(S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid
Synonym(s):(−)-MTPA;Mosher’s acid
- CAS NO.：17257-71-5
- Empirical Formula: C10H9F3O3
- Molecular Weight: 234.17
- MDL number: MFCD00064200
- EINECS: 241-292-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-04-23 13:52:06
What is (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid?
Chemical properties
clear colorless viscous liquid
The Uses of (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid
(S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid is used as a chiral derivatizing agent, it reacts with an alcohol or amine of unknown stereochemistry to form an ester or amide. The absolute configuration of the ester or amide is then determined by proton and/or 19F NMR spectroscopy.
General Description
(S)-(-)-α-Methoxy-α-(trifluoromethyl)phenylacetic acid is commonly used as a derivatizing agent in Mosher ester analysis and Mosher amide analysis, which are NMR-based methods for determining the absolute configuration of the chiral carbon center in secondary alcohols and amines, respectively.
Purification Methods
A likely impurity is phenylethylamine from the resolution. Dissolve the acid in Et2O/*benzene (3:1), wash with 0.5N H2SO4, then water, dry over magnesium sulfate, filter, evaporate and distil it. [Dale et al. J Org Chem 34 2543 1969, J Am Chem Soc 75 512 1973.]
Properties of (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid
| Melting point: | 46-49 °C(lit.) |
| Boiling point: | 95-97 °C0.05 mm Hg(lit.) |
| alpha | D24 -71.8± 0.6° (c = 3.28 in CH3OH) |
| Density | 1.303 g/mL at 25 °C(lit.) |
| refractive index | n |
| Flash point: | >230 °F |
| storage temp. | 2-8°C |
| solubility | Readily soluble in hexane, ether, THF, CH2Cl2, benzene. |
| form | Viscous Liquid or Low Melting Solid |
| pka | 1.47±0.10(Predicted) |
| Specific Gravity | 1.303 |
| color | Clear colorless or white |
| optical activity | [α]20/D 73±1°, c = 2% in methanol |
| Sensitive | Hygroscopic |
| Merck | 14,6280 |
| BRN | 3591561 |
| CAS DataBase Reference | 17257-71-5(CAS DataBase Reference) |
Safety information for (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid
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