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Diethyl tartrate

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Diethyl tartrate
Skeletal formula of diethyl tartrate
Ball-and-stick model of the diethyl tartrate molecule
Names
Preferred IUPAC name Diethyl 2,3-dihydroxybutanedioate
Other names Diethyl 2,3-dihydroxysuccinate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: YSAVZVORKRDODB-WDSKDSINSA-N
  • 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/s1Key: YSAVZVORKRDODB-WDSKDSINBN
SMILES
  • O=C(OCC)(O)(O)C(=O)OCC
Properties
Chemical formula C8H14O6
Molar mass 206.194 g·mol
Appearance Colorless liquid
Density 1.204 g/mL
Melting point 17 °C (63 °F; 290 K)
Boiling point 280 °C (536 °F; 553 K)
Solubility in water low
Magnetic susceptibility (χ) -113.4·10 cm/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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. The TADDOL ligand scaffold is produced from diethyl tartrate.

References

  1. 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.
  2. Henrik Teller, Susanne Flügge, Richard Goddard, Alois Fürstner (2010). "Enantioselective Gold Catalysis: Opportunities Provided by Monodentate Phosphoramidite Ligands with an Acyclic TADDOL Backbone". Angew. Chem. Int. Ed. 49 (11): 1949–1953. doi:10.1002/anie.200906550. PMID 20175172.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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