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
Go To: Top, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: 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 |
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
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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, Reaction thermochemistry data, IR Spectrum, Gas Chromatography, 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
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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 | NIST Mass Spectrometry Data Center, 1994 |
| NIST MS number | 134096 |
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
Lee's RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | HP-5 | 142.8 | Wang, Hou, et al., 2007 | 30. m/0.30 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 200. C @ 15. min |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry 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.
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]
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]
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]
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]
Wang, Hou, et al., 2007
Wang, G.; Hou, Z.; Sun, Y.; Liu, Y.; Xie, B.; Liu, S.,
Investigation of pyrolysis behavior of fenoxycarb using PY-GC-MS assisted with chemometric methods,
Chem. Anal., 2007, 52, 141-156. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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