cis-2,3-Butylene carbonate

cis-2,3-Butylene carbonate
IUPAC name cis-4,5-Dimethyl-[1,3]dioxolan-2-one
Identifiers
CAS number	36368-39-5
Jmol-3D images	Image 1
SMILES O=C1O[C@@H](C)[C@@H](C)O1
Properties
Molecular formula	C5H8O3
Molar mass	116.12 g mol−1
Y carbonate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

cis-2,3-Butylene carbonate is an organic compound with formula C₅H₈O₃, or (H₃C)₂(C₂H₂)(CO₃). It is an ester with a carbonate functional group bonded to both free ends of the cis-2,3-butylene group. It is also an heterocyclic compound with a five-membered ring containing two oxygen atoms, and can be viewed as a derivative of dioxolane, namely cis-4,5-dimethyl-1,3-dioxolan-2-one.

The compound is an aprotic polar solvent.

The bacterium Pseudomonas diminuta will hydrolyze this compound but not its stereoisomer trans-2,3-Butylene carbonate, yielding cis-2,3-Butanediol. This has been proposed as an efficient route to produce the latter from a racemic mixture of 2,3-butylene carbonates.^[1]

See also

• trans-2,3-Butylene carbonate, a stereoisomer
• 1,2-Butylene carbonate
• Propylene carbonate

References

1. ^ Kazutsugu Matsumoto, Youichi Sato, Megumi Shimojo and Minoru Hatanaka (2000), Highly enantioselective preparation of C2-symmetrical diols: microbial hydrolysis of cyclic carbonates. Tetrahedron: Asymmetry, volume 11, issue 9, pages 1965-1973. {{doi:10.1016/S0957-4166(00)00144-0}}