(-)-Dibenzoyl-L-tartaric acid monohydrate Chemical Properties

Melting point:

88-89 °C(lit.)

alpha 

-115 º (c=5, ethanol)

refractive index 

-108.5 ° (C=1, EtOH)

storage temp. 

Store below +30°C.

form 

Powder

color 

White

optical activity

[α]20/D 110±3°, c = 5% in ethanol

Water Solubility 

SOLUBLE

BRN 

4065263

InChI

InChI=1/C18H14O8.H2O/c19-15(20)13(25-17(23)11-7-3-1-4-8-11)14(16(21)22)26-18(24)12-9-5-2-6-10-12;/h1-10,13-14H,(H,19,20)(H,21,22);1H2/t13-,14-;/s3

InChIKey

DXDIHODZARUBLA-DTPOWOMPSA-N

SMILES

[C@@H](C(=O)O)(OC(=O)C1C=CC=CC=1)[C@H](C(=O)O)OC(=O)C1C=CC=CC=1.O |&1:0,13,r|

CAS DataBase Reference

62708-56-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

WW8070000

F 

3

TSCA 

Yes

HS Code 

29181990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(-)-Dibenzoyl-L-tartaric acid monohydrate Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(-)-Dibenzoyl-L-tartaric acid is used as an intermediate in pharmaceutical and agro chemical industries. It is used as chiral auxiliary in organic synthesis and as a resolution agent in the synthesis of rameleton.

General Description

(-)-O,O′-Dibenzoyl-L-tartaric acid monohydrate may be used as a chiral resolving agent for the resolution of racemic bioactive compounds such as (±)-3-(3-hydroxyphenyl)-N-(1-propyl)-piperidine and (±)-2-(5,6-dimethoxy-1,2,3,4-tetrahydro-1-naphthyl)-imidazoline to isolate the corresponding (-)-enantiomeric forms.

Purification Methods

Crystallise the acid from water (18g from 400 mL boiling H2O) and stir vigorously while cooling in order to obtain crystals; otherwise an oil will separate which solidifies on cooling. Dry it in a vacuum desiccator over KOH/H2SO4 (yield 16.4g) as monohydrate, m 88-89o. It crystallises from xylene as the anhydrous acid, m 173o (150-153o). It does not crystallise from *C6H6, toluene, *C6H6/pet ether (oil), or CHCl3/pet ether. [Butler & Cretcher J Am Chem Soc 55 2605 1933, Acs et al. Tetrahedron 41 2465 1985, R(+) Beilstein 9 IV 557, S(-) Beilstein 9 III 870.]

(-)-Dibenzoyl-L-tartaric acid monohydrate(62708-56-9)Related Product Information

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