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
CAS Number	81655-41-6 (racemic); 20445-31-2 (R); 17257-71-5 (S);
3D model (JSmol)	Interactive image;
ChemSpider	78043;
ECHA InfoCard	100.153.604
CompTox Dashboard (EPA)	DTXSID90897007 ;
	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
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 [77 °F], 100 kPa). verify (what is ?) 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

^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.
^ 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.
^ 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.
^ 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
^ 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.

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.

[1]

[2]

[3]

[4]

[5]

[6]

Applications

See also

References