| Identification | More | [Name]
(-)-DIPIVALOYL-L-TARTARIC ACID | [CAS]
65259-81-6 | [Synonyms]
(-)-BIS(2,2-DIMETHYLPROPIONYL)-L-TARTARIC ACID
(-)-DI-O,O'-PIVALOYL-L-TARTARIC ACID
(-)-DIPIVALOYL-L-TARTARIC ACID
DIPIVALOYL-L-TARTARIC ACID
(-)-DPTA
O,O`-Dipivaloyl-L-tartaric acid
DIPIVALOYL-L-TARTARIC ACID 98% | [Molecular Formula]
C14H22O8 | [MDL Number]
MFCD00066535 | [Molecular Weight]
318.32 | [MOL File]
65259-81-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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 Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29189900 |
| Hazard Information | Back Directory | [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. |
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