1,2-Butadiene, 3-methyl-

• Formula: C₅H₈
• Molecular weight: 68.1170
• IUPAC Standard InChI: InChI=1S/C5H8/c1-4-5(2)3/h1H2,2-3H3 Copy

  
• IUPAC Standard InChIKey: PAKGDPSCXSUALC-UHFFFAOYSA-N Copy
• CAS Registry Number: 598-25-4
• 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: 1,1-Dimethylallene; 1,1-Dimethylallylene; 2-Methyl-2,3-butadiene; 3-Methyl-1,2-butadiene; 3,3-Dimethylallene; CH2=C=C(CH3)2; 3-methylbuta-1,2-diene
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Microwave spectra (on physics lab web site)
  • 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

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

Entropy of fusion

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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C₅H₈⁺ (ion structure unspecified)

Ionization energy determinations

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.

Good, 1969
Good, W.D., 3-Methyl-1,2-butadiene: Enthalpies of combustion and formation, J. Chem. Eng. Data, 1969, 14, 480-481. [all data]

Messerly, Todd, et al., 1970
Messerly, J.F.; Todd, S.S.; Guthrie, G.B., Chemical thermodynamic properties of the pentadienes, J. Chem. Eng. Data, 1970, 15, 227-232. [all data]

Streiff, Schultz, et al., 1957
Streiff, A.J.; Schultz, L.H.; Hulme, A.R.; Tucker, J.A.; Krouskop, N.C.; Rossini, F.D., Purification, Purity, and Freezing Points of 20 API Standard API Research Hydrocarbons, Anal. Chem., 1957, 29, 361. [all data]

Messerly, Todd, et al., 1970, 2
Messerly, J.F.; Todd, S.S.; Guthrie, G.B., Chemical thermodynamic properties of the pentadienes. Third law studies., J. Chem. Eng. Data, 1970, 15, 227-32. [all data]

Steele, Chirico, et al., 1990
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K., Determination of ideal-gas enthalpies of formation for key compounds, Am. Inst. Chem. Eng. Symp. Ser. (AIChE Symp. Ser.), 1990, 138-154. [all data]

Reid, 1972
Reid, Robert C., Handbook on vapor pressure and heats of vaporization of hydrocarbons and related compounds, R. C. Wilhort and B. J. Zwolinski, Texas A Research Foundation. College Station, Texas(1971). 329 pages.$10.00, AIChE J., 1972, 18, 6, 1278-1278, https://doi.org/10.1002/aic.690180637 . [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]

Osborn and Douslin, 1969
Osborn, Ann G.; Douslin, Donald R., Vapor pressure relations for the seven pentadienes, J. Chem. Eng. Data, 1969, 14, 2, 208-209, https://doi.org/10.1021/je60041a010 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

Harris, McKinnon, et al., 1979
Harris, D.; McKinnon, S.; Boyd, R.K., The origins of the base peak in the electron impact spectrum of limonene, Org. Mass Spectrom., 1979, 14, 265. [all data]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Brogli, Crandall, et al., 1973
Brogli, F.; Crandall, J.K.; Heilbronner, E.; Kloster-Jensen, E.; Sojka, S.A., The photoelectron spectra of methyl-substituted allenes and of tetramethyl-bisallenyl, J. Electron Spectrosc. Relat. Phenom., 1973, 2, 455. [all data]

Notes

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy 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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