(2R,3R)-2,3-bis(4-methylbenzoyloxy)butanedioic acid

• ChemBase ID: 77482
• Molecular Formular: C20H18O8
• Molecular Mass: 386.35212
• Monoisotopic Mass: 386.10016754
• SMILES: O([C@H]([C@@H](OC(=O)c1ccc(cc1)C)C(=O)O)C(=O)O)C(=O)c1ccc(cc1)C
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)OC(=O)c1ccc(cc1)C)OC(=O)c1ccc(cc1)C
• InChI: InChI=1S/C20H18O8/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14/h3-10,15-16H,1-2H3,(H,21,22)(H,23,24)/t15-,16-/m1/s1
• InChIKey: CMIBUZBMZCBCAT-HZPDHXFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-bis(4-methylbenzoyloxy)butanedioic acid
• IUPAC Traditional name: (2R,3R)-2,3-bis(4-methylbenzoyloxy)butanedioic acid
• Synonyms: (-)-O,O'-Di-p-toluoyl-L-tartaric acid; (2R,3R)-2,3-Bis[(4-methylbenzoyl)oxy]succinic acid; Di-p-toluyl-L-tartaric acid; (-)-O,O′-Di-p-toluoyl-L-tartaric acid; (2R,3R)-2,3-Bis((4-methylbenzoyl)oxy)succinic acid; Di-p-toluoyl-D-tartaric acid; Di-p-toluoyl-L-tartaric acid; 二对甲苯酰基-L-酒石酸; (-)-O,O′-二对甲苯酰基-L-酒石酸; 二对甲苯酰基-D-酒石酸; 二对甲苯酰基-L-酒石酸

Database IDs

• CAS Number: 32634-66-5; 32634-68-7
• EC Number: 251-131-7; 251-132-2
• MDL Number: MFCD00008552; MFCD00064440
• Beilstein Number: 2022481; 3225584
• PubChem SID: 162042354; 24867435; 24863105
• PubChem CID: 3037000

CALCULATED PROPERTIES

• Acid pKa: 2.8210018
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.7829022
• LogD (pH = 7.4): -1.8656341
• Log P: 4.1886425
• Molar Refractivity: 95.9398 cm^3
• Polarizability: 37.12853 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 166-171°C; 169-171 °C(lit.); 169-171°C; 169-171°C
• Optical Rotation: [α]20/D -138°, c = 1 in ethanol; [α]20/D -139±2°, c = 1% in ethanol; +139 (c=1 in ethanol); -139 (c=1 in ethanol)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); 97%; 98%
• Grade: purum
• Linear Formula: [CH3C6H4CO2CH(CO2H)-]2
• Empirical Formula (Hill Notation): C20H18O8

DETAILS

Sigma Aldrich - 371416

Application
Resolving agent for racemic amines.1,2
Packaging
25 g in poly bottle
5 g in glass bottle

REFERENCES

• Resolving agent for chiral bases.