(-)-Dipivaloyl-l-tartaric acid

Basic Information

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CAS Number

65259-81-6

Molecular Formula

C14H22O8

Molecular Weight

318.32 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Esters

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

147.0 to 152.0 deg-C

Boiling Point

436.6℃ at 760 mmHg

Density

1.240±0.06 g/cm3 (20 ºC 760 Torr),

Flash Point

153.791°C

Refractive Index

-24 ° (C=2, Dioxane)

SMILES

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CC(C)(C)C(=O)OC(C(C(=O)O)OC(=O)C(C)(C)C)C(=O)O

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

LogP

1.0713999999999992

Topological Polar Surface Area

127.20000000000002 Å²

Hydrogen Bond Donor/Acceptor

2 / 8

Complexity

422

Safety Information

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Sensitiveness

Hygroscopic

Synonyms & References

English

65259-81-6
(-)-Dipivaloyl-L-tartaric Acid
(2R,3R)-2,3-bis(2,2-dimethylpropanoyloxy)butanedioic acid
SCHEMBL375902
(-)-Bis(2,2-dimethylpropionyl)-L-tartaric Acid
(-)-O,O'-Di-pivaloyl-L-tartaric acid, >=98.0% (T)
AKOS016015590
Butanedioic acid,2,3-bis(2,2-dimethyl-1-oxopropoxy)-,(2R,3R)-
dipivaloyl-L-tartaric acid
(2R,3R)-2,3-Bis(pivaloyloxy)succinicacid
C14H22O8
CS-W012016
(-)-O,O'-Di-pivaloyl-L-tartaric acid
DS-8549
F14945
MFCD00066535
D2686
(2R,3R)-2,3-Bis(pivaloyloxy)succinic acid
Butanedioic acid,2,3-bis(2,2-dimethyl-1-oxopropoxy)-, (2R,3R)-
(-)-O,O'-Dipivaloyl-L-tartaric acid
(-)-DIPIVALOYL-L-TARTARIC ACID
(?)-O,O′-Di-pivaloyl-L-tartaric acid
(2R,3R) HOOCCH(OCOtC4H9)CH(OCOtC4H9)COOH
(2R,3R)-O,O-d
(2R,3R)-O,O'-dipivaloyltartaric acid
(R)-2-amino-propionic acid methyl ester hydrochloride
(R)-alanine methyl ester hydrochloride
D-Ala methyl ester hydrochloride
D-alanine methyl ester hydrochloride
dipivaloyl-(+)-tartaric acid
H2N-D-Ala-OMe*hydrochloride

MDL Number

MFCD00451533

FAQ

What are the physical and chemical properties of (-)-Dipivaloyl-l-tartaric acid (CAS: 65259-81-6)?

(-)-Dipivaloyl-l-tartaric acid (CAS: 65259-81-6) is a crystalline compound with a molecular weight of approximately 270.3 g/mol. It has a low solubility in water but is soluble in common organic solvents like methanol and ethanol. The compound is known for its high reactivity with various nucleophiles, particularly in esterification and aldol condensation reactions.

How is (-)-Dipivaloyl-l-tartaric acid (CAS: 65259-81-6) typically synthesized?

(-)-Dipivaloyl-l-tartaric acid (CAS: 65259-81-6) is usually synthesized via the prochiral esterification of l-tartaric acid with dipivaloyl chloride. The reaction involves the use of a catalytic amount of a Lewis acid like aluminum trichloride to promote the esterification. The process yields high enantiomeric excess of the (-)-form, with a typical yield of around 85-90%.

What industries use (-)-Dipivaloyl-l-tartaric acid (CAS: 65259-81-6)?

(-)-Dipivaloyl-l-tartaric acid (CAS: 65259-81-6) is primarily used in the pharmaceutical industry for chiral synthesis, as a chiral auxiliary in the resolution of racemic mixtures. It is also utilized in the polymer industry, particularly in the synthesis of polyesters and other polymers, and in the sensor and semiconductor industries for its chiral properties.

What precautions should be taken when handling (-)-Dipivaloyl-l-tartaric acid (CAS: 65259-81-6)?

When handling (-)-Dipivaloyl-l-tartaric acid (CAS: 65259-81-6), it is essential to wear appropriate personal protective equipment (PPE), including safety glasses, gloves, and a lab coat. The compound should be handled in a well-ventilated area or a fume hood. Spills should be cleaned up immediately using appropriate absorbent materials and the area should be well-ventilated. Always refer to the Safety Data Sheet (SDS) for detailed safety information and emergency procedures.