Thiophene, 2,5-dimethyl-

• Formula: C₆H₈S
• Molecular weight: 112.193
• IUPAC Standard InChI: InChI=1S/C6H8S/c1-5-3-4-6(2)7-5/h3-4H,1-2H3 Copy

  
• IUPAC Standard InChIKey: GWQOOADXMVQEFT-UHFFFAOYSA-N Copy
• CAS Registry Number: 638-02-8
• 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: 2,5-Dimethylthiophene
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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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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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

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

Enthalpy of phase transition

Entropy of phase transition

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
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

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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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

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

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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Kovats' RI, polar column, temperature ramp

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

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

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

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Van Den Dool and Kratz RI, polar column, custom temperature program

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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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Normal alkane RI, polar column, temperature ramp

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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.

Carlson and Westrum, 1965
Carlson, H.G.; Westrum, E.F., Jr., 2,5-Dimethylthiophene. Heat capacities and thermodynamic properties from 5 to 300 K and fusion of stable and metastable phases, J. Phys. Chem., 1965, 68, 1524-1530. [all data]

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Carlson and Westrum, 1965, 2
Carlson, H.G.; Westrum, E.F., 2,5-Dimethylthiopnehe. Heat Capacities and Thermodynamic Properties from 5 to 300 K and Fusion of Stable and Metastable Phases, J. Phys. Chem., 1965, 69, 1524. [all data]

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Agrawal, Tesarík, et al., 1972
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Galt and MacLeod, 1984
Galt, A.M.; MacLeod, G., Headspace sampling of cooked beef aroma using Tenax GC, J. Agric. Food Chem., 1984, 32, 1, 59-64, https://doi.org/10.1021/jf00121a016 . [all data]

Elmore, Campo, et al., 2002
Elmore, J.S.; Campo, M.M.; Enser, M.; Mottram, D.S., Effect of lipid composition on meat-like model systems containing cysteine, ribose, and polyunsaturated fatty acids, J. Agric. Food Chem., 2002, 50, 5, 1126-1132, https://doi.org/10.1021/jf0108718 . [all data]

Ames, Guy, et al., 2001
Ames, J.M.; Guy, R.C.E.; Kipping, G.J., Effect of pH and temperature on the formation of volatile compounds in cysteine/reducing sugar/starch mixtures during extrusion cooking, J. Agric. Food Chem., 2001, 49, 4, 1885-1894, https://doi.org/10.1021/jf0012547 . [all data]

Whitfield and Mottram, 2001
Whitfield, F.B.; Mottram, D.S., Heterocyclic volatiles formed by heating cysteine or hydrogen sulfide with 4-hydroxy-5-methyl-3(2H)-furanone at pH 6.5, J. Agric. Food Chem., 2001, 49, 2, 816-822, https://doi.org/10.1021/jf0008644 . [all data]

Madruga and Mottram, 1998
Madruga, M.S.; Mottram, D.S., The effect of pH on the formation of volatile compounds produced by heating a model system containing 5'-imp and cysteine, J. Braz. Chem. Soc., 1998, 9, 3, 261-271, https://doi.org/10.1590/S0103-50531998000300010 . [all data]

Misharina, Golovnya, et al., 1994
Misharina, T.A.; Golovnya, R.V.; Strashnenko, E.S.; Medvedeva, I.B., Sorbtion-structural mass-spectrometric characteristics of volatile components of model systems and flavor compounds with meat odor, Zh. Anal. Khim., 1994, 49, 7, 722-728. [all data]

Yu, Lin, et al., 1994
Yu, T.-H.; Lin, L.-Y.; Ho, C.-T., Volatile compounds of blanched, fried blanched, and baked blanched garlic slices, J. Agric. Food Chem., 1994, 42, 6, 1342-1347, https://doi.org/10.1021/jf00042a018 . [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]

Kuo and Ho, 1992
Kuo, M.-C.; Ho, C.-T., Volatile constituents of the distilled oils of Welsh onions (Allium fistulosum L. variety Maichuon) and scallions (Allium fistulosum L. variety Caespitosum), J. Agric. Food Chem., 1992, 40, 1, 111-117, https://doi.org/10.1021/jf00013a021 . [all data]

Misharina, Golovnya, et al., 1992
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Zhang and Ho, 1991
Zhang, Y.; Ho, C.-T., Comparison of the volatile compounds formed from the thermal reaction of glucose with cysteine and glutathione, J. Agric. Food Chem., 1991, 39, 4, 760-763, https://doi.org/10.1021/jf00004a029 . [all data]

Moon, Cliff, et al., 2006
Moon, S.-Y.; Cliff, M.A.; Li-Chan, E.C.Y., Odour-active components of simulated beef flavour analysed by solid phase microextraction and gas chromatography-mass spectrometry and -olfactometry, Food Res. Int., 2006, 39, 3, 294-308, https://doi.org/10.1016/j.foodres.2005.08.002 . [all data]

Elmore, Mottram, et al., 2000
Elmore, J.S.; Mottram, D.S.; Enser, M.; Wood, J.D., The effects of diet and breed on the volatile compounds of cooked lamb, Meat Sci., 2000, 55, 2, 149-159, https://doi.org/10.1016/S0309-1740(99)00137-0 . [all data]

Elmore, Mottram, et al., 1999
Elmore, J.S.; Mottram, D.S.; Enser, M.; Wood, J.D., Effect of the polyunsaturated fatty acid composition of beef muscle on the profile of aroma volatiles, J. Agric. Food Chem., 1999, 47, 4, 1619-1625, https://doi.org/10.1021/jf980718m . [all data]

Mahadevan and Farmer, 2006
Mahadevan, K.; Farmer, L., Key Odor Impact Compounds in Three Yeast Extract Pastes, J. Agric. Food Chem., 2006, 54, 19, 7242-7250, https://doi.org/10.1021/jf061102x . [all data]

Nielsen, Larsen, et al., 2004
Nielsen, G.S.; Larsen, L.M.; Poll, L., Formation of aroma compounds during long-term frozen storage of unblanched leek (Allium ampeloprasum Var. Bulga) as affected by packaging atmosphere and slice thickness, J. Agric. Food Chem., 2004, 52, 5, 1234-1240, https://doi.org/10.1021/jf0306183 . [all data]

Nielsen, Larsen, et al., 2004, 2
Nielsen, G.S.; Larsen, L.M.; Poll, L., Impact of blanching and packaging atmosphere on the formation of aroma compounds during long-term frozen storage of leek (Allium ampeloprasum Var. Bulga) slices, J. Agric. Food Chem., 2004, 52, 15, 4844-4852, https://doi.org/10.1021/jf049623c . [all data]

Nielsen and Poll, 2004
Nielsen, G.S.; Poll, L., Determination of odor active aroma compounds in freshly cut leek (Allium ampeloprasum Var. Bulga) and in long-term stored frozen unblanched and blanched leek slices by gas chromatography olfactometry analysis, J. Agric. Food Chem., 2004, 52, 6, 1642-1646, https://doi.org/10.1021/jf030682k . [all data]

Yu, Wu, et al., 1993
Yu, T.-H.; Wu, C.-M.; Ho, C.-T., Volatile compounds of deep-oil fried, microwave-heated, and oven-baked garlic slices, J. Agric. Food Chem., 1993, 41, 5, 800-805, https://doi.org/10.1021/jf00029a023 . [all data]

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Whitfield, F.B.; Mottram, D.S.; Brock, S.; Puckey, D.J.; Salter, L.J., Effect of Phospholipid on the Formation of Volatile Heterocyclic Compounds in Heated Aqueous Solutions of Amino Acids and Ribose, J. Sci. Food Agric., 1988, 42, 3, 261-272, https://doi.org/10.1002/jsfa.2740420309 . [all data]

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Sugisawa, H.; Nakamura, K.; Tamura, H., The aroma profile of the volatile in marine green algae (Ulva pertusa), Food Reviews International, 1990, 6, 4, 573-589, https://doi.org/10.1080/87559129009540893 . [all data]

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Chyau and Mau, 2001
Chyau, C.-C.; Mau, J.-L., Effects of various oils on volatile compounds of deep-fried shallot flavouring, Food Chem., 2001, 74, 1, 41-46, https://doi.org/10.1016/S0308-8146(00)00336-8 . [all data]

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Umano, K.; Hagi, Y.; Nakahara, K.; Shyoji, A.; Shibamoto, T., Volatile chemicals formed in the headspace of a heated D-glucose/L-cysteine Maillard model system, J. Agric. Food Chem., 1995, 43, 8, 2212-2218, https://doi.org/10.1021/jf00056a046 . [all data]

Shibamoto and Russell, 1977
Shibamoto, T.; Russell, G.F., A study of the volatiles isolated from a D-glucose-hydrogen sulfide-ammonia model system, J. Agric. Food Chem., 1977, 25, 1, 109-112, https://doi.org/10.1021/jf60209a054 . [all data]

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Shibamoto, T.; Russell, G.F., Study of meat volatiles associated with aroma generated in a D-glucose-hydrogen sulfide-ammonia model system, J. Agric. Food Chem., 1976, 24, 4, 843-846, https://doi.org/10.1021/jf60206a047 . [all data]

Gyawalia, Seo, et al., 2006
Gyawalia, R.; Seo, H.-Y.; Lee, H.-J.; Song, H.-P.; Kim, D.-H.; Byun, M.-W.; Kim, K.-S., Effect of γ-irradiation on volatile compounds of dried Welsh onion (Allium fistulosum L.), Radiat. Phys. Chem., 2006, 75, 2, 322-328, https://doi.org/10.1016/j.radphyschem.2005.07.001 . [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
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfusH	Enthalpy of fusion
  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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