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 Copy

  
• IUPAC Standard InChIKey: DGTNSSLYPYDJGL-UHFFFAOYSA-N Copy
• 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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• Information on this page:
  • 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)
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

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

Constant pressure heat capacity of liquid

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

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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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

 +  =

By formula: C₇H₅NO + C₄H₁₀O = C₁₁H₁₅NO₂

 +  =

By formula: C₇H₅NO + C₈H₁₉N = C₁₅H₂₄N₂O

 +  =

By formula: C₇H₅NO + C₆H₇N = C₁₃H₁₂N₂O

=  + 

By formula: C₁₃H₁₂N₂O = C₇H₅NO + C₆H₇N

= 3

By formula: C₂₁H₁₅N₃O₃ = 3C₇H₅NO

=  + 

By formula: C₉H₁₂N₂O = C₇H₅NO + C₂H₇N

 +  =

By formula: C₇H₅NO + C₆H₇N = C₁₃H₁₂N₂O

 +  =

By formula: C₇H₅NO + C₇H₉N = C₁₄H₁₄N₂O

 +  =

By formula: C₇H₅NO + C₄H₁₁N = C₁₁H₁₆NO₂

 +  =

By formula: C₇H₅NO + C₉H₁₀O₂ = C₁₆H₁₅NO₃

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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to C₇H₅NO⁺ (ion structure unspecified)

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); PERKIN-ELMER 521 (GRATING); DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

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

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), 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]

Kobayashi and Nagakura, 1975
Kobayashi, T.; Nagakura, S., Photoelectron spectra of phenyl isocyanates and phenyl isothio- cyanate, J. Electron Spectrosc. Relat. Phenom., 1975, 7, 488. [all data]

Compernolle and DeSchryver, 1975
Compernolle, F.; DeSchryver, F., Nonconcerted cycloreversion by electron impact of substituted 2,4-azetidinediones. Relations between the mass spectral and photochemical reactions, J. Am. Chem. Soc., 1975, 97, 3909. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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), References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  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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