Diisopropyl tartrate

Diisopropyl tartrate (DIPT) is a diester of tartaric acid. It has a two chiral carbon atoms giving rise to three stereoisomeric variants. It is commonly used in asymmetric synthesis as a catalyst and as chiral building block for pharmaceuticals and agrochemicals. Its main application is in Sharpless epoxidation, where it serves as a chiral ligand to titanium after reaction with titanium isopropoxide.[1]

Diisopropyl tartrate
Names
IUPAC name
Di(propan-2-yl) 2,3-dihydroxybutanedioate
Other names
Diisopropyl 2,3-dihydroxysuccinate
Diisopropyl tartrate
Bis(1-methylethyl) ester of 2,3-dihydroxybutanedioic acid
DIPT
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.009
EC Number
  • 218-709-0
UNII
  • InChI=1S/C10H18O6/c1-5(2)15-9(13)7(11)8(12)10(14)16-6(3)4/h5-8,11-12H,1-4H3/t7-,8-/m0/s1 ☒N
    Key: XEBCWEDRGPSHQH-YUMQZZPRSA-N ☒N
  • (−)-isomer: CC(C)OC(=O)C(C(C(=O)OC(C)C)O)O
  • O=C(OC(C)C)[C@@H](O)[C@H](O)C(=O)OC(C)C
Properties
C10H18O6
Molar mass 234.25 g/mol
Density 1.117 g/mL
Boiling point 152 °C (306 °F; 425 K) at 16 kPa
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

References
  1. Katsuki, Tsutomu; Sharpless, K. Barry (1980). "The first practical method for asymmetric epoxidation". J. Am. Chem. Soc. 102 (18): 5974. doi:10.1021/ja00538a077.


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