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(-)-Dipivaloyl-L-tartaric Acid

CAS No.
65259-81-6
Chemical Name:
(-)-Dipivaloyl-L-tartaric Acid
Synonyms
(-)-DPTA;DIPIVALOYL-L-TAR;L-Dipivaloytartaric Acid;L-Dipivaloyltartaric acid;DIPIVALOYL-L-TARTARIC ACID;(-)-DIPIVALOYL-L-TARTARIC ACID;DIPIVALOYL-L-TARTARIC ACID 98%;O,O`-Dipivaloyl-L-tartaric acid;(-)-Dipivaloyl-L-tartaricAcid>(-)-O,O'-Di-pivaloyl-L-tartaric acid
CBNumber:
CB8346067
Molecular Formula:
C14H22O8
Molecular Weight:
318.32
MDL Number:
MFCD00066535
MOL File:
65259-81-6.mol
MSDS File:
SDS
Last updated:2025-01-27 09:38:02

(-)-Dipivaloyl-L-tartaric Acid 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.
pka 1.68±0.25(Predicted)
form powder to crystal
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)
UNSPSC Code 12352108
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Safety Statements  22-24/25
WGK Germany  3
HS Code  29189900
NFPA 704
0
0 1

(-)-Dipivaloyl-L-tartaric Acid price More Price(21)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 43457 (?)-O,O′-Di-pivaloyl-L-tartaric acid ≥98.0% (T) 65259-81-6 5g $66.8 2023-06-20 Buy
TCI Chemical D2686 (-)-Dipivaloyl-L-tartaric Acid >98.0%(T) 65259-81-6 5g $64 2024-03-01 Buy
TCI Chemical D2686 (-)-Dipivaloyl-L-tartaric Acid >98.0%(T) 65259-81-6 25g $226 2024-03-01 Buy
Alfa Aesar H56032 (-)-O,O'-Dipivaloyl-L-tartaric acid, 98+% 65259-81-6 1g $20.6 2023-06-20 Buy
Alfa Aesar H56032 (-)-O,O'-Dipivaloyl-L-tartaric acid, 98+% 65259-81-6 5g $64.6 2021-12-16 Buy
Product number Packaging Price Buy
43457 5g $66.8 Buy
D2686 5g $64 Buy
D2686 25g $226 Buy
H56032 1g $20.6 Buy
H56032 5g $64.6 Buy

(-)-Dipivaloyl-L-tartaric Acid Chemical Properties,Uses,Production

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.

87-69-4
3282-30-2
65259-81-6
Synthesis of (-)-Dipivaloyl-L-tartaric Acid from L(+)-Tartaric acid and Pivaloyl chloride

(-)-Dipivaloyl-L-tartaric Acid Preparation Products And Raw materials

Raw materials

Preparation Products

Global( 139)Suppliers
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View Lastest Price from (-)-Dipivaloyl-L-tartaric Acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
(-)-DIPIVALOYL-L-TARTARIC ACID pictures 2025-04-21 (-)-DIPIVALOYL-L-TARTARIC ACID
65259-81-6
US $0.00-0.00 / g 1g 98 1000 Wuhan Circle Star Chem-medical Technology Co.,Ltd
(-)-O-ACETYL-D-MANDELIC ACID     pictures 2019-07-06 (-)-O-ACETYL-D-MANDELIC ACID
65259-81-6
US $20.00 / KG 10KG 98% 100kg Career Henan Chemical Co
Butanedioic acid,2,3-bis(2,2-diMethyl-1-oxopropoxy)-, (2R,3R)- (2R,3R)-2,3-Bis(2,2-dimethyl-1-oxopropoxy)butanedioic acid L-Dipivaloyltartaric acid (2R,3R)-2,3-Bis(pivaloyloxy)succinic acid (-)-BIS(2,2-DIMETHYLPROPIONYL)-L-TARTARIC ACID (-)-DIPIVALOYL-L-TARTARIC ACID DIPIVALOYL-L-TARTARIC ACID (-)-DPTA O,O`-Dipivaloyl-L-tartaric acid DIPIVALOYL-L-TARTARIC ACID 98% (-)-O,O'-Dipivaloyl-L-tartaric acid, 98+% DIPIVALOYL-L-TAR L-Dipivaloytartaric Acid 2-(2,2-dimethyl-1-oxopropoxy)-2-(2,2-dimethyl-1-oxopropyl)-3-hydroxybutanedioic acid (-)-Dipivaloyl-L-tartaricAcid> (-)-O,O'-Di-pivaloyl-L-tartaric acid (2R,3R)-2,3-Bis(2,2-Dimethyl-1-Oxopropoxy)-ButanedioicAci (2R,3R)-2,3-bis(2,2-dimethylpropanoyloxy)butanedioic acid (-)-di-O,O'-pivaloyl-L-tartaric acid (?)-O,O′-Di-pivaloyl-L-tartaric acid (?)-O,O′-Di-pivaloyl-L-tartaric acid 65259-81-6 Asymmetric Synthesis Organic Building Blocks Carboxylic Acids Chiral Building Blocks chiral Asymmetric Synthesis Synthetic Organic Chemistry