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)
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • UV/Visible spectrum
  • 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

References

Go To: Top, 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.

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]

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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