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| | (-)-DIPIVALOYL-L-TARTARIC ACID Basic information |
| Product Name: | (-)-DIPIVALOYL-L-TARTARIC ACID | | Synonyms: | (-)-BIS(2,2-DIMETHYLPROPIONYL)-L-TARTARIC ACID;(-)-DIPIVALOYL-L-TARTARIC ACID;DIPIVALOYL-L-TARTARIC ACID;O,O`-Dipivaloyl-L-tartaric acid;DIPIVALOYL-L-TARTARIC ACID 98%;(-)-O,O'-Dipivaloyl-L-tartaric acid, 98+%;Butanedioic acid,2,3-bis(2,2-diMethyl-1-oxopropoxy)-, (2R,3R)-;(2R,3R)-2,3-Bis(2,2-dimethyl-1-oxopropoxy)butanedioic acid | | CAS: | 65259-81-6 | | MF: | C14H22O8 | | MW: | 318.32 | | EINECS: | 202-303-5 | | Product Categories: | chiral;Asymmetric Synthesis;Synthetic Organic Chemistry | | Mol File: | 65259-81-6.mol |  |
| | (-)-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 Rotation | [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 Statements | 22-24/25 | | WGK Germany | 3 | | HS Code | 29189900 | | Storage Class | 11 - Combustible Solids |
| | (-)-DIPIVALOYL-L-TARTARIC ACID Usage And Synthesis |
| Description | (-)-Dipivaloyl-l-tartaric acid is mainly used as a chiral resolving agent to resolve racemic compounds such as amines, and can also be used as a ligand/intermediate in organic 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 Preparation Products And Raw materials |
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