S-(-)-2-phenyl-2-methoxy-2-(trifluoromethyl)acetic acid, CAS No. 17257-71-5

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17257-71-5

Catalog No. EBD20118

CAS 17257-71-5

Name S-(-)-2-phenyl-2-methoxy-2-(trifluoromethyl)acetic acid

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Basic Information

Synonyms: (S)-(-)-A-methoxy-A-(trifluoromethyl)phenylaceticacid (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylaceticacid minus-A-methoxy-A-trifluoro-methyl*phenylaceticA (-)-Moshersacid~(-)-MTPA (-)MTPA (-)-Moshersacid (S)-(-)-Mosher莝acid 3,3,3-trifluoro-2-methoxy-2-phenylpropanoicacid (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoicacid (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoicacid (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate (S)-PhC(OMe)(CF3)CO2H S-(-)-2-phenyl-2-methoxy-2-(trifluoromethyl)aceticacid

Molecular Formula: C10H9F3O3

Molecular Weight: 234.17

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Chiral Intermediates Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

(S)-(-)-α-Methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA), CAS 17257-71-5, is a chiral carboxylic acid widely recognized as Mosher's acid. Its structure features a stereogenic center adjacent to a trifluoromethyl group and a methoxy group, making it a powerful chiral derivatizing agent. The primary application of (S)-MTPA is in the field of analytical chemistry and pharmaceutical research for determining the absolute configuration and enantiomeric purity of chiral alcohols, amines, and other nucleophiles. It reacts with these compounds to form diastereomeric esters or amides (Mosher's esters/amides), which can be easily analyzed by NMR spectroscopy or chromatography. This makes it an indispensable tool in asymmetric synthesis, drug development, and the quality control of chiral pharmaceutical intermediates. Beyond its role as a derivatization reagent, (S)-MTPA and its acid chloride are also valuable as chiral auxiliaries and resolving agents in organic synthesis. Its high configurational stability and the distinct NMR signals induced by the trifluoromethyl group are key to its utility.

Physical Properties

Melting Point: 46-49 °C(lit.)

Boiling Point: 95-97 °C/0.05 mmHg(lit.)

Flash Point: 113 °C

Density: 1.303 g/mL at 25 °C(lit.)

Refractivity: n20/D 1.474(lit.)

Storage: 2-8°C