2-Butyne

2-Butyne (dimethylacetylene, crotonylene or but-2-yne) is an alkyne with chemical formula CH3C≡CCH3. Produced artificially, it is a colorless, volatile, pungent liquid at standard temperature and pressure.

2-Butyne[1][2]
Ball-and-stick model
Names
Preferred IUPAC name
But-2-yne
Other names
Dimethylacetylene
Crotonylene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.239
UNII
  • InChI=1S/C4H6/c1-3-4-2/h1-2H3 checkY
    Key: XNMQEEKYCVKGBD-UHFFFAOYSA-N checkY
  • InChI=1/C4H6/c1-3-4-2/h1-2H3
    Key: XNMQEEKYCVKGBD-UHFFFAOYAO
  • C(#CC)C
Properties
C4H6
Molar mass 54.0904 g/mol
Density 0.691 g/mL
Melting point −32 °C (−26 °F; 241 K)
Boiling point 27 °C (81 °F; 300 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

2-Butyne is of interest to physical chemists because of its very low torsional barrier and the problem of determining that barrier using high-resolution infrared spectroscopy. Analysis of its spectrum[3] leads to a determination that the torsional barrier is only 6 cm−1 (1.2×10−22 J or 72 J mol−1). However, it has not been determined whether the equilibrium structure is eclipsed (D3h) or staggered (D3d). Symmetry analysis using the Molecular Symmetry Group[4][5] G36 shows that one would need to analyse its high resolution rotation-vibration Raman spectrum to determine its equilibrium structure.

2-Butyne (dimethylethyne) forms with 5-decyne (dibutylethyne), 4-octyne (dipropylethyne) and 3-hexyne (diethylethyne) a group of symmetric alkynes.

Synthesis

2-Butyne can be synthesized by the rearrangement reaction of ethylacetylene in a solution of ethanolic potassium hydroxide.[6]

Applications

2-Butyne, along with propyne, is used to synthesize alkylated hydroquinones in the total synthesis of Vitamin E.[7]

See also

References
  1. at Sigma-Aldrich
  2. NIST Chemistry WebBook page for 2-butyne
  3. di Lauro, C.; et al. (1997). "The rotation-torsion structure in the ν11/ν15 (Gs) methyl rocking fundamental band in dimethylacetylene". J. Mol. Spectrosc. 184 (1): 177–185. doi:10.1006/jmsp.1997.7321.
  4. Longuet-Higgins, H.C. (1963). "The symmetry groups of non-rigid molecules". Molecular Physics. 6 (5): 445–460. Bibcode:1963MolPh...6..445L. doi:10.1080/00268976300100501.
  5. P. R. Bunker (1964). "The Rotation-Torsion Wavefunctions of Molecules that have two Identical Rotors". Mol. Phys. 8: 81. doi:10.1080/00268976400100091.
  6. Victor von Richter; Hans Meerwein (1916). Organic Chemistry: Chemistry of the aliphatic series Vol. I: Smith's 3rd American Ed. Philadelphia: P. Blakiston's Sons & Co. p. 89.
  7. Reppe, Walter; Kutepow, N; Magin, A (1969). "Cyclization of Acetylenic Compounds". Angewandte Chemie International Edition in English. 8 (10): 727–733. doi:10.1002/anie.196907271.


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