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cis-2,3-Butylene carbonate

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cis-2,3-Butylene carbonate
Names
Preferred IUPAC name (4R,5S)-4,5-Dimethyl-1,3-dioxolan-2-one
Other names cis-4,5-Dimethyl-1,3-dioxolan-2-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H8O3/c1-3-4(2)8-5(6)7-3/h3-4H,1-2H3/t3-,4+Key: LWLOKSXSAUHTJO-ZXZARUISSA-N
  • InChI=1/C5H8O3/c1-3-4(2)8-5(6)7-3/h3-4H,1-2H3/t3-,4+Key: LWLOKSXSAUHTJO-ZXZARUISBW
SMILES
  • O=C1O(C)(O1)C
  • O=C1O(C)(C)O1
Properties
Chemical formula C5H8O3
Molar mass 116.116 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

cis-2,3-Butylene carbonate is an organic compound with formula C
5H
8O
3, 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 a 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.

See also

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
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