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MilliporeSigma

727075

Sigma-Aldrich

(R)-(−)-Mandelic acid

ChiPros®, produced by BASF, 99%

Synonym(s):

(R)-α-Hydroxyphenylacetic acid

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About This Item

Linear Formula:
C6H5CH(OH)CO2H
CAS Number:
611-71-2
Molecular Weight:
152.15
Beilstein/REAXYS Number:
2691094
EC Number:
210-276-6
MDL number:
MFCD00064251
UNSPSC Code:
12352106
PubChem Substance ID:
329764292
NACRES:
NA.22

Key Documents

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Quality Level

100

assay

≥98.5%
99%

form

crystals

optical purity

enantiomeric excess: ≥98.5%

mp

131-133 °C (lit.)

functional group

carboxylic acid
hydroxyl
phenyl

SMILES string

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

InChI

1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1

InChI key

IWYDHOAUDWTVEP-SSDOTTSWSA-N

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1 of 4

This Item
154210M2209Y0001285
(R)-(−)-Mandelic acid ChiPros®, produced by BASF, 99%

Sigma-Aldrich

727075

(R)-(−)-Mandelic acid

(R)-(−)-Mandelic acid ReagentPlus®, ≥99%

Sigma-Aldrich

154210

(R)-(−)-Mandelic acid

(R)-(−)-Mandelic acid 98%

Sigma-Aldrich

M2209

(R)-(−)-Mandelic acid

Sertraline impurity E European Pharmacopoeia (EP) Reference Standard

Y0001285

Sertraline impurity E

assay

≥98.5%, 99%

assay

≥99%

assay

98%

assay

-

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

-

form

crystals

form

solid

form

-

form

-

mp

131-133 °C (lit.)

mp

131-133 °C (lit.)

mp

131-133 °C (lit.)

mp

131-133 °C (lit.)

grade

produced by BASF

grade

-

grade

-

grade

pharmaceutical primary standard

optical purity

enantiomeric excess: ≥98.5%

optical purity

-

optical purity

ee: 99% (GLC)

optical purity

-

General description

(R)-(−)-Mandelic acid is a chiral resolving agent, which is also used as a chiral building block in the preparation of semisynthetic cephalosporins, antitumor agents, and penicillins.[1]

Application

(R)-(−)-Mandelic acid can be used:
  • As a chiral acid in the separation of diastereomeric salts for the synthesis of chiral pyridoindole based building block.[2]
  • In the study of chiral acid selectivity of poly(3,4-ethylenedioxythiophene) (PEDOT) based chiral conducting polymers.[3]

Legal Information

ChiPros is a registered trademark of BASF SE

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

>374.0 °F

flash_point_c

> 190 °C

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK8655
BCCH9458
BCBH7332V
BCBH7332

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Chiral acid selectivity displayed by PEDOT electropolymerised in the presence of chiral molecules
Sulaiman Y and Kataky R
Analyst, 137(10), 2386-2393 (2012)
Biocatalytic synthesis of (R)-(−)-mandelic acid from racemic mandelonitrile by a newly isolated nitrilase-producer Alcaligenes sp. ECU0401
He YC, et al.
Chinese Chemical Letters = Zhongguo Hua Xue Kuai Bao, 18(6), 677-680 (2007)
A Short Synthesis of the 2-Bromo-N, 9-dimethyl-6, 7, 8, 9-tetrahydro-5 H-pyrido [2, 3-b] indol-6-amine Building Block
Sreenivasachary N, et al.
Organic Process Research & Development, 23(11), 2521-2526 (2019)
Ling-Bo Gao et al.
Chirality, 24(1), 86-95 (2011-12-06)
Mandelic acid (MA) is generally used as a biological indicator of occupational exposure to styrene, which is classified as a class of hazardous environmental pollutants. It was found to undergo one-directional chiral inversion (S-MA to R-MA) in Wistar and Sprague-Dawley
Quan He et al.
Chirality, 24(2), 119-128 (2011-12-17)
The chiral discrimination mechanism in the resolution of sertraline with mandelic acid was investigated by examining the weak intermolecular interactions (such as hydrogen bond, CH/π, and van der Waals interactions) and molecular packing difference in crystal structures of the resulting
View All Related Papers

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