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253030

(R)-(−)-O-Acetylmandelic acid

Name: (<I>R</I>)-(−)-<I>O</I>-Acetylmandelic acid
Brand: ALDRICH

99%, optical purity ee: 98% (GLC)

Synonym(s):

(−)-O-Acetyl-D-mandelic acid, (R)-(−)-α-Acetoxyphenylacetic acid

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About This Item

Linear Formula:

CH₃CO₂CH(C₆H₅)CO₂H

CAS Number:

51019-43-3

Molecular Weight:

194.18

UNSPSC Code:

12352108

NACRES:

NA.22

PubChem Substance ID:

24855256

MDL number:

MFCD00004249

Beilstein/REAXYS Number:

2694110

Assay:

99%

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Properties

Quality Level

200

assay

99%

optical activity

[α]20/D −152.4°, c = 2 in acetone

optical purity

ee: 98% (GLC)

mp

97-99 °C (lit.)

functional group

carboxylic acid, ester, phenyl

SMILES string

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

InChI

1S/C10H10O4/c1-7(11)14-9(10(12)13)8-5-3-2-4-6-8/h2-6,9H,1H3,(H,12,13)/t9-/m1/s1

InChI key

OBCUSTCTKLTMBX-SECBINFHSA-N

Description

General description

(R)-(-)-O-Acetylmandelic acid is a chiral derivatizing agent for NMR determination of enantiomeric purity of α-deuterated carboxylic acids, alcohols, and amines.

Application

(R)-(-)-O-Acetylmandelic acid may be used as a precursor to prepare a chiral diamine, which is an intermediate to prepare Utenone A. It may also be used to prepare ethyl (2′R)-2′-acetoxy-2′-phenylethanoate.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000470329

0000234172

0000113112

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An efficient synthesis of chiral nonracemic diamines: application in asymmetric synthesis.

Saravanan P and Singh VK.

Tetrahedron Letters, 39(1), 167-170 (1998)

Chiroptical features and luminescence behaviour of macrocyclic tetra (4-quinolyl)-complexes: surprising absence of exciton coupling.

Govenlock L, et al.

J. Chem. Soc. Perkin Trans. II, 11, 2415-2418 (1999)

Modular ligand variation in calcium bisimidazoline complexes: effects on ligand redistribution and hydroamination catalysis.

Wixey JS and Ward BD.

Dalton Transactions, 40(30), 7693-7696 (2011)

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Global Trade Item Number

SKU	GTIN
253030-5G	04061832727998