Benzene, isocyanato-
- Formula: C7H5NO
- Molecular weight: 119.1207
- IUPAC Standard InChI: InChI=1S/C7H5NO/c9-6-8-7-4-2-1-3-5-7/h1-5H
- IUPAC Standard InChIKey: DGTNSSLYPYDJGL-UHFFFAOYSA-N
- CAS Registry Number: 103-71-9
- 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. - Other names: Isocyanic acid, phenyl ester; Carbanil; Isocyanatobenzene; Mondur P; Phenyl carbonimide; Phenyl isocyanate; Phenylcarbimide; Fenylisokyanat; Karbanil; UN 2487; Phenyl ester of isocyanic acid; Additive TI; NSC 74454
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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 | -14.5 ± 1.2 | kJ/mol | Ccr | Steele, Chirico, et al., 1996 | |
| ΔfH°gas | -22.1 | kJ/mol | Cm | Korovin and Margolin, 1976 |
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 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 | -61.1 ± 1.1 | kJ/mol | Ccr | Steele, Chirico, et al., 1996 | ALS |
| ΔfH°liquid | -33.9 ± 1.3 | kJ/mol | Cm | Bykova, Lebedev, et al., 1985 | Different experiment; ALS |
| ΔfH°liquid | -33.9 ± 1.3 | kJ/mol | Ccb | Lebedev, Rabinovich, et al., 1977 | Different experiment; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -3408.07 ± 0.85 | kJ/mol | Ccr | Steele, Chirico, et al., 1996 | ALS |
| ΔcH°liquid | -3455.1 ± 1.3 | kJ/mol | Ccb | Lebedev, Rabinovich, et al., 1977 | Different experiment; ALS |
| ΔcH°liquid | -3402. | kJ/mol | Ccb | Strepikheev, Baranov, et al., 1962 | ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 186.2 | 298.15 | Steele, Chirico, et al., 1993 | DH |
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
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 |
|---|---|---|---|---|---|
| Tc | 675. | K | N/A | Steele, Chirico, et al., 1996, 2 | Uncertainty assigned by TRC = 3. K; fitting parameter in Wagner equation for vapor pressure; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| Pc | 45.40 | bar | N/A | Steele, Chirico, et al., 1996, 2 | Uncertainty assigned by TRC = 3.00 bar; from extrapolation of obs. vapor pressure to Tc; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ρc | 2.928 | mol/l | N/A | Steele, Chirico, et al., 1996, 2 | Uncertainty assigned by TRC = 0.17 mol/l; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 46.5 ± 0.3 | kJ/mol | V | Steele, Chirico, et al., 1996 | ALS |
| ΔvapH° | 46.5 ± 0.3 | kJ/mol | EB | Steele, Chirico, et al., 1996 | Based on data from 329. to 445. K.; AC |
| ΔvapH° | 45.0 | kJ/mol | A | Stephenson and Malanowski, 1987 | Based on data from 283. to 439. K. See also Stull, 1947.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 283.8 to 438.8 | 4.52289 | 1800.757 | -40.303 | Stull, 1947 | 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
3 =
By formula: 3C7H5NO = C21H15N3O3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -51.8 ± 2.9 | kJ/mol | Cm | Bonetskaya, Kravchenko, et al., 1985 | liquid phase; solvent: Diglyme; Trimerization |
| ΔrH° | 80.8 | kJ/mol | Cm | Bykova, Lebedev, et al., 1985 | liquid phase; Different experiment |
+
=
By formula: C7H5NO + C4H10O = C11H15NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -83.9 ± 4.4 | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
| ΔrH° | -105. ± 1. | kJ/mol | Cm | Lovering and Laidler, 1962 | solid phase |
+
=
By formula: C7H5NO + C8H19N = C15H24N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -1088.8 ± 1.7 | kJ/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane |
+
=
By formula: C7H5NO + C6H7N = C13H12N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -82.5 ± 2.0 | kJ/mol | Cm | Kiselev, Malkov, et al., 1989 | liquid phase; solvent: Dioxane |
=
+
By formula: C13H12N2O = C7H5NO + C6H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 181.7 ± 4.2 | kJ/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase; Dissociation |
= 3
By formula: C21H15N3O3 = 3C7H5NO
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -80.8 | kJ/mol | Cm | Bykova, Lebedev, et al., 1985 | solid phase; Different experiment |
=
+
By formula: C9H12N2O = C7H5NO + C2H7N
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 134.2 ± 2.9 | kJ/mol | Eqk | Chimishkyan, Svetlova, et al., 1984 | solid phase |
+
=
By formula: C7H5NO + C6H7N = C13H12N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -89.1 ± 5.1 | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C7H9N = C14H14N2O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -93.0 | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C4H11N = C11H16NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -112. | kJ/mol | Cm | Pannone and Macosko, 1987 | liquid phase |
+
=
By formula: C7H5NO + C9H10O2 = C16H15NO3
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -196.7 | kJ/mol | Cm | Lebedev, Bykova, et al., 1988 | liquid phase |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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 | NIST Mass Spectrometry Data Center, 1994 |
| NIST MS number | 134096 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, 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.
Steele, Chirico, et al., 1996
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.; Tasker, I.R.,
Thermodynamic properties and ideal-gas enthalpies of formation for cyclohexene, phthalan (2,5-dihydrobenzo-3,4-furan), isoxazole, octylamine, dioctylamine, trioctylamine, phenyl isocyanate, and 1,4,5,6-tetrahydropyrimidine,
J. Chem. Eng. Data, 1996, 41, 1269-1284. [all data]
Korovin and Margolin, 1976
Korovin, A.I.; Margolin, L.N.,
Thermodynamic functions of phenyl isocyanate,
Zh. Fiz. Khim., 1976, 50, 2923-29. [all data]
Bykova, Lebedev, et al., 1985
Bykova, T.A.; Lebedev, B.V.; Kiparisova, E.G.; Tarasov, E.N.; Frenkel, Ts.M.; Pankratov, V.A.; Vinogradova, S.V.; Korshank, V.V.,
Thermodynamics of phenyl isocyanate, the process of its cyclotrimerization, and the triphenyl isocyanurate that is formed, in the 0-330°K interval,
J. Gen. Chem. USSR, 1985, 55, 2303-2308. [all data]
Lebedev, Rabinovich, et al., 1977
Lebedev, B.V.; Rabinovich, I.B.; Kiparisova, E.G.; Evstropov, A.A.; Korshak, V.V.; Pankratov, V.A.; Larina, L.F.,
Thermodynamics of the polycyclotrimerization of aromatic dicyanates and diisocyanates,
Dokl. Phys. Chem. (Engl. Transl.), 1977, 237, 1081-1084, In original 383. [all data]
Strepikheev, Baranov, et al., 1962
Strepikheev, Yu.A.; Baranov, Yu.I.; Burmistrova, O.A.,
Determination of the heats of combustion and the heat capacities of several mono- and di-isocyanates,
Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 1962, 5, 387-390. [all data]
Steele, Chirico, et al., 1993
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Tasker, I.R.,
Determination of ideal gas enthalpies of formation for key compounds the 1991 project results,
DIPPR Project, 1993, 871, NIPER-716. [all data]
Steele, Chirico, et al., 1996, 2
Steele, W.V.; Chirico, R.D.; Knipmeyer, S.E.; Nguyen, A.; Smith, N.K.; Tasker, I.R.,
Thermodynamic Properties and Ideal-Gas Enthalpies of Formation for Dioctylamine, trioctylamine, Phenyl Isocyanate, and 1,4,5,6-Tetrahydropyrimidine,
J. Chem. Eng. Data, 1996, 41, 1269-84. [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]
Bonetskaya, Kravchenko, et al., 1985
Bonetskaya, A.K.; Kravchenko, M.A.; Frenkel, Ts.M.; Pankratov, V.A.; Vinogradova, S.V.; Korshak, V.V.,
Kinetics and heat of cyclotrimerization of aryl and alkyl isocyanates,
Vysokomol. Soedin., Ser. A, 1985, 27, 1269-1273. [all data]
Pannone and Macosko, 1987
Pannone, M.C.; Macosko, C.W.,
Kinetics of isocyanate amine reactions,
J. Appl. Polym. Sci., 1987, 34, 2409-2432. [all data]
Lovering and Laidler, 1962
Lovering, E.G.; Laidler, K.J.,
Thermochemical studies of some alcohol-isocyanate reactions,
Can. J. Chem., 1962, 40, 26-30. [all data]
Kiselev, Malkov, et al., 1989
Kiselev, V.D.; Malkov, V.B.; Murzin, D.G.; Shakirov, I.M.; Konovalov, A.I.,
Thermochemical study of the reaction of isocyanate with amines,
Dokl. Phys. Chem. (Engl. Transl.), 1989, 308, 711-713, In original 111. [all data]
Chimishkyan, Svetlova, et al., 1984
Chimishkyan, A.L.; Svetlova, L.P.; Leonova, T.V.; Gluyaev, N.D.,
Thermal decomposition of substituted ureas,
J. Gen. Chem. USSR, 1984, 54, 1317-1320. [all data]
Lebedev, Bykova, et al., 1988
Lebedev, B.V.; Bykova, T.A.; Kiparisova, E.G.; Frenkel, Ts.M.; Fainleib, A.M.; Pankratov, V.A.,
Thermodynamics of phenyl glycidyl ether and its reactions with diphenylcarbodiimide and phenyl isocyanate with the formation of iminooxazolidine and oxazolidinone in the 0-330 K range,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1988, 1082-10. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid Pc Critical pressure Tc Critical temperature 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 at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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