Diethyl tartrate
Appearance
Skeletal formula of diethyl tartrate | |
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Names | |
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Preferred IUPAC name
Diethyl 2,3-dihydroxybutanedioate | |
Other names
Diethyl 2,3-dihydroxysuccinate
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Identifiers | |
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3D model (JSmol)
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ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C8H14O6 | |
Molar mass | 206.194 g·mol−1 |
Appearance | Colorless liquid |
Density | 1.204 g/mL |
Boiling point | 280 °C (536 °F; 553 K) |
low | |
-113.4·10−6 cm3/mol | |
Hazards | |
Safety data sheet (SDS) | Diethyl D-Tartrate MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Diethyl tartrate is an organic compound with the formula (HOCHCO2Et)2 (Et = ethyl). Three stereoisomers exist, R,R-, S,S-, and R,S (=S,R-). They are the ethyl esters of the respective R,R-, S,S-, and R,S-tartaric acids. The R,R- and S,S- isomers are enantiomeric, being mirror images. The meso stereoisomer 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
- ^ Hill, J. Gordon; Sharpless, K. Barry; Exon, Christopher M.; Regenye, Ronald (1985). "Enantioselective Epoxidation of Allylic Alcohols: (2S,3S)-3-Propyloxiranemethanol". Organic Syntheses. 63: 66. doi:10.15227/orgsyn.063.0066.