/A | Karyakin, Rabinovich, et al., 1978 | DH |
2.14 | 212.9 | AC | Smirnova, Tsvetkova, et al., 2007 | AC |
2.14 | 212.9 | N/A | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.99 | 212.85 | Karyakin, Rabinovich, et al., 1978 | DH |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Vasil'eva, Zhil'tsova, et al., 1972
Vasil'eva, T.F.; Zhil'tsova, E.N.; Vvedenskii, A.A.,
Enthalpies of combustion of NN-dimethylformamide and NN-dimethylacetamide,
Russ. J. Phys. Chem. (Engl. Transl.), 1972, 46, 315. [all data]
Medard and Thomas, 1957
Medard, L.; Thomas, M.,
Chaleur de combustion de onze substances explosives ou apparentees a des explosifs,
Mem. Poudres, 1957, 39, 195-208. [all data]
Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E.,
Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide,
J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]
Kolker, Kulikov, et al., 1992
Kolker, A.M.; Kulikov, M.V.; Krestov, Al.G.,
Volumes and heat capacities of binary non-aqueous mixtures. Part 2. The systems acetonitrile-N,N-dimethylformamide and acetonitrile-hexamethylphosphoric triamide,
Thermochim. Acta, 1992, 211, 73-84. [all data]
Kulikov, Krestov, et al., 1989
Kulikov, M.V.; Krestov, A.G.; Safonova, L.P.; Kolker, A.M.,
Excess thermodynamic functions in the systems water + N-methylformamide, and water + N,N-dimethylformamide, Sbornik Nauch Trud., Termodin. rast. neelect., Ivanovo,
Inst. nevod. rast., 1989, Akad. [all data]
Petrov, Peshekhodov, et al., 1989
Petrov, A.N.; Peshekhodov, P.B.; Al'per, G.A.,
Heat capacity of non-aqueous solutions of non-electrolyts with N,N-dimethylformamide as a base, Sbornik Nauch. Trud., Termodin. Rast. neelect., Ivanovo,
Inst. nevod. rast., 1989, Akad. [all data]
Zegers and Somsen, 1984
Zegers, H.C.; Somsen, G.,
Partial molar volumes and heat capacities in (dimethylformamide + an n-alkanol),
J. Chem. Thermodynam., 1984, 16, 225-235. [all data]
Vorob'ev and Yakovlev, 1982
Vorob'ev, A.F.; Yakovlev, P.N.,
The specific heats of dimethylformamide-water and hexamethylphosphoramide-water mixtures,
Zhur. Fiz. Khim., 1982, 56, 1933-1936. [all data]
de Visser and Somsen, 1979
de Visser, C.; Somsen, G.,
Thermochemical behavior of mixtures of N,N-dimethylformamide with dimethylsulfoxide, acetonitrile, and N-methylformamide: volumes and heat capacities,
J. Solution Chem., 1979, 8, 593-600. [all data]
Marchidan and Ciopec, 1978
Marchidan, D.I.; Ciopec, M.,
Relative enthalpies and related thermodynamic functions of some organic compounds by drop calorimetry,
J. Therm. Anal., 1978, 14, 131-150. [all data]
De Visser, Perron, et al., 1977
De Visser, C.; Perron, G.; Desnoyers, J.E.,
Volumes and heat capacities of ternary aqueous systems at 25°C. Mixtures of urea, tert-butyl alcohol, N,N-dimethylformamide, and water,
J. Amer. Chem. Soc., 1977, 99, 5894-5900. [all data]
De Visser, Perron, et al., 1977, 2
De Visser, C.; Perron, G.; Desnoyers, J.E.; Heuvelsland, W.J.M.; Somsen, G.,
Volumes and heat capacities of mixtures of N,N-dimethylformamide and water at 298.15 K,
J. Chem. Eng. Data, 1977, 22, 74-79. [all data]
Bonner and Cerutti, 1976
Bonner, O.D.; Cerutti, P.J.,
The partial molar heat capacities of some solutes in water and deuterium oxide,
J. Chem. Thermodynam., 1976, 8, 105-111. [all data]
de Visser and Somsen, 1974
de Visser, C.; Somsen, G.,
Molar heat capacities of binary mixtures of water and some amides at 298.15 K,
Z. Physik. Chem. [N.F.], 1974, 92, 159-162. [all data]
Geller, 1961
Geller, B.E.,
Some physicochemical properties of dimethylformamide,
Zhur. Fiz. Khim., 1961, 35, 2210-2216. [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]
Teja and Anselme, 1990
Teja, A.S.; Anselme, M.J.,
The critical properties of thermally stable and unstable fluids. I. 1985 results,
AIChE Symp. Ser., 1990, 86, 279, 115-21. [all data]
Panneerselvam, Antony, et al., 2009
Panneerselvam, K.; Antony, M.P.; Srinivasan, T.G.; Vasudeva Rao, P.R.,
Enthalpies of vaporization of N,N-dialkyl monamides at 298.15K,
Thermochimica Acta, 2009, 495, 1-2, 1-4, https://doi.org/10.1016/j.tca.2009.05.007
. [all data]
Barone, Castronuovo, et al., 1985
Barone, G.; Castronuovo, G.; Della Gatta, G.; Elia, V.; Iannone, A.,
Enthalpies of vaporization of seven alkylamides,
Fluid Phase Equilibria, 1985, 21, 1-2, 157-164, https://doi.org/10.1016/0378-3812(85)90066-4
. [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]
Geller, 1961, 2
Geller, B.E.,
Properties of the dimethylformamide water system. I. Thermochemical properties,
Russ. J. Phys. Chem. (Engl. Transl.), 1961, 35, 542-564. [all data]
Muñoz, Montón, et al., 2005
Muñoz, R.; Montón, J.B.; Burguet, M.C.; de la Torre, J.,
Phase equilibria in the systems isobutyl alcohol+N,N-dimethylformamide, isobutyl acetate+N,N-dimethylformamide and isobutyl alcohol+isobutyl acetate+N,N-dimethylformamide at 101.3kPa,
Fluid Phase Equilibria, 2005, 232, 1-2, 62-69, https://doi.org/10.1016/j.fluid.2005.03.014
. [all data]
Blanco, Beltrán, et al., 1997
Blanco, Beatriz; Beltrán, Sagrario; Cabezas, José Luis; Coca, José,
Phase Equilibria of Binary Systems Formed by Hydrocarbons from Petroleum Fractions and the Solvents N -Methylpyrrolidone and N , N -Dimethylformamide. 1. Isobaric Vapor-Liquid Equilibria,
J. Chem. Eng. Data, 1997, 42, 5, 938-942, https://doi.org/10.1021/je970059u
. [all data]
Marzal, Gabaldon, et al., 1995
Marzal, Paula; Gabaldon, Carmen; Seco, Aurora; Monton, Juan B.,
Isobaric Vapor-Liquid Equilibria of 1-Butanol + N,N-Dimethylformamide and 1-Pentanol + N,N-Dimethylformamide Systems at 50.00 and 100.00 kPa,
J. Chem. Eng. Data, 1995, 40, 3, 589-592, https://doi.org/10.1021/je00019a010
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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]
Bludilina, Baev, et al., 1979
Bludilina, V.I.; Baev, A.K.; Matveev, V.K.; Gaidym, I.L.; Shcherbina, E.I.,
Zh. Fiz. Khim., 1979, 53, 1052. [all data]
Myasinkova, Schmelev, et al., 1974
Myasinkova, L.F.; Schmelev, V.A.; Vaisman, I.L.; Bushinskii, V.I.; Novokhatka, D.A.,
Zh. Prikl. Khim. (Leningrad), 1974, 47, 2604. [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]
Gopal and Rizvi, 1968
Gopal, R.; Rizvi, S.A.,
J. Indian Chem. Soc., 1968, 45, 1, 13. [all data]
Gopal and Rizvi, 1968, 2
Gopal, R.; Rizvi, S.A.,
Vapour Pressures of Some Mono- and Di-Alkyl Substituted Aliphatic Amides at Different Temperatures,
J. Indian Chem. Soc., 1968, 45, 1, 13-16. [all data]
Karyakin, Rabinovich, et al., 1978
Karyakin, N.V.; Rabinovich, I.B.; Pal'tseva, N.G.,
Thermodynamics of the reactions of aromatic diamines with dianhydrides of tetracarboxylic acids, Vysokomol. Soedin,
Ser., 1978, A 20(9), 2025-2029. [all data]
Smirnova, Tsvetkova, et al., 2007
Smirnova, N.N.; Tsvetkova, L.Ya.; Bykova, T.A.; Marcus, Yizhak,
Thermodynamic properties of N,N-dimethylformamide and N,N-dimethylacetamide,
The Journal of Chemical Thermodynamics, 2007, 39, 11, 1508-1513, https://doi.org/10.1016/j.jct.2007.02.009
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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
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Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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