(2S)-2-methoxy-2-phenylacetic acid

• ChemBase ID: 137681
• 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-/m0/s1
• InChIKey: DIWVBIXQCNRCFE-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-methoxy-2-phenylacetic acid
• IUPAC Traditional name: (S)-methoxy(phenyl)acetic acid
• Synonyms: O-Methyl-L-mandelic acid; (S)-(+)-α-Methoxyphenylacetic acid; O-Methyl-(R)-mandelic acid; (R)-(-)-alpha-Methoxyphenylacetic acid; O-Methyl-(S)-mandelic acid; (S)-(+)-alpha-Methoxyphenylacetic acid; L-α-Methoxyphenylacetic Acid; (S)-2-Methoxy-2-(phenyl)ethanoic Acid; (S)-(+)-O-Methylmandelic Acid; α-Methoxy-benzeneacetic Acid; (S)-(+)-α-Methoxyphenylacetic Acid; O-甲基-L-扁桃酸; (S)-(+)-α-甲氧基苯乙酸; (R)-(-)-α-甲氧基苯乙酸

Database IDs

• CAS Number: 26164-26-1; 3966-32-3
• EC Number: 223-580-9; 247-492-5
• MDL Number: MFCD00004250; MFCD00064216
• Beilstein Number: 2361718; 3589257
• PubChem SID: 24883690; 162231943; 24854969
• PubChem CID: 643325

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

• Solubility: Dichloromethane; Ether; Ethyl Acetate; Water
• Apperance: White Solid
• Melting Point: 58-60°C; 63-68°C; 64-66 °C(lit.); 64-67 °C
• Boiling Point: 164-166°C/18mm
• Optical Rotation: [α]17/D +150°, c = 1 in ethanol; [α]20/D +148°, c = 0.5 in ethanol; [α]20/D +149±2°, c = 0.5% in ethanol; +146 (c=0.5 in ethanol); -146 (c=0.5 in ethanol)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99%; ≥99.0%; ≥99.0% (T); 99%
• Grade: Flukabrand™ ChiraSelect reagent; for chiral derivatization
• Optical Purity: ee: ≥99% (GLC); enantiomeric ratio: ≥99.5:0.5 (HPLC)
• Linear Formula: C6H5CH(OCH3)CO2H

DETAILS

Sigma Aldrich - 248983

Packaging
1 g in glass bottle
Application
Reactant involved in the synthesis of biologically active molecules including:
• Acyclonucleoside phosphonates structural analogs of adefovir1
• Labeled discodermolide for studying binding to tubulin2
• 10-Isocyano-4-cadinene used for antifouling activity3Reactant involved in studies of immunostimulating chromanones gonytolides A-C4Reactant involved in:
• Hydroxylations and epoxidations5
• Hydrogenations6

Sigma Aldrich - 421766

Application
Reactant involved in the synthesis of biologically active molecules including:
• Acyclonucleoside phosphonates structural analogs of adefovir1
• Labeled discodermolide for studying binding to tubulin2
• 10-Isocyano-4-cadinene used for antifouling activity3Reactant involved in studies of immunostimulating chromanones gonytolides A-C4Reactant involved in:
• Hydroxylations and epoxidations5
• Hydrogenations6
Legal Information
Flukabrand is a trademark of Sigma-Aldrich GmbH

Sigma Aldrich - 65208

Application
Reactant involved in the synthesis of biologically active molecules including:
• Acyclonucleoside phosphonates structural analogs of adefovir1
• Labeled discodermolide for studying binding to tubulin2
• 10-Isocyano-4-cadinene used for antifouling activity3Reactant involved in studies of immunostimulating chromanones gonytolides A-C4Reactant involved in:
• Hydroxylations and epoxidations5
• Hydrogenations6

REFERENCES

• With chiral amines, forms diastereomeric amides which have been used to establish absolute configuration by ¹ H NMR: J. Org. Chem., 59, 4202 (1994); 60, 1538 (1995).
• Chiral derivatization agent for determination of absolute configuration of alcohols by NMR: Topics Stereochem ., 2, 199 (1967); J. Org. Chem., 51, 2370 (1986). Also used in determination of the absolute stereochemistry of chiral amines: J. Org. Chem., 60, 1538 (1995).