(2R)-2-methoxy-2-phenylacetic acid

• ChemBase ID: 130932
• Molecular Formular: C9H10O3
• Molecular Mass: 166.1739
• Monoisotopic Mass: 166.06299418
• SMILES: CO[C@H](c1ccccc1)C(=O)O
• Canonical SMILES: CO[C@H](c1ccccc1)C(=O)O
• InChI: InChI=1S/C9H10O3/c1-12-8(9(10)11)7-5-3-2-4-6-7/h2-6,8H,1H3,(H,10,11)/t8-/m1/s1
• InChIKey: DIWVBIXQCNRCFE-MRVPVSSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-methoxy-2-phenylacetic acid
• IUPAC Traditional name: (R)-methoxy(phenyl)acetic acid
• Synonyms: O-Methyl-D-mandelic acid; (R)-(-)-α-Methoxyphenylacetic acid; (2R)-2-methoxy-2-phenylacetic acid; O-甲基-D-扁桃酸; (R)-(-)-α-甲氧基苯乙酸

Database IDs

• CAS Number: 3966-32-3
• EC Number: 223-580-9
• MDL Number: MFCD00004250
• Beilstein Number: 2209198
• PubChem SID: 24854965; 162225210; 24883696; 24883692
• PubChem CID: 2724294

CALCULATED PROPERTIES

• Acid pKa: 3.86125
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.104102835
• LogD (pH = 7.4): -1.6942174
• Log P: 1.5389621
• Molar Refractivity: 43.455 cm^3
• Polarizability: 17.063671 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 64-67 °C; 66 - 68°C; 66-68 °C(lit.)
• Optical Rotation: [α]20/D -146°, c = 0.5 in ethanol; [α]20/D -147±3°, c = 0.5% in ethanol; [α]20/D -149±2°, c = 0.5% in ethanol
• Hydrophobicity(logP): 1.364

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); ≥99.0%; ≥99.0% (T); 95%; 99%
• Grade: for chiral derivatization; purum
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Linear Formula: C6H5CH(OCH3)CO2H

DETAILS

Sigma Aldrich - 248967

Packaging
1 g in glass bottle

Sigma Aldrich - 65212

Other Notes
Reagent used for the resolution of alcohols and the determination of enantiomeric purity1,2,3,4

Sigma Aldrich - 65209

Other Notes
Chiral reagent for the det. of enantiomeric purity and absolute configuration of sec-alcohols and α-chiral amines by NMR1,2; Analysis of amines using the ONSu ester3,4