Diethyl tartrate

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
  • 408332-88-7 checkY
  • 87-91-2 (R,R)-(+)-L
  • 13811-71-7 (S,S)-(−)-D
  • 57968-71-5 (D/L)
  • 21066-72-8 meso
3D model (JSmol)
  • Interactive image
ChemSpider
  • 104927 checkY
PubChem CID
  • 62333
UNII
  • OQ72CPY58Z (R,R)-(+)-L checkY
CompTox Dashboard (EPA)
  • DTXSID70859148 Edit this at Wikidata
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 checkY
    Key: YSAVZVORKRDODB-WDSKDSINSA-N checkY
  • 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
  • O=C(OCC)[C@@H](O)[C@H](O)C(=O)OCC
Properties
Chemical formula
 C8H14O6
Molar mass 206.194 g·mol−1
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)
 -113.4·10−6 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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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.[1] The TADDOL ligand scaffold is produced from diethyl tartrate.[2]

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)