Mosher's acid

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
81655-41-6 (racemic)
20445-31-2 (R)
17257-71-5 (S)
ChemSpider 78043
Jmol interactive 3D Image
Properties
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
R-phrases R36/37/38
S-phrases S26/S36
Flash point 110 °C (230 °F; 383 K)
Related compounds
Mosher's acid chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1][2][3][4] It is a chiral molecule, consisting of R and S enantiomers.

Applications

As a chiral derivatizing agent, it reacts with an alcohol or amine[5] 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.

Mosher's acid chloride, the acid chloride form, is sometimes used because it has better reactivity.[6]

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): 4230–4230. 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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