Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

253030

Sigma-Aldrich

(R)-(−)-O-Acetylmandelic acid

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

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Linear Formula:
CH3CO2CH(C6H5)CO2H
CAS Number:
51019-43-3
Molecular Weight:
194.18
Beilstein:
2694110
MDL number:
MFCD00004249
UNSPSC Code:
12352108
PubChem Substance ID:
24855256
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000234172
BGBC4601V
MKBJ2684V
08605EJ
00210MD

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
An efficient synthesis of chiral nonracemic diamines: application in asymmetric synthesis.
Saravanan P and Singh VK.
Tetrahedron Letters, 39(1), 167-170 (1998)
Tritiated chiral alkanes as substrates for soluble methane monooxygenase from Methylococcus capsulatus (Bath): probes for the mechanism of hydroxylation.
Valentine AM, et al.
Journal of the American Chemical Society, 119(8), 1818-1827 (1997)
J. Chem. Soc. Perkin Trans. II, 83-83 (1983)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service