cis-2,3-Butylene carbonate

*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	36368-39-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	9609796 ;
PubChem CID	11434932;
UNII	5QH9AX4WRJ ;
CompTox Dashboard (EPA)	DTXSID20465672 ;
	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@@H](C)[C@H](O1)C; O=C1O[C@@H](C)[C@@H](C)O1;
Properties
Chemical formula	C5H8O3
Molar mass	116.116 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1]

References

^ 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

[matsu-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

[1]

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	36368-39-5^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	9609796^N
PubChem CID	11434932
UNII	5QH9AX4WRJ^Y
CompTox Dashboard (EPA)	DTXSID20465672
InChI InChI=1S/C5H8O3/c1-3-4(2)8-5(6)7-3/h3-4H,1-2H3/t3-,4+^N Key: LWLOKSXSAUHTJO-ZXZARUISSA-N^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@@H](C)[C@H](O1)C O=C1O[C@@H](C)[C@@H](C)O1
Properties
Chemical formula	C₅H₈O₃
Molar mass	116.116 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

cis-2,3-Butylene carbonate

See also

References