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155268

Sigma-Aldrich

(R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid

99%

Synonym(s):

(+)-MTPA, Mosher’s acid

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About This Item

Linear Formula:
C6H5C(OCH3)(CF3)CO2H
CAS Number:
20445-31-2
Molecular Weight:
234.17
Beilstein/REAXYS Number:
3591560
EC Number:
243-829-5
MDL number:
MFCD00004184
UNSPSC Code:
12352112
PubChem Substance ID:
24849508
NACRES:
NA.22

Key Documents

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Quality Level

100

assay

99%

form

solid

optical activity

[α]20/D +72°, c = 1.6 in methanol

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.473 (lit.)

bp

105-107 °C/1 mmHg (lit.)

mp

46-49 °C (lit.)

density

1.344 g/mL at 25 °C (lit.)

functional group

carboxylic acid
ether
fluoro
phenyl

storage temp.

2-8°C

SMILES string

CO[C@@](C(O)=O)(c1ccccc1)C(F)(F)F

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)/t9-/m1/s1

InChI key

JJYKJUXBWFATTE-SECBINFHSA-N

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This Item
65365M2876318035
(R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid 99%

Sigma-Aldrich

155268

(R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid

(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride derivatization grade (chiral), LiChropur™, ≥99.0%

Supelco

65365

(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride

(±)-α-Methoxyphenylacetic acid crystalline

Sigma-Aldrich

M2876

(±)-α-Methoxyphenylacetic acid

(S)-(−)-α-Methoxy-α-(trifluoromethyl)phenylacetic acid ≥99%

Sigma-Aldrich

318035

(S)-(−)-α-Methoxy-α-(trifluoromethyl)phenylacetic acid

assay

99%

assay

≥99.0% (AT)

assay

≥99.0%

assay

≥99%

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

200

refractive index

n20/D 1.473 (lit.)

refractive index

n20/D 1.469 (lit.)

refractive index

-

refractive index

n20/D 1.474 (lit.)

density

1.344 g/mL at 25 °C (lit.)

density

1.35 g/mL at 25 °C (lit.)

density

-

density

1.303 g/mL at 25 °C (lit.)

form

solid

form

-

form

crystalline

form

-

bp

105-107 °C/1 mmHg (lit.)

bp

213-214 °C (lit.)

bp

165 °C ((lit.)), 165 °C/18 mmHg (lit.)

bp

95-97 °C/0.05 mmHg (lit.)

Application

(R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid is commonly used as a derivatizing agent in Mosher ester analysis, an NMR-based method for determining the absolute configuration of the chiral carbon center in a secondary alcohol.[1]

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

doi:10.1038/nprot.2007.354

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF7003
BCBM7115V
1374690V
1358876V
1374690

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Lidia De Luca et al.
The Journal of organic chemistry, 72(10), 3955-3957 (2007-04-11)
An effective route to chiral optically active 2-substituted benzofurans directly from carboxylic acids is reported. This procedure, which allows the preparation of alpha-alkyl-2-benzofuranmethanamines from N-protected alpha-amino acids without sensible racemization phenomena, proceeds in good yields under mild conditions with the
Tetrahedron Asymmetry, 18, 975-975 (2007)
Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.
Hoye TR, et al.
Nature Protocols, 2(10), 2451-2458 (2007)
Bin Sui et al.
The Journal of organic chemistry, 75(9), 2942-2954 (2010-04-17)
Two different mixture synthesis routes have been used to make the four stereoisomers of petrocortyne A. A first quick and dirty route provided a mixture of the four isomers in nonselective fashion. Mosher and 2-naphthylmethoxyacetic acid (NMA) ester methods were
D B Matthews et al.
Journal of chromatography. B, Biomedical sciences and applications, 695(2), 279-285 (1997-08-01)
Methods for the nuclear magnetic resonance and gas chromatographic analysis of the enantiomers of p-trifluoromethylmandelic acid (p-TFM) and Mosher's acid (alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid) present in rat urine samples are described. Gas chromartography was performed using cyclodextrin capillary columns with both compounds
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