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{{chembox |
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{{chembox |
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| verifiedrevid = 405332765 |
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| Watchedfields = changed |
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| verifiedrevid = 428793132 |
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| Name = Mosher's acid |
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| Name = Mosher's acid |
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| ImageFileR1 = R-MTPA.png |
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| ImageFileR1 = (R)-Mosher Acid Formula V.1.svg |
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<!-- | ImageSize = 150px --> |
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| ImageName = |
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| ImageName = |
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| ImageFileL1 = S-MTPA.png |
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| ImageFileL1 = (S)-Mosher Acid Formula V.1.svg |
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<!-- | ImageSize1 = 150px --> |
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| ImageFileR2 = R-Mosher's-acid-3D-balls.png |
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| ImageFileR2 = R-Mosher's-acid-3D-balls.png |
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| ImageFileL2 = S-Mosher's-acid-3D-balls.png |
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| ImageFileL2 = S-Mosher's-acid-3D-balls.png |
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| IUPACName = (R/S)-3,3,3-trifluoro-2-<br />methoxy-2-phenylpropanoic acid |
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| IUPACName =(''R'')-3,3,3-trifluoro-2-<wbr />methoxy-2-phenylpropanoic acid<br/> |
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(''S'')-3,3,3-trifluoro-2-<wbr />methoxy-2-phenylpropanoic acid |
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| OtherNames = Methoxy(trifluoromethyl)phenylacetic acid, MTPA |
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| OtherNames = Methoxy(trifluoromethyl)phenylacetic acid, MTPA |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| SMILES = COC(C(O)=O)(c1ccccc1)C(F)(F)F |
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| SMILES = COC(C(O)=O)(c1ccccc1)C(F)(F)F |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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| CASNo=81655-41-6 |
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| CASNo1 = 81655-41-6 |
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| CASOther = (racemic) <br/> (R)<br /> (S) |
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| index1_label = (racemic) |
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| CASNo2_Ref = {{cascite|correct|PubChem}} |
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| CASNo2 = 20445-31-2 |
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| index2_label = (''R'') |
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| CASNo3_Ref = {{cascite|correct|PubChem}} |
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| CASNo3 = 17257-71-5 |
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| index3_label = (''S'') |
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| PubChem2 = 2723917 |
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| PubChem3 = 6992788 |
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| EC_number2 = 243-829-5 |
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| EC_number3 = 241-292-1 |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| UNII3_Ref = {{fdacite|correct|FDA}} |
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| UNII3 = 172HCJ1IQV |
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| UNII2 = 27O5L9T1WM |
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| UNII1 = E015GCC0MA |
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| DTXSID = DTXSID90897007 |
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| RTECS = |
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| RTECS = |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 78043 |
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| 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) |
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| InChIKey = JJYKJUXBWFATTE-UHFFFAOYAJ |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = JJYKJUXBWFATTE-UHFFFAOYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>9</sub>F<sub>3</sub>O<sub>3</sub> |
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| Formula = C<sub>10</sub>H<sub>9</sub>F<sub>3</sub>O<sub>3</sub> |
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| MolarMass = 234.17 |
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| MolarMass = 234.17 |
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| Density = |
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| Density = |
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| Solubility = |
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| Solubility = |
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| MeltingPt = 46-49°C (319-322 K) |
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| MeltingPtC = 46 to 49 |
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| MeltingPt_notes = |
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| BoilingPt = 105 - 107 °C at 1 torr<!-- 116-118 °C --> |
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| BoilingPtC = 105 to 107 |
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| BoilingPt_notes = at 1 torr<!-- 116-118 °C --> |
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| pKa = |
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| pKa = |
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| pKb = |
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| pKb = |
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| Viscosity = |
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| Viscosity = |
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}} |
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}} |
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| Section3 = {{Chembox Structure |
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|Section3={{Chembox Structure |
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| Dipole = |
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| Dipole = |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = 110°C |
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| FlashPtC = 110 |
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| RPhrases = {{R36/37/38}} |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| SPhrases = {{S26-36}} |
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| HPhrases = {{H-phrases|315|319|335}} |
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}} |
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| 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}} |
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| Section8 = {{Chembox Related |
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| Function = ] |
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| OtherFunctn = ] |
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| OtherCpds = |
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|Section8={{Chembox Related |
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| OtherFunction_label = ] |
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| OtherFunction = ] |
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| OtherCompounds = |
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}} |
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}} |
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'''Mosher's acid''', or '''α-methoxy-α-trifluoromethylphenylacetic acid (MTPA)''' is a ] which was first used by ] as a ].<ref>{{cite journal |
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'''Mosher's acid''', or '''α-methoxy-α-trifluoromethylphenylacetic acid''' ('''MTPA''') is a ] which was first used by ] as a ].<ref>{{cite journal |
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|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 |
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| author = J. A. Dale, D. L. Dull, H. S. Mosher |
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| title = α-Methoxy-α-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines |
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| journal = ] |
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| journal = ] |
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| year = 1969 |
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| year = 1969 |
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| doi = 10.1021/jo01261a013 |
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| doi = 10.1021/jo01261a013 |
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}}</ref><ref>{{cite journal |
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}}</ref><ref>{{cite journal |
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|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 |
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| author = J. A. Dale, H. S. Mosher |
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| 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 |
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| journal = ] |
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| journal = ] |
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| year = 1973 |
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| year = 1973 |
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| volume = 95 |
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| volume = 95 |
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| issue = 2 |
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| issue = 2 |
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| pages = 512–519 |
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| pages = 512–519 |
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| doi = 10.1021/ja00783a034 |
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| doi = 10.1021/ja00783a034 |
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}}</ref><ref>{{cite journal |
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}}</ref><ref>{{cite journal |
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| author = Y. Goldberg, H. Alper |
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|author1=Y. Goldberg |author2=H. Alper | title = A new and simple synthesis of Mosher's acid |
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| title = A new and simple synthesis of Mosher's acid |
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| journal = ] |
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| journal = ] |
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| year = 1992 |
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| year = 1992 |
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| doi = 10.1021/jo00039a043 |
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| doi = 10.1021/jo00039a043 |
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}}</ref><ref>{{cite journal |
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}}</ref><ref>{{cite journal |
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|author1=D. L. Dull |author2=H. S. Mosher | title = Aberrant rotatory dispersion curves of α-hydroxy- and α-methoxy-α-trifluoromethylphenylacetic acids |
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| author = D. L. Dull, H. S. Mosher |
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| title = Aberrant rotatory dispersion curves of α-hydroxy- and α-methoxy-α-trifluoromethylphenylacetic acids |
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| journal = ] |
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| journal = ] |
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| year = 1967 |
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| year = 1967 |
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| volume = 89 |
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| volume = 89 |
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| issue = 16 |
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| issue = 16 |
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| pages = 4230–4230 |
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| pages = 4230 |
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| doi = 10.1021/ja00992a053 |
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| doi = 10.1021/ja00992a053 |
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}}</ref> It is a chiral molecule, consisting of R and S enantiomers. |
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}}</ref> It is a ] molecule, consisting of ''R'' and ''S'' enantiomers. |
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==Applications== |
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==Applications== |
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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 ] ]. |
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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 ] ]. |
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'''Mosher's acid chloride''', the ] form, is sometimes used because it has better reactivity.<ref>{{cite journal |
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'''Mosher's acid chloride''', the ] form, is sometimes used because it has better reactivity.<ref>{{cite journal |
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|author1=D. E. Ward |author2=C. K. Rhee | title = A simple method for the microscale preparation of Mosher's acid chloride |
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| author = D. E. Ward, C. K. Rhee |
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| title = A simple method for the microscale preparation of Mosher's acid chloride |
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| journal = ] |
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| journal = ] |
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| year = 1991 |
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| year = 1991 |
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| doi = 10.1016/0040-4039(91)80466-J |
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| doi = 10.1016/0040-4039(91)80466-J |
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}}</ref> |
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}}</ref> |
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== See also == |
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* ] |
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==References== |
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==References== |
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