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65209

Supelco

(R)-(−)-α-Methoxyphenylacetic acid

for chiral derivatization, LiChropur™, ≥99.0%

Synonym(s):

O-Methyl-D-mandelic acid

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About This Item

Linear Formula:
C6H5CH(OCH3)CO2H
CAS Number:
3966-32-3
Molecular Weight:
166.17
Beilstein/REAXYS Number:
2209198
EC Number:
223-580-9
MDL number:
MFCD00004250
UNSPSC Code:
12000000
PubChem Substance ID:
329760040
NACRES:
NA.22

grade

for chiral derivatization

Quality Level

100

assay

≥99.0% (T)
≥99.0%

form

solid

optical activity

[α]20/D -150±3°, c = 0.5% in ethanol

optical purity

enantiomeric ratio: ≥99.5:0.5 (GC)

quality

LiChropur™

technique(s)

HPLC: suitable

mp

64-67 °C
66-68 °C (lit.)

SMILES string

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

InChI

1S/C9H10O3/c1-12-8(9(10)11)7-5-3-2-4-6-7/h2-6,8H,1H3,(H,10,11)/t8-/m1/s1

InChI key

DIWVBIXQCNRCFE-MRVPVSSYSA-N

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General description

(R)-(−)-α-Methoxyphenylacetic acid is a chiral derivatizating agent, which is employed for derivatizing enantiomers into diastereoisomers.

Other Notes

Chiral reagent for the det. of enantiomeric purity and absolute configuration of sec-alcohols and α-chiral amines by NMR; Analysis of amines using the ONSu ester

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Legal Information

LiChropur is a trademark of Merck KGaA, Darmstadt, Germany

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

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
1230686
044551/1
017320/1
44551/1
061617/1

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P A Husain et al.
Analytical biochemistry, 178(1), 177-183 (1989-04-01)
A chiral derivatizing reagent, N-succinimidyl-2-(S)-methoxy-2-phenylacetic acid ester (SMPA), directed toward reaction with primary amine-containing compounds has been synthesized and characterized. This reagent is suitable for HPLC resolution from enzymatic-scale reactions where only microgram quantities of chiral products may be obtainable.
The Journal of Organic Chemistry, 59, 4202-4202 (1994)
B.M. Trost et al.
The Journal of Organic Chemistry, 51, 2370-2370 (1986)
P A Husain et al.
Analytical chemistry, 65(10), 1456-1461 (1993-05-15)
We introduce a novel, HPLC-based method for facile determination of the absolute configuration of alpha-chiral amines. Our method is easily applied to a variety of compounds, including amino acid derivatives. The method involves initial derivatization of the chiral amine analyte
Radoslaw Laufer et al.
Bioorganic & medicinal chemistry, 22(17), 4968-4997 (2014-07-22)
TTK kinase was identified by in-house siRNA screen and pursued as a tractable, novel target for cancer treatment. A screening campaign and systematic optimization, supported by computer modeling led to an indazole core with key sulfamoylphenyl and acetamido moieties at

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