m-Chloroaniline

• Formula: C₆H₆ClN
• Molecular weight: 127.572
• IUPAC Standard InChI: InChI=1S/C6H6ClN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2 Copy

  
• IUPAC Standard InChIKey: PNPCRKVUWYDDST-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-42-9
• 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: Benzenamine, 3-chloro-; Aniline, m-chloro-; m-Aminochlorobenzene; m-Chlorophenylamine; Fast Orange GC Base; Orange GC base; 3-Chloroaniline; 3-Chlorobenzenamine; m-Chloroaminobenzene; Azoic diazo component 2, base; 1-Amino-3-chlorobenzene; 3-Chlooranilinen; 3-Chlorophenylamine; 3-Cloroaniline; m-Chloraniline; Benzeneamine, 3-chloro-; Aniline, 3-chloro-; NSC 17581
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • Gas Chromatography
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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:
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

Reduced pressure boiling point

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of fusion

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 as indicated in comments:
B - John E. Bartmess
ALS - 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

C₆H₅ClN^- +  =

By formula: C₆H₅ClN^- + H⁺ = C₆H₆ClN

=  + 

By formula: C₁₃H₁₀Cl₂N₂O = C₆H₆ClN + C₇H₄ClNO

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% CCl4 FOR 3800-1800, 10% CS2 FOR 1800-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 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

UV/Visible spectrum

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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: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Masalitinova, Oleinikova, et al., 1981
Masalitinova, T.N.; Oleinikova, T.P.; Ryadnenko, V.L.; Kiseleva, N.N.; Lebedeva, N.D., Thermal effects of the hydrogenation of chloronitrobenzenes, J. Appl. Chem. USSR, 1981, 54, 1551-1554, In original 1799. [all data]

Zalikin, Kochetkov, et al., 1965
Zalikin, A.A.; Kochetkov, V.L.; Strepikheev, Yu.A., Some physical and physicochemical constants of m- and p-chloroaniline and of m- and p-chlorophenyl isocyanate, Khim. Prom. (Moscow), 1965, 41, 338. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Pawlowski and Wieckowska, 1980
Pawlowski, W.; Wieckowska, E., Distribution Studies on Ternary System Water--Benzene--Chloro- or Nitroaniline, Pol. J. Chem., 1980, 54, 543. [all data]

Sidgwick and Rubie, 1921
Sidgwick, N.V.; Rubie, H.E., The solubility and volatility of the chloro- and nitro-anilines and of their acetyl derivatives, J. Chem. Soc., 1921, 119, 1013-24. [all data]

Perkin, 1896
Perkin, W.H., LXIX. On Magnetic Rotatory Power, especially of Aromatic Compounds, J. Chem. Soc., 1896, 69, 1025-1257. [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]

Ribeiro da Silva, Gomes, et al., 2005
Ribeiro da Silva, Manuel A.V.; Gomes, José R.B.; Ferreira, Ana I.M.C.L., Experimental and Computational Investigation of the Energetics of the Three Isomers of Monochloroaniline, J. Phys. Chem. B, 2005, 109, 27, 13356-13362, https://doi.org/10.1021/jp0519565 . [all data]

Verevkin and Schick, 2003
Verevkin, Sergey P.; Schick, Christoph, Determination of vapor pressures, enthalpies of sublimation, enthalpies of vaporization, and enthalpies of fusion of a series of chloro-aminobenzenes and chloro-nitrobenzenes, Fluid Phase Equilibria, 2003, 211, 2, 161-177, https://doi.org/10.1016/S0378-3812(03)00181-X . [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]

Dykyj, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Piacente, Scardala, et al., 1985
Piacente, V.; Scardala, P.; Ferro, D.; Gigli, R., Vaporization study of o-, m-, and p-chloroaniline by torsion-weighing effusion vapor pressure measurements, J. Chem. Eng. Data, 1985, 30, 4, 372-376, https://doi.org/10.1021/je00042a002 . [all data]

Khanna, Khetarpal, et al., 1983
Khanna, M.S.; Khetarpal, S.C.; Lal, K.; Bhatnagar, H.L., Thermodynamic studies on melting of some o-, m-, and p-halogen derivatives of aniline, Indian J. Pure Appl. Phys., 1983, 20, 6, 503. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [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]

Lang (editor), 1973
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1973, 18, 41. [all data]

Notes

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Tboil	Boiling point
  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
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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