2,3-Epoxybutane

Source: Wikipedia, the free encyclopedia.
2,3-Epoxybutane
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

meso isomer
. All are colorless liquids.

Preparation and reactions

2,3-Epoxybutane is prepared from

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

ring-opening reactions have been reported.[2]

References