Mosher's acid

Summary

Mosher's acid
(S)-Mosher Acid Formula V.1.svg
(R)-Mosher Acid Formula V.1.svg
S-Mosher's-acid-3D-balls.png
R-Mosher's-acid-3D-balls.png
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
  • (racemic): 81655-41-6 checkY
  • (R): 20445-31-2 checkY[PubChem]
  • (S): 17257-71-5 checkY[PubChem]
3D model (JSmol)
  • Interactive image
ChemSpider
  • 78043 ☒N
ECHA InfoCard 100.153.604 Edit this at Wikidata
EC Number
  • (R): 243-829-5
  • (S): 241-292-1
  • (R): 2723917
  • (S): 6992788
UNII
  • (racemic): E015GCC0MA checkY
  • (R): 27O5L9T1WM checkY
  • (S): 172HCJ1IQV checkY
  • DTXSID90897007
  • 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) ☒N
    Key: JJYKJUXBWFATTE-UHFFFAOYSA-N ☒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
  • COC(C(O)=O)(c1ccccc1)C(F)(F)F
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
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
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
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]

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.