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{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 405332765
| Watchedfields = changed
| verifiedrevid = 428793132
| Name = Mosher's acid | Name = Mosher's acid
| ImageFileR1 = R-MTPA.png | ImageFileR1 = (R)-Mosher Acid Formula V.1.svg

<!-- | ImageSize = 150px -->
| ImageName = | ImageName =
| ImageFileL1 = S-MTPA.png | ImageFileL1 = (S)-Mosher Acid Formula V.1.svg

<!-- | ImageSize1 = 150px -->
| ImageFileR2 = R-Mosher's-acid-3D-balls.png | ImageFileR2 = R-Mosher's-acid-3D-balls.png
| ImageFileL2 = S-Mosher's-acid-3D-balls.png | ImageFileL2 = S-Mosher's-acid-3D-balls.png
| IUPACName = (R/S)-3,3,3-trifluoro-2-<br />methoxy-2-phenylpropanoic acid | IUPACName =(''R'')-3,3,3-trifluoro-2-<wbr />methoxy-2-phenylpropanoic acid<br/>
(''S'')-3,3,3-trifluoro-2-<wbr />methoxy-2-phenylpropanoic acid
| OtherNames = Methoxy(trifluoromethyl)phenylacetic acid, MTPA | OtherNames = Methoxy(trifluoromethyl)phenylacetic acid, MTPA
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| SMILES = COC(C(O)=O)(c1ccccc1)C(F)(F)F | SMILES = COC(C(O)=O)(c1ccccc1)C(F)(F)F
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo=81655-41-6 | CASNo1 = 81655-41-6
| CASOther = (racemic) <br/> (R)<br /> (S)
| index1_label = (racemic)
| CASNo2_Ref = {{cascite|correct|PubChem}}
| CASNo2 = 20445-31-2
| index2_label = (''R'')
| CASNo3_Ref = {{cascite|correct|PubChem}}
| CASNo3 = 17257-71-5
| index3_label = (''S'')
| PubChem2 = 2723917
| PubChem3 = 6992788
| EC_number2 = 243-829-5
| EC_number3 = 241-292-1
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII3_Ref = {{fdacite|correct|FDA}}
| UNII3 = 172HCJ1IQV
| UNII2 = 27O5L9T1WM
| UNII1 = E015GCC0MA
| DTXSID = DTXSID90897007
| RTECS = | RTECS =
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 78043
| 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)
| InChIKey = JJYKJUXBWFATTE-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = JJYKJUXBWFATTE-UHFFFAOYSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>9</sub>F<sub>3</sub>O<sub>3</sub> | Formula = C<sub>10</sub>H<sub>9</sub>F<sub>3</sub>O<sub>3</sub>
| MolarMass = 234.17 | MolarMass = 234.17
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| Density = | Density =
| Solubility = | Solubility =
| MeltingPt = 46-49°C (319-322 K) | MeltingPtC = 46 to 49
| MeltingPt_notes =
| BoilingPt = 105 - 107 °C at 1 torr<!-- 116-118 °C -->
| BoilingPtC = 105 to 107
| BoilingPt_notes = at 1 torr<!-- 116-118 °C -->
| pKa = | pKa =
| pKb = | pKb =
| Viscosity = | Viscosity =
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| FlashPt = 110°C | FlashPtC = 110
| RPhrases = {{R36/37/38}} | GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| SPhrases = {{S26-36}}
| HPhrases = {{H-phrases|315|319|335}}
}}
| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
| Section8 = {{Chembox Related
| Function = ]
| OtherFunctn = ]
| OtherCpds =
}} }}
|Section8={{Chembox Related
| OtherFunction_label = ]
| OtherFunction = ]
| OtherCompounds =
}}
}} }}


'''Mosher's acid''', or '''α-methoxy-α-trifluoromethylphenylacetic acid (MTPA)''' is a ] which was first used by ] as a ].<ref>{{cite journal '''Mosher's acid''', or '''α-methoxy-α-trifluoromethylphenylacetic acid''' ('''MTPA''') is a ] which was first used by ] as a ].<ref>{{cite journal
|author1=J. A. Dale |author2=D. L. Dull |author3=H. S. Mosher | title = α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines
| author = J. A. Dale, D. L. Dull, H. S. Mosher
| title = α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines
| journal = ] | journal = ]
| year = 1969 | year = 1969
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| doi = 10.1021/jo01261a013 | doi = 10.1021/jo01261a013
}}</ref><ref>{{cite journal }}</ref><ref>{{cite journal
|author1=J. A. Dale |author2=H. S. Mosher | title = 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
| author = J. A. Dale, H. S. Mosher
| title = 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 = ] | journal = ]
| year = 1973 | year = 1973
| volume = 95 | volume = 95
| issue = 2 | issue = 2
| pages = 512–519 | pages = 512–519
| doi = 10.1021/ja00783a034 | doi = 10.1021/ja00783a034
}}</ref><ref>{{cite journal }}</ref><ref>{{cite journal
| author = Y. Goldberg, H. Alper |author1=Y. Goldberg |author2=H. Alper | title = A new and simple synthesis of Mosher's acid
| title = A new and simple synthesis of Mosher's acid
| journal = ] | journal = ]
| year = 1992 | year = 1992
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| doi = 10.1021/jo00039a043 | doi = 10.1021/jo00039a043
}}</ref><ref>{{cite journal }}</ref><ref>{{cite journal
|author1=D. L. Dull |author2=H. S. Mosher | title = Aberrant rotatory dispersion curves of α-hydroxy- and α-methoxy-α-trifluoromethylphenylacetic acids
| author = D. L. Dull, H. S. Mosher
| title = Aberrant rotatory dispersion curves of α-hydroxy- and α-methoxy-α-trifluoromethylphenylacetic acids
| journal = ] | journal = ]
| year = 1967 | year = 1967
| volume = 89 | volume = 89
| issue = 16 | issue = 16
| pages = 4230–4230 | pages = 4230
| doi = 10.1021/ja00992a053 | doi = 10.1021/ja00992a053
}}</ref> It is a chiral molecule, consisting of R and S enantiomers. }}</ref> It is a ] molecule, consisting of ''R'' and ''S'' enantiomers.


==Applications== ==Applications==
As a chiral derivatizing agent, it reacts with an ] or ]<ref>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. ] '''2008''', 85, 698. </ref> of unknown ] to form an ester or amide. The ] of the ester or amide is then determined by proton and/or ] ]. As a chiral derivatizing agent, it reacts with an ] or ]<ref>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. ] '''2008''', 85, 698. </ref> of unknown ] to form an ester or amide. The ] of the ester or amide is then determined by proton and/or ] ].


'''Mosher's acid chloride''', the ] form, is sometimes used because it has better reactivity.<ref>{{cite journal '''Mosher's acid chloride''', the ] form, is sometimes used because it has better reactivity.<ref>{{cite journal
|author1=D. E. Ward |author2=C. K. Rhee | title = A simple method for the microscale preparation of Mosher's acid chloride
| author = D. E. Ward, C. K. Rhee
| title = A simple method for the microscale preparation of Mosher's acid chloride
| journal = ] | journal = ]
| year = 1991 | year = 1991
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| doi = 10.1016/0040-4039(91)80466-J | doi = 10.1016/0040-4039(91)80466-J
}}</ref> }}</ref>

== See also ==
* ]


==References== ==References==
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