(-)-Dibenzoyl-L-tartaric acid monohydrate CAS 62708-56-9

Introduction：Basic information about (-)-Dibenzoyl-L-tartaric acid monohydrate CAS 62708-56-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

(-)-Dibenzoyl-L-tartaric acid monohydrate Basic information

• Product Name: (-)-Dibenzoyl-L-tartaric acid monohydrate
• Synonyms: L-(-)DIBENZOYL-L-TARTARIC ACID 1-HYDRATE;(2S,3S)-2,3-bis(benzoyloxy)succinic acid hydrate;O,O'-Dibenzoyl-d-Tartaric acid Anhydrous;(-)-O,O''-DIBENZOYL-L-WEINSUREMONOHYDRAT;DIBENZOYL-L-TARARIC ACID MOTOHYDRATE;(-)-Dibenzoyl-L-tartaric acid Monohydrate, 98% 100GR;(2R,3R)-(-)-DI-O-BENZOYL-TARTARIC ACID M;Dibenzoyl-L-tartaric acid Monohydrat
• CAS: 62708-56-9
• MF: C18H16O9
• MW: 376.31
• EINECS: 613-072-9
• Product Categories: chiral;Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;Widely used in chiral especially racemic amine compounds;Carboxylic Acids (Chiral);Chiral Building Blocks;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;CHIRAL CHEMICALS;Hydroxy Acids & Deriv.;Chiral Compound;Carboxylic AcidsAsymmetric Synthesis;Chiral Building Blocks;Chiral Resolution Reagents;Chiral Resolving Reagents;Organic Building Blocks
• Mol File: 62708-56-9.mol

(-)-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 Rotation: [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
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Eye Irrit. 2

(-)-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.

Synthesis

(1) take 1 portion of L-tartaric acid and appropriate amount of organic solvent into the reactor by weight, add 0.1-0.001 portion of catalyst to the reactor under stirring condition, after that, add 1~3 portions of benzoyl chloride to the reactor at a drop acceleration rate of 1-10 mL/min, and then continue the reaction for 4h after the drop is completed, and then, transfer the reaction mixture into a centrifuge for centrifugal separation. Centrifugal separation was carried out to obtain solid L-(-)-dibenzoyltartaric anhydride, standby; said catalyst was copper sulfate or ferrous sulfate;

(2) L-(-)-dibenzoyltartaric anhydride prepared in step (1) was put into the reaction kettle, to which was added an equal weight of toluene and water, and heated and refluxed at 100 ?? for 2-4h, and after that, it cooled down to the ambient temperature, and the resulting mixture was transferred to the centrifuge for the reaction, and then, the mixture was transferred to the centrifuge for the reaction, and then the reaction was continued for 4h. The mixture was transferred to a centrifuge for centrifugal separation to obtain solid L-(-)-dibenzoyltartaric acid.

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.]