2,3-Epoxybutane

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2,3-Epoxybutane
Meso-2,3-epoxybutane.png
2,3-expoxybutane,chiral.png
Names
Preferred IUPAC name
2,3-Dimethyloxirane
Other names
2,3-Butyleneoxide, 2,3-Buteneoxide
Identifiers
3D model (JSmol)
ECHA InfoCard 100.019.889 Edit this at Wikidata
EC Number
  • 221-877-8
  • meso or cis: 244-406-8
  • R,R: 244-406-8
UN number 3271
  • InChI=1S/C4H8O/c1-3-4(2)5-3/h3-4H,1-2H3
    Key: PQXKWPLDPFFDJP-UHFFFAOYSA-N
  • meso or cis: InChI=1S/C4H8O/c1-3-4(2)5-3/h3-4H,1-2H3/t3-,4+
    Key: PQXKWPLDPFFDJP-ZXZARUISSA-N
  • S,S: InChI=1S/C4H8O/c1-3-4(2)5-3/h3-4H,1-2H3/t3-,4-/m0/s1
    Key: PQXKWPLDPFFDJP-IMJSIDKUSA-N
  • R,R: InChI=1S/C4H8O/c1-3-4(2)5-3/h3-4H,1-2H3/t3-,4-/m1/s1
    Key: PQXKWPLDPFFDJP-QWWZWVQMSA-N
  • CC1C(O1)C
  • meso or cis: C[C@@H]1[C@@H](O1)C
  • S,S: C[C@H]1[C@@H](O1)C
  • R,R: C[C@@H]1[C@H](O1)C
Properties
C4H8O
Molar mass 72.107 g·mol−1
Appearance colorless liquid
Density 0.837 g·cm−3
Boiling point 64–78 °C (147–172 °F; 337–351 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2,3-Epoxybutane is an organic compound with the formula CH3CH(O)CHCH3. It is an epoxide. The compound exists as three stereoisomers, a pair of enantiomers and the meso isomer. All are colorless liquids.

Preparation and reactions[edit]

2,3-Epoxybutane is prepared from 2-butene via the chlorohydrin:[1]

CH3CH=CHCH3 + HOCl → CH3CH(OH)CH(Cl)CH3
CH3CH(OH)CH(Cl)CH3 → CH3CH(O)CHCH3 + HCl

A common reaction is its hydration to 2,3-butanediol. Many such ring-opening reactions have been reported.[2]

References[edit]

  1. ^ Heinz Gräfje, Wolfgang Körnig, Hans-Martin Weitz, Wolfgang Reiß, Guido Steffan, Herbert Diehl, Horst Bosche, Kurt Schneider and Heinz Kieczka "Butanediols, Butenediol, and Butynediol" in Ullmann's Encyclopedia of Industrial Chemistry, 2019, Wiley-VCH, Weinheim. doi:10.1002/14356007.a04_455.pub2
  2. ^ Nugent, William A. (1998). "Desymmetrization of Meso Epoxides with Halides: A New Catalytic Reaction Based on Mechanistic Insight". Journal of the American Chemical Society. 120 (28): 7139–7140. doi:10.1021/JA981031L.