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Mosher's acid

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Mosher's acid
Names
IUPAC names (R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid
(S)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoic acid
Other names Methoxy(trifluoromethyl)phenylacetic acid, MTPA
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.153.604 Edit this at Wikidata
EC Number
  • (R): 243-829-5
  • (S): 241-292-1
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H9F3O3/c1-16-9(8(14)15,10(11,12)13)7-5-3-2-4-6-7/h2-6H,1H3,(H,14,15)Key: JJYKJUXBWFATTE-UHFFFAOYSA-N
  • InChI=1/C10H9F3O3/c1-16-9(8(14)15,10(11,12)13)7-5-3-2-4-6-7/h2-6H,1H3,(H,14,15)Key: JJYKJUXBWFATTE-UHFFFAOYAJ
SMILES
  • COC(C(O)=O)(c1ccccc1)C(F)(F)F
Properties
Chemical formula C10H9F3O3
Molar mass 234.17
Appearance solid
Melting point 46 to 49 °C (115 to 120 °F; 319 to 322 K)
Boiling point 105 to 107 °C (221 to 225 °F; 378 to 380 K) at 1 torr
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Flash point 110 °C (230 °F; 383 K)
Related compounds
Related acyl chloride Mosher's acid chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Mosher's acid, or α-methoxy-α-trifluoromethylphenylacetic acid (MTPA) is a carboxylic acid which was first used by Harry Stone Mosher as a chiral derivatizing agent. It is a chiral molecule, consisting of R and S enantiomers.

Applications

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 F NMR spectroscopy.

Mosher's acid chloride, the acid chloride form, is sometimes used because it has better reactivity.

See also

References

  1. J. A. Dale; D. L. Dull; H. S. Mosher (1969). "α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines". Journal of Organic Chemistry. 34 (9): 2543–2549. doi:10.1021/jo01261a013.
  2. J. A. Dale; H. S. Mosher (1973). "Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters". Journal of the American Chemical Society. 95 (2): 512–519. doi:10.1021/ja00783a034.
  3. Y. Goldberg; H. Alper (1992). "A new and simple synthesis of Mosher's acid". Journal of Organic Chemistry. 57 (13): 3731–3732. doi:10.1021/jo00039a043.
  4. D. L. Dull; H. S. Mosher (1967). "Aberrant rotatory dispersion curves of α-hydroxy- and α-methoxy-α-trifluoromethylphenylacetic acids". Journal of the American Chemical Society. 89 (16): 4230. doi:10.1021/ja00992a053.
  5. See for example: Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L. J. Chem. Educ. 2008, 85, 698. Abstract
  6. D. E. Ward; C. K. Rhee (1991). "A simple method for the microscale preparation of Mosher's acid chloride". Tetrahedron Letters. 32 (49): 7165–7166. doi:10.1016/0040-4039(91)80466-J.
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