(2R)-2-phenylbutanedioic acid

• ChemBase ID: 152765
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: c1ccc(cc1)[C@@H](CC(=O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](c1ccccc1)CC(=O)O
• InChI: InChI=1S/C10H10O4/c11-9(12)6-8(10(13)14)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)(H,13,14)/t8-/m1/s1
• InChIKey: LVFFZQQWIZURIO-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-phenylbutanedioic acid
• IUPAC Traditional name: (2R)-2-phenylbutanedioic acid
• Synonyms: (R)-(-)-Phenylsuccinic acid; (R)-(-)-苯基丁二酸

Database IDs

• CAS Number: 46292-93-7
• MDL Number: MFCD00065930
• Beilstein Number: 3201702
• PubChem SID: 162246908; 24887267
• PubChem CID: 736145

CALCULATED PROPERTIES

• Acid pKa: 4.068308
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.38282058
• LogD (pH = 7.4): -3.573225
• Log P: 1.2783073
• Molar Refractivity: 48.2065 cm^3
• Polarizability: 18.776299 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 173-176 °C
• Optical Rotation: [α]20/D -175±4°, c = 1% in acetone

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥96.0% (sum of enantiomers, HPLC)
• Empirical Formula (Hill Notation): C10H10O4

DETAILS

Sigma Aldrich - 78172

Other Notes
Chiral building block; preparation of 3-phenylpyrrolidine1; reduction to 2-phenyl-1,4-butanediol and synthesis of the dibromide2; preparation of 3-oxo-1-indanecarboxylic acid3
Packaging
1 g in glass bottle