(-)-Dipivaloyl-L-tartaric Acid Chemical Properties

Melting point:

127-132 °C

Boiling point:

436.6±45.0 °C(Predicted)

Density 

1.240±0.06 g/cm3(Predicted)

refractive index 

-24 ° (C=2, Dioxane)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

sol Et2O, THF, aq NaHCO3 solution; insol cold H2O.

form 

powder to crystal

pka

1.68±0.25(Predicted)

color 

White to Almost white

optical activity

[α]20/D 23.5±1°, c = 1.7% in dioxane

Sensitive 

Hygroscopic

BRN 

2008171

InChI

InChI=1S/C14H22O8/c1-13(2,3)11(19)21-7(9(15)16)8(10(17)18)22-12(20)14(4,5)6/h7-8H,1-6H3,(H,15,16)(H,17,18)/t7-,8-/m1/s1

InChIKey

UFHJEZDFEHUYCR-HTQZYQBOSA-N

SMILES

C(O)(=O)[C@H](OC(=O)C(C)(C)C)[C@@H](OC(=O)C(C)(C)C)C(O)=O

CAS DataBase Reference

65259-81-6(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29189900

MSDS

• Language:English Provider:SigmaAldrich

(-)-Dipivaloyl-L-tartaric Acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(?)-O,O′-Di-pivaloyl-L-tartaric acid can be used:

• As a chiral staple in the synthesis of helical π-conjugated cyclic nanocoils, which are used as nano springs, nano solenoids, and pressure sensors.
• As an additive in the iridium-catalyzed C-H amidation reactions of arylphosphoryl compounds.

Application

(2R,3R)-Dipivaloyltartaric Acid is used as a chiral auxiliary for enantioselective protonation (deracemization) and asymmetric transformation; starting material for synthesis of chiral succinimides and polyhydroxy compounds.

Preparation

Preparative Method of (2R,3R)-Dipivaloyltartaric Acid: hydrolysis of the corresponding anhydride obtained by heating (2R,3R)-tartaric acid and pivaloyl chloride at 120-140 °C for 4 h.^[1] Drying: over P2O5 in vacuo, controlled by 1H NMR and optical rotations.

storage

(2R,3R)-Dipivaloyltartaric Acid anhydrous solid can be stored at rt in the absence of moisture. It is retrievable from its basic solution (10 % aq NaHCO3), after acidification (HCl), with a quantitative yield.2 On heating it transforms into an anhydride with elimination of one molecule of water.

References

1. Duhamel, L.; Plaquevent, J. C. OPP 1982, 14, 347.

(-)-Dipivaloyl-L-tartaric Acid(65259-81-6)Related Product Information

• DIPIVALOYL-D-TARTARIC ACID,(+)-DIPIVALOYL-D-TARTARIC ACID,O,O`-Dipivaloyl-D-tartaric acid ,DIPIVALOYL-D-TARTARIC ACID 98%
• (+)-DIPIVALOYL-D-TARTARIC ACID,DIPIVALOYL-D-TARTARIC ACID
• 2-ISOBUTOXYACETIC ACID
• ISOBUTYRIC ACID 2-ETHOXYETHYL ESTER
• (-)-DIACETYL-L-TARTARIC ACID
• (-)-DIPIVALOYL-L-TARTARIC ACID