2-Butyne

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2-Butyne[1][2]
Structural formula
Ball-and-stick model
Names
Preferred IUPAC name
But-2-yne
Other names
Dimethylacetylene
Crotonylene
Identifiers
503-17-3 YesY
ChEMBL ChEMBL119108 YesY
ChemSpider 9990 YesY
Jmol 3D model Interactive image
PubChem 10419
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 (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 (dimethylethin) forms with 5-decyne (dibutylethin), 4-octyne (dipropylethin) and 3-hexyne (diethylethin) a group of symmetric alkynes.

Synthesis[edit]

2-Butyne can be synthesized by the rearrangement of ethylacetylene in a solution of ethanolic potassium hydroxide.[3]

Applications[edit]

2-Butyne, along with propyne, is used to synthesize alkylated hydroquinones in the total synthesis of Vitamin E.[4]

See also[edit]

References[edit]

  1. ^ 2-Butyne at Sigma-Aldrich
  2. ^ NIST Chemistry WebBook page for 2-butyne
  3. ^ 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. 
  4. ^ 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. Retrieved 26 December 2013.