2,6-Xylidine

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

  
• IUPAC Standard InChIKey: UFFBMTHBGFGIHF-UHFFFAOYSA-N Copy
• CAS Registry Number: 87-62-7
• 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, 2,6-dimethyl-; 1-Amino-2,6-dimethylbenzene; 2-Amino-m-xylene; 2-Amino-1,3-dimethylbenzene; 2-Amino-1,3-xylene; 2,6-Dimethylaniline; 2,6-Dimethylbenzenamine; o-Xylidine; Aniline, 2,6-dimethyl-; NCI-C56188; 2,6-Xylylamine; 2,6-Dimethylphenylamine; NSC 7098
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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)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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: 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos

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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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:
HL - Edward P. Hunter and Sharon G. Lias
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

Ionization energy determinations

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID (NEAT); BECKMAN IR-4 (HYBRID PRISM-GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY (ADJUSTED 0.035-0.03-0); 2 cm^-1 resolution
• SOLUTION (10% IN CCl4 FOR 5000-1350 CM^-1, 10% IN CS2 FOR 1350-625 CM^-1); Not specified, most likely a prism, grating, or hybrid spectrometer.; 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

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

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, isothermal

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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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), UV/Visible spectrum, 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., 1986
Steele, W.V.; Chirico, R.D.; Collier, W.B.; Hossenlopp, I.A.; Nguyen, A.; Strube, M.M., Thermochemical and thermophysical properties of organic nitrogen compounds found in fossil materials, NIPER Report, 1986, 188, 112p. [all data]

Frinton Laboratories Inc., 1986
Frinton Laboratories Inc., Catalog Number 11, Frinton Laboratories Inc., Vineland, NJ, 1986, 99. [all data]

Schwartzman and Corson, 1954
Schwartzman, L.H.; Corson, B.B., Steric Hinderance I. 2,6-Dimethylacetophenone and 2,6-Dimethylstyrene, J. Am. Chem. Soc., 1954, 76, 781. [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, 2000
Verevkin, Sergey P., Thermochemical study of the ortho interactions in alkyl substituted anilines, The Journal of Chemical Thermodynamics, 2000, 32, 2, 247-259, https://doi.org/10.1006/jcht.1999.0587 . [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]

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy Part 3. Anilines, Phenols and Related Compounds, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 521. [all data]

Cowling and Johnstone, 1973
Cowling, S.A.; Johnstone, R.A.W., Photoelectron spectroscopy: The effects of steric inhibition to resonance in anilines, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 161. [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]

Lang (editor), 1968
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1968, 10, 65. [all data]

Berezkin, Korolev, et al., 2000
Berezkin, V.G.; Korolev, A.A.; Malyukova, I.V., A comparative analysis of retention values obtained on fused silica capillary columns from various manufacturers, Analusis, 2000, 28, 2, 132-135, https://doi.org/10.1051/analusis:2000105 . [all data]

Malyukova, Berezkin, et al., 1997
Malyukova, I.V.; Berezkin, V.G.; Kramers, K.; Jansen, H.G., Capillary chromatrography of hydrocarbons and their derivatives. Use of sulphur hexafluoride as the carrier gas, Pet. Chem. USSR (Engl. Transl.), 1997, 37, 3, 265-272. [all data]

Juvancz, Cserháti, et al., 1994
Juvancz, Z.; Cserháti, T.; Markides, K.E.; Bradshaw, J.S.; Lee, M.L., Characterization of some new polysiloxane stationary phases by principal component analysis, Chromatographia, 1994, 38, 3/4, 227-231, https://doi.org/10.1007/BF02290341 . [all data]

Farkas, Sojak, et al., 1989
Farkas, P.; Sojak, L.; Kovac, M.; Janak, J., Interface Adsorption and Reproducibility of Retention Indices in Glass Capillary Columns with Dimethylpolysiloxane Stationary Phases Cross-Linked by γ-Irradiation, J. Chromatogr., 1989, 471, 251-261, https://doi.org/10.1016/S0021-9673(00)94173-6 . [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]

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]

Berezkin, Korolev, et al., 1998
Berezkin, V.G.; Korolev, A.A.; Malyukova, I.V., Dependence of the relative retention of compounds on the average pressure of helium as a carrier gas in capillary GLC, Russ. Chem. Bull. (Engl. Transl.), 1998, 47, 2, 307-309, https://doi.org/10.1007/BF02498955 . [all data]

Berezkin and Korolev, 1985
Berezkin, V.G.; Korolev, A.A., Investigation of the role of adsorption at the stationary phase interface in capillary columns with cross-linked phases, Chromatographia, 1985, 20, 8, 482-486, https://doi.org/10.1007/BF02344790 . [all data]

Kim, Kim, et al., 1993
Kim, K.-R.; Kim, J.-H.; Park, H.-K.; Oh, C.-H., Dual capillary column system for the qualitative gas chromatography: 2. Comparison between splitless and on-column injection modes, Bull. Korean Chem. Soc., 1993, 14, 2, 250-255. [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]

Waggott and Davies, 1984
Waggott, A.; Davies, I.W., Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  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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