Coumarin
- Formula: C9H6O2
- Molecular weight: 146.1427
- IUPAC Standard InChIKey: ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
- CAS Registry Number: 91-64-5
- 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. - Isotopologues:
- Other names: 2H-1-Benzopyran-2-one; cis-o-Coumarinic acid lactone; o-Hydroxycinnamic acid lactone; Benzo-α-pyrone; Coumarinic anhydride; Rattex; Tonka bean camphor; 1,2-Benzopyrone; 2-Propenoic acid, 3-(2-hydroxyphenyl)-, δ-lactone; 2H-Benzo[b]pyran-2-one; o-Hydroxycinnamic lactone; Cinnamic acid, o-hydroxy-, δ-lactone; Cumarin; 2-Oxo-1,2-benzopyran; 2H-1-Benzopyran, 2-oxo-; o-Hydroxyzimtsaure-lacton; Kumarin; NCI C07103; NSC 8774; 2H-Chromen-2-one
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Phase change data
Go To: Top, 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 571.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 564. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 343. | K | N/A | Buckingham and Donaghy, 1982 | BS |
Tfus | 343.05 | K | N/A | Serpinskii, Voitkevich, et al., 1958 | Uncertainty assigned by TRC = 1.5 K; TRC |
Tfus | 340. | K | N/A | Sorum and Durand, 1952 | Uncertainty assigned by TRC = 1.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔsubH° | 95.4 ± 2.6 | kJ/mol | C | Matos, Sousa, et al., 2009 | AC |
ΔsubH° | 83.1 | kJ/mol | C | El Watik and Sabbah, 1991 | See also Sabbah and Watik, 1992.; AC |
ΔsubH° | 83.09 ± 0.22 | kJ/mol | C | Watik and Sabbah, 1991 | ALS |
ΔsubH° | 83.1 | kJ/mol | N/A | Watik and Sabbah, 1991 | DRB |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
63.2 | 394. | A | Stephenson and Malanowski, 1987 | Based on data from 379. to 463. K. See also Stull, 1947.; 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 |
---|---|---|---|---|---|
379. to 564. | 5.31529 | 2797.239 | -37.541 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
83.090 | 298.15 | N/A | Sabbah and El Watik, 1992 | DH |
86.2 | 323. | ME | Serpinskii, Voitkevich, et al., 1953 | Based on data from 293. to 353. K. See also Jones, 1960 and Stephenson and Malanowski, 1987.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.140 | 342.14 | N/A | Sabbah and El Watik, 1992 | DH |
19.140 | 342.14 | N/A | El Watik and Sabbah, 1991, 2 | DH |
18.63 | 342.3 | DSC | Matos, Sousa, et al., 2009 | AC |
19.14 | 342.1 | N/A | Domalski and Hearing, 1996 | AC |
References
Go To: Top, Phase change data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Serpinskii, Voitkevich, et al., 1958
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Yu.,
Trudy Vsesoyuz. Nauch.-Issledovatel. Inst. Sintet. I. Natural. Dushistykh Veshchestv, 1958, 4, 125. [all data]
Sorum and Durand, 1952
Sorum, C.H.; Durand, E.A.,
The Melting of Binary Eutectics,
J. Am. Chem. Soc., 1952, 74, 1071. [all data]
Matos, Sousa, et al., 2009
Matos, M. Agostinha R.; Sousa, Clara C.S.; Miranda, Margarida S.; Morais, Victor M.F.; Liebman, Joel F.,
Energetics of Coumarin and Chromone,
J. Phys. Chem. B, 2009, 113, 32, 11216-11221, https://doi.org/10.1021/jp9026942
. [all data]
El Watik and Sabbah, 1991
El Watik, L.; Sabbah, R.,
Thermodynamic study of coumarin and anthrone,
Bull. Soc. Chim. Fr., 1991, 344. [all data]
Sabbah and Watik, 1992
Sabbah, R.; Watik, L. El,
Thermodynamic study of anthrone, coumarin and phenazine,
Journal of Thermal Analysis, 1992, 38, 4, 803-809, https://doi.org/10.1007/BF01979412
. [all data]
Watik and Sabbah, 1991
Watik, L.E.; Sabbah, R.,
Etude thermodynamique de la coumarine et de l'anthrone,
Bull. Soc. Chim. Fr., 1991, 128, 344-349. [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]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Sabbah and El Watik, 1992
Sabbah, R.; El Watik, L.,
Thermodynamic study of anthrone, counmarin and phenazine,
J. Therm. Anal., 1992, 38, 803-809. [all data]
Serpinskii, Voitkevich, et al., 1953
Serpinskii, V.V.; Voitkevich, S.A.; Lyuboshits, N.Y.,
Zh. Fiz. Khim., 1953, 27, 1032. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
El Watik and Sabbah, 1991, 2
El Watik, L.; Sabbah, R.,
Thermodynamic study of coumarin and anthrone,
Bull. Soc. Chim. France, 1991, 128, 344-349. [all data]
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
. [all data]
Notes
Go To: Top, Phase change data, References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfusH Enthalpy of fusion ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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