(2R)-2-(acetyloxy)-2-phenylacetic acid

• ChemBase ID: 148983
• Molecular Formular: C10H10O4
• Molecular Mass: 194.184
• Monoisotopic Mass: 194.0579088
• SMILES: CC(=O)O[C@H](c1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](c1ccccc1)OC(=O)C
• InChI: InChI=1S/C10H10O4/c1-7(11)14-9(10(12)13)8-5-3-2-4-6-8/h2-6,9H,1H3,(H,12,13)/t9-/m1/s1
• InChIKey: OBCUSTCTKLTMBX-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-(acetyloxy)-2-phenylacetic acid
• IUPAC Traditional name: (R)-(acetyloxy)(phenyl)acetic acid
• Synonyms: (R)-(-)-α-Acetoxyphenylacetic acid; (-)-O-Acetyl-D-mandelic acid; (R)-(-)-O-Acetylmandelic acid; (R)-2-Acetoxy-2-phenylacetic acid; (-)-O-乙酰基-D-扁桃酸; (R)-(-)-α-乙酰氧基苯乙酸

Database IDs

• CAS Number: 51019-43-3
• MDL Number: MFCD00004249
• Beilstein Number: 2694110
• PubChem SID: 24855256; 162243153
• PubChem CID: 2733814

CALCULATED PROPERTIES

• Acid pKa: 3.6172729
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.5417314
• LogD (pH = 7.4): -1.9999727
• Log P: 1.336961
• Molar Refractivity: 47.8553 cm^3
• Polarizability: 19.013554 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 97-99 °C(lit.); 98-101 °C
• Optical Rotation: [α]20/D -152.4°, c = 2 in acetone; [α]20/D -155±3°, c = 2% in acetone

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); 95+%; 98%; 99%
• Grade: purum
• Optical Purity: ee: 98% (GLC)
• Linear Formula: CH3CO2CH(C6H5)CO2H

DETAILS

Sigma Aldrich - 253030

Packaging
5 g in glass bottle
Application
The (R)- and (S)-isomers are chiral derivatizing agents for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines.1

Sigma Aldrich - 00875

Other Notes
Chiral auxiliary used for determining the enantiomeric purity and for the resolution of alcohols1,2; Review 3