Benzene, 1,2-dimethoxy-

• Formula: C₈H₁₀O₂
• Molecular weight: 138.1638
• IUPAC Standard InChI: InChI=1S/C8H10O2/c1-9-7-5-3-4-6-8(7)10-2/h3-6H,1-2H3 Copy

  
• IUPAC Standard InChIKey: ABDKAPXRBAPSQN-UHFFFAOYSA-N Copy
• CAS Registry Number: 91-16-7
• 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: Benzene, o-dimethoxy-; o-Dimethoxybenzene; O,O-Dimethyl catechol; Pyrocatechol dimethyl ether; Veratrol; Veratrole; 1,2-Dimethoxybenzene; Dimethylether pyrokatechinu; Orthodimethoxybenzene; 2-Methoxyanisole; Catechol dimethyl ether; NSC 16934; Methylguaiacol; 1,2-Dimethoxybenzene (veratroI); 1,2-Dimethoxybenzene (veratrole); 1,2-Dimethoxybenzene (Veratrol)
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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
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Reduced pressure boiling point

Enthalpy of vaporization

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
LL - Sharon G. Lias and Joel F. Liebman

Ionization energy determinations

Appearance energy determinations

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

Gas Phase Spectrum

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Additional Data

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

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

Cass, Fletcher, et al., 1958
Cass, R.C.; Fletcher, S.E.; Mortimer, C.T.; Quincey, P.G.; Springall, H.D., Heats of combustion and molecular structure. Part VI. The structure of some cyclic ethers of o-dihydroxybenzene, J. Chem. Soc., 1958, 2595-2597. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M., Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Lecat, 1927
Lecat, M., New binary azeotropes: 6th list, Ann. Soc. Sci. Bruxelles, Ser. B, 1927, 47, 63-71. [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]

Deffet, 1940
Deffet, L., Piezometric Research. Temperatures of Fusion and Transformation, Bull. Soc. Chim. Belg., 1940, 49, 223. [all data]

Cauwood and Turner, 1915
Cauwood, J.D.; Turner, W.E.S., XXXI. The Dielectric Constants of Some Organic Solvents at their Melting or Boiling Points, J. Chem. Soc., Trans., 1915, 107, 276. [all data]

Louguinine and Dupont, 1911
Louguinine, W.; Dupont, G., The heat of fusion of substances which melt at ordinary temperatures., Bull. Soc. Chim. Fr., 1911, 9, 219-224. [all data]

Matos, Miranda, et al., 2000
Matos, M.A.R.; Miranda, M.S.; Morais, V.M.F., Calorimetric and Theoretical Determination of Standard Enthalpies of Formation of Dimethoxy- and Trimethoxybenzene Isomers, J. Phys. Chem. A, 2000, 104, 40, 9260-9265, https://doi.org/10.1021/jp001928g . [all data]

Lee, Su, et al., 2004
Lee, Ming-Jer; Su, Chang-Ching; Lin, Ho-mu, Isothermal Vapor-Liquid Equilibria for Binary Mixtures Composed of the Closely Boiling Compounds 1,2-Dimethoxybenzene and 2-Methoxyphenol with an Adducted Agent: tert -Butanol or Morpholine, J. Chem. Eng. Data, 2004, 49, 3, 588-593, https://doi.org/10.1021/je0302349 . [all data]

Domelsmith and Houk, 1978
Domelsmith, L.N.; Houk, K.N., Photoelectron spectroscopic studies of hallucinogens: The use of ionization potentials in QSAR, NIDA Res. Monogr., 1978, 22, 423. [all data]

Voigt and Reid, 1964
Voigt, E.M.; Reid, C., Ionization potentials of substituted benzenes and their charge-transfer spectra with tetracyanoethylene, J. Am. Chem. Soc., 1964, 86, 3930. [all data]

Anderson, Kollman, et al., 1979
Anderson, G.M., III; Kollman, P.A.; Domelsmith, L.N.; Houk, K.N., Methoxy group nonplanarity in o-dimethoxybenzenes. Simple predictive models for conformations and rotational barriers in alkoxyaromatics, J. Am. Chem. Soc., 1979, 101, 2344. [all data]

Mori, Ogawa, et al., 1992
Mori, Y.; Ogawa, Y.; Shinoda, H.; Kitagawa, T., Two competing fragmentation processes in dimethoxybenzenes depending on their positional isomers: Elimination of CH₃ and CH_nO (n = 1-3) and formation of methoxycyclopentadienyl and protonated phenol ions, Org. Mass Spectrom., 1992, 27, 578. [all data]

Lang (editor), 1972
Lang (editor), L., Absorption Spectra in the Ultraviolet and Visible Region, 1972, 16, 123. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  ΔcH°liquid	Enthalpy of combustion of liquid 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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