2-Butene, 2-methyl-

• Formula: C₅H₁₀
• Molecular weight: 70.1329
• IUPAC Standard InChI: InChI=1S/C5H10/c1-4-5(2)3/h4H,1-3H3 Copy

  
• IUPAC Standard InChIKey: BKOOMYPCSUNDGP-UHFFFAOYSA-N Copy
• CAS Registry Number: 513-35-9
• 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: Trimethylethylene; β-Isoamylene; Amylene; 1,1,2-Trimethylethylene; 2-Methyl-2-butene; 3-Methyl-2-butene; (CH3)2C=CHCH3; 2-Methylbut-2-ene; n-Amylene; Ethylene, trimethyl-; UN 2460; 2-Methylbutene-2; NSC 74118; Isopentene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Ion clustering data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • IR Spectrum
  • Gas Chromatography
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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

Reaction 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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

=

By formula: C₅H₁₀ = C₅H₁₀

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₅H₁₀ = (C₃H₉Si⁺ • C₅H₁₀)

 +  =

By formula: C₅H₁₀ + CH₄O = C₆H₁₄O

 +  =

By formula: C₅H₁₀ + HCl = C₅H₁₁Cl

 +  =

By formula: C₅H₁₀ + C₂H₆O = C₇H₁₆O

 +  =

By formula: C₅H₁₀ + C₂HF₃O₂ = C₇H₁₁F₃O₂

=

By formula: C₅H₁₀ = C₅H₁₀

=

By formula: C₅H₁₀ = C₅H₁₀

 +  =

By formula: C₅H₁₀ + Br₂ = C₅H₁₀Br₂

 +  =

By formula: H₂ + C₅H₁₀ = C₅H₁₂

 +  =

By formula: C₅H₁₀ + CH₄O = C₆H₁₄O

=  + 

By formula: C₇H₁₆O = C₅H₁₀ + C₂H₆O

Ion clustering 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: Michael M. Meot-Ner (Mautner) and Sharon G. Lias

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₅H₁₀ = (C₃H₉Si⁺ • C₅H₁₀)

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

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, Mass spectrum (electron ionization), Notes

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

Wiberg and Hao, 1991
Wiberg, K.B.; Hao, S., Enthalpies of hydration of alkenes. 4. Formation of acyclic tert-alcohols, J. Org. Chem., 1991, 56, 5108-5110. [all data]

Good and Smith, 1979
Good, W.D.; Smith, N.K., The enthalpies of combustion of the isomeric pentenes in the liquid state. A warning to combustion calorimetrists about sample drying, J. Chem. Thermodyn., 1979, 11, 111-118. [all data]

Chao, Hall, et al., 1983
Chao, J.; Hall, K.R.; Yao, J.M., Thermodynamic properties of simple alkenes, Thermochim. Acta, 1983, 64(3), 285-303. [all data]

Todd, Oliver, et al., 1947
Todd, S.S.; Oliver, G.D.; Huffman, H.M., The heat capacities, heats of fusion and entropies of the six pentenes, J. Am. Chem. Soc., 1947, 69, 1519-1525. [all data]

Parks and Huffman, 1930
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds, J. Am. Chem. Soc., 1930, 52, 4381-4391. [all data]

Rihko, Linnekoski, et al., 1994
Rihko, L.K.; Linnekoski, J.A.; Krause, A.O., Reaction equilibria in the synthesis of 2-methoxy-2-methylbutane and 2-ethyoxy-2-methylbutane in the liquid phase, J. Chem. Eng. Data, 1994, 39, 700-704. [all data]

Li and Stone, 1989
Li, X.; Stone, J.A., Determination of the beta silicon effect from a mass spectrometric study of the association of trimethylsilylium ion with alkenes, J. Am. Chem. Soc., 1989, 111, 15, 5586, https://doi.org/10.1021/ja00197a013 . [all data]

Serda, Izquierdo, et al., 1995
Serda, J.A.; Izquierdo, J.F.; Tejero, J.; Cunill, F.; Iborra, M., Equilibrium and thermodynamics for 2-methyl-2-methoxybutane liquid-phase decomposition, Thermochim. Acta, 1995, 259, 111-120. [all data]

Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J., Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions, J. Am. Chem. Soc., 1980, 102, 3329-3334. [all data]

Radyuk, Kabo, et al., 1973
Radyuk, Z.A.; Kabo, G.Ya.; Andreevskii, D.N., Isomerization equilibrium and thermodynamic properties of methylbutenes, Neftekhimiya, 1973, 13, 356-360. [all data]

Conn, Kistiakowsky, et al., 1938
Conn, J.B.; Kistiakowsky, G.B.; Smith, E.A., Heats of organic reactions. VII. Addition of halogens to olefins, J. Am. Chem. Soc., 1938, 60, 2764-2771. [all data]

Kistiakowsky, Ruhoff, et al., 1936
Kistiakowsky, G.B.; Ruhoff, J.R.; Smith, H.A.; Vaughan, W.E., Heats of organic reactions. III. Hydrogenation of some higher olefins, J. Am. Chem. Soc., 1936, 58, 137-145. [all data]

Sharonov, Rozhnov, et al., 1995
Sharonov, K.G.; Rozhnov, A.M.; Korol'kov, A.V.; Karaseva, S.Y., Enthalpies of formation of 2-methyl-2-ethoxypropane and 2-ethyl-2-ethoxypropane from equilibrium measurements, J. Chem. Thermodyn., 1995, 27, 751-753. [all data]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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