(S)-2-methoxy-2-phenylacetic acid, CAS No. 26164-26-1

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26164-26-1

Catalog No. EBD2204021

CAS 26164-26-1

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

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Basic Information

Synonyms: S-(+)-α-MPA (S)-2-methoxy-2-phenylaceticacid (S)-(-)-α-methoxyphenylaceticacid (2S)-Methoxy(phenyl)acetate benzeneaceticacid,alpha-methoxy-,ion(1-),(alphaS)- (2S)-methoxy(phenyl)ethanoate (S)-α-Methoxybenzeneaceticacid (S)-(+)-Alpha-MethoxyphenylaceticAcid o-methyl-l-mandelicacid -methoxyphenylaceticacid o-methyl-(s)-mandelicacid -methoxybenzeneaceticacid methoxy(phenyl)aceticacid (s)-(+)-methoxyphenylaceticacid (2s)-2-methoxy-2-phenylaceticacid (s)-(+)-a-methoxyphenylaceticacid

Molecular Formula: C9H10O3

Molecular Weight: 166.17

MDL Number: MFCD00064216

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Carboxylic Acids and Esters

Product Description:

(S)-(+)-α-Methoxyphenylacetic acid is a chiral carboxylic acid derivative characterized by a methoxy group adjacent to the stereogenic center on the phenylacetic acid backbone. It is a white to off-white crystalline powder and serves as a versatile chiral building block. This compound is primarily employed as a key chiral intermediate in the pharmaceutical industry. Its main application lies in the synthesis of enantiomerically pure active pharmaceutical ingredients (APIs), particularly in the production of β-lactam antibiotics such as penicillins and cephalosporins. The (S)-configuration of the α-methoxy group is crucial for imparting the desired stereochemistry to the final drug molecule, influencing its biological activity and efficacy. Beyond its role as a pharmaceutical intermediate, it is also utilized as a chiral derivatizing agent for the resolution of racemic mixtures of amines and alcohols via diastereomeric salt formation or esterification in analytical chemistry. It is considered a valuable reagent in asymmetric synthesis for constructing complex chiral molecules.

Physical Properties

Melting Point: 64-66 °C(lit.)

Boiling Point: 164-166°C 18mm

Flash Point: 164-166°C/18mm

Density: 1.183 g/cm3

Solubility: soluble in water

Refractivity: 147 ° (C=0.5, EtOH)

Analytical Data

Appearance: White Solid