2,3-Epoxybutane

2,3-Epoxybutane
Names
	IUPAC name 2,3-Dimethyloxirane
	Other names 1,2-Butyleneoxide, 1,2-Buteneoxide
Identifiers
CAS Number	3266-23-7; meso or cis: 1758-33-4; S,S: 21490-63-1; R,R: 1758-32-3;
3D model (JSmol)	Interactive image; meso or cis: Interactive image; S,S: Interactive image; R,R: Interactive image;
ECHA InfoCard	100.019.889
EC Number	221-877-8; meso or cis: 244-406-8; R,R: 244-406-8;
PubChem CID	18632; meso or cis: 92162; S,S: 30664; R,R: 6432237;
UN number	3271
CompTox Dashboard (EPA)	DTXSID5025239 ;
	InChI 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;
	SMILES 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
Chemical formula	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).
	Infobox references

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

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]

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References

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
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: 7139–7140. doi:10.1021/JA981031L.

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[Ullmann-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: 7139–7140. doi:10.1021/JA981031L.