Benzenamine, 2,4-dimethyl-

• Formula: C₈H₁₁N
• Molecular weight: 121.1796
• IUPAC Standard InChI: InChI=1S/C8H11N/c1-6-3-4-8(9)7(2)5-6/h3-5H,9H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: CZZZABOKJQXEBO-UHFFFAOYSA-N Copy
• CAS Registry Number: 95-68-1
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: 2,4-Xylidine; m-Xylidine; 1-Amino-2,4-dimethylbenzene; 2,4-Dimethylaniline; 4-Amino-1,3-dimethylbenzene; 4-Amino-1,3-xylene; 2,4-Dimethylbenzeneamine; m-4-Xylidine; Aniline, 2,4-dimethyl-; 2-Methyl-p-toluidine; 2,4-Dimethylbenzenamine; 4-Amino-3-methyltoluene; 4-Methyl-o-toluidine; 2,4-Dimethylphenylamine; 2,4-Xylylamine; NSC 7640
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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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 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

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• SOLUTION (10% IN CCl4 FOR 3800-1335, 10% IN CS2 FOR 1335-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 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

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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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.

Lemoult, 1907
Lemoult, M.P., Recherches theoriques et experimentales sur les chaleurs de combustion et de formation des composes organiques, Ann. Chim. Phys., 1907, 12, 395-432. [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]

Buehler, Wood, et al., 1932
Buehler, C.A.; Wood, J.H.; Hull, D.C.; Erwin, E.C., A Study of Molecular Organic Compounds. IV. The Molecular Organic Compounds of Phenol, their Parachors and Refractivities, J. Am. Chem. Soc., 1932, 54, 2398. [all data]

Witschonke, 1954
Witschonke, C.R., Freezing point and purity data for some organic compounds, Anal. Chem., 1954, 26, 562-4. [all data]

Birch, Dean, et al., 1949
Birch, S.F.; Dean, R.A.; Fidler, F.A.; Lowry, R.A., The preparation of the c(10) monocyclic aromatic hydrocarbons, J. Am. Chem. Soc., 1949, 71, 1362. [all data]

Verevkin, 1997
Verevkin, Sergey P., Thermochemistry of amines: experimental standard molar enthalpies of formation of some aliphatic and aromatic amines, The Journal of Chemical Thermodynamics, 1997, 29, 8, 891-899, https://doi.org/10.1006/jcht.1997.0212 . [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]

Farrell and Newton, 1966
Farrell, P.G.; Newton, J., Ionization potentials of primary aromatic amines and aza-hydrocarbons, Tetrahedron Lett., 1966, 5517. [all data]

Szepes, Distefano, et al., 1974
Szepes, L.; Distefano, G.; Pignataro, S., Steric inhibition of resonance in acetanilides by UV photoelectron spectroscopy, Ann. Chim., 1974, 64, 159. [all data]

Kuhn, 2001
Kuhn, E.R., Selectivity vs. polarity: the fundamentals of chromatographic separation, J. Sep. Sci., 2001, 24, 6, 473-476, https://doi.org/10.1002/1615-9314(20010601)24:6<473::AID-JSSC473>3.0.CO;2-Y . [all data]

Cha and Lee, 1994
Cha, K.-W.; Lee, D.-J., Prediction of retention indices of various compounds in gas-liquid chromatography, J. Korean Chem. Soc., 1994, 38, 2, 108-120, retrieved from http://journal.kcsnet.or.kr/publi/dh/dh94n2/108.pdf. [all data]

Hedin, Thopson, et al., 1972
Hedin, P.A.; Thopson, A.C.; Gueldner, R.C.; Minyard, J.P., Volatile constituents of the boll weevil, J. Insect. Physiol., 1972, 18, 1, 79-86, https://doi.org/10.1016/0022-1910(72)90066-2 . [all data]

Still, Evans, et al., 1972
Still, R.H.; Evans, M.B.; Whitehead, A., Thermal Degradation of Polymers. V. Vacuum Pyrolysis of Poly (p-N,N-dimethylaminostyrene) . The Products Volatile at Pyrolysis Temperature, Liquid or Gaseous at Room Temperature, J. Appl. Polym. Sci., 1972, 16, 12, 3207-3221, https://doi.org/10.1002/app.1972.070161213 . [all data]

Sun and Stremple, 2003
Sun, G.; Stremple, P., Retention index characterization of flavor, fragrance, and many other compounds on DB-1 and DB-XLB, 2003, retrieved from http://www.chem.agilent.com/cag/cabu/pdf/b-0279.pdf. [all data]

Gautzsch and Zinn, 1996
Gautzsch, R.; Zinn, P., Use of incremental models to estimate the retention indexes of aromatic compounds, Chromatographia, 1996, 43, 3/4, 163-176, https://doi.org/10.1007/BF02292946 . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Okumura, 1991
Okumura, T., retention indices of environmental chemicals on methyl silicone capillary column, Journal of Environmental Chemistry (Japan), 1991, 1, 2, 333-358, https://doi.org/10.5985/jec.1.333 . [all data]

Notes

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• Symbols used in this document:
  

  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
  ΔvapH	Enthalpy of vaporization

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