1,3-Dioxane, 4-methyl-

• Formula: C₅H₁₀O₂
• Molecular weight: 102.1317
• IUPAC Standard InChI: InChI=1S/C5H10O2/c1-5-2-3-6-4-7-5/h5H,2-4H2,1H3 Copy

  
• IUPAC Standard InChIKey: INCCMBMMWVKEGJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 1120-97-4
• 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: m-Dioxane, 4-methyl-; 4-Methyl-m-dioxane; 4-Methyl-1,3-dioxane
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
AC - William E. Acree, Jr., James S. Chickos

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 compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard

Ionization 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

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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Normal alkane RI, non-polar column, isothermal

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

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Normal alkane RI, polar column, custom temperature program

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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.

Pihlaja and Luoma, 1968
Pihlaja, K.; Luoma, S., Heats of formation and conformational energies of 1,3-dioxane and its methyl homologues, Acta Chem. Scand., 1968, 22, 2401-2414. [all data]

Pihlaja and Heikkila, 1967
Pihlaja, K.; Heikkila, J., The configurations of isomeric 2,2,4,6-tetramethyl-1,3-dioxanes, Acta Chem. Scand., 1967, 21, 2430-2434. [all data]

Skuratov, Kozina, et al., 1957
Skuratov, S.M.; Kozina, M.L.; Shteher, S.M.; Varushyenko, R.M., The heats of combustion of several purified compounds, Thermochem. Bull. (Moscow State Univ.), March, 1957, 36-37. [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]

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

Farberov and Speranskaya, 1958
Farberov, M.I.; Speranskaya, V.A., Synthesis of β-Chloro Substituted Alcohols and Their Transformations, Zh. Obshch. Khim., 1958, 28, 2151. [all data]

Verevkin, Peng, et al., 1998
Verevkin, S.P.; Peng, W.-H.; Beckhaus, H.D.; Rücuardt, C., Geminal substituent effects. 16. Does the anomeric effect in ketals depend on the hybridization of the central carbon atom?, Eur. J. Org. Chem., 1998, 11, 2323. [all data]

Verevkin, 2002
Verevkin, Sergey P., Improved Benson Increments for the Estimation of Standard Enthalpies of Formation and Enthalpies of Vaporization of Alkyl Ethers, Acetals, Ketals, and Ortho Esters, J. Chem. Eng. Data, 2002, 47, 5, 1071-1097, https://doi.org/10.1021/je020023o . [all data]

Asfandiarov and Zykov, 1983
Asfandiarov, N.L.; Zykov, B.G., Photoelectron spectra of methyl-substituted 1,3-Dioxanes, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1983, 10, 2069, In original 2293. [all data]

Misharina, Golovnya, et al., 1993
Misharina, T.A.; Golovnya, R.V.; Beletsky, I.V., Sorption properties of heterocyclic compounds differing by heteroatom in capillary gas chromatography, Russ. Chem. Bull. (Engl. Transl.), 1993, 42, 7, 1167-1170, https://doi.org/10.1007/BF00701998 . [all data]

Bogoslovsky, Anvaer, et al., 1978
Bogoslovsky, Yu.N.; Anvaer, B.I.; Vigdergauz, M.S., Chromatographic constants in gas chromatography (in Russian), Standards Publ. House, Moscow, 1978, 192. [all data]

Kurdina, Markovich, et al., 1969
Kurdina, Z.G.; Markovich, V.E.; Sakharov, V.M., Gas chromatography of cyclic O-containing compounds in Gas chromatography, Issue # 10, NIITEKhim, Moscow, 1969, 128-133. [all data]

Vinogradov, 2004
Vinogradov, B.A., Production, composition, properties and application of essential oils, 2004, retrieved from http://viness.narod.ru. [all data]

Notes

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• Symbols used in this document:
  

  Tboil	Boiling point
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation 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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