Diethyl tartrate

Diethyl tartrate

Names
Preferred IUPAC name Diethyl 2,3-dihydroxybutanedioate
Other names Diethyl 2,3-dihydroxysuccinate
Identifiers
CAS Number	87-91-2 Y
3D model (Jmol)	Interactive image
ChemSpider	104927 Y
ECHA InfoCard	100.001.622
PubChem	62333
InChI InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m0/s1 Y Key: YSAVZVORKRDODB-WDSKDSINSA-N Y InChI=1/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m0/s1 Key: YSAVZVORKRDODB-WDSKDSINBN
SMILES O=C(OCC)[C@@H](O)[C@H](O)C(=O)OCC
Properties
Chemical formula	C8H14O6
Molar mass	206.19 g·mol−1
Appearance	colourless
Density	1.204 g/mL
Boiling point	280 °C (536 °F; 553 K)
Solubility in water	low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diethyl tartrate is an organic compound, the ethyl ester of tartaric acid. It exists in both as a chiral isomer, showing both left- and right-handed forms, as well as a meso stereoisomer, which is not chiral. The chiral isomer is far more common.

In the Sharpless epoxidation, diethyl tartrate and titanium isopropoxide form a chiral catalyst in situ.^[1]

References

1. ↑ J. Gordon Hill, K. Barry Sharpless, Christopher M. Exon, and Ronald Regenye (1985). "Enantioselective Epoxidation of Allylic Alcohols: (2S,3S)-3-Propyloxiranemethanol". Org. Synth. 63: 66.  CS1 maint: Multiple names: authors list (link); Coll. Vol., 7, p. 461