Skip to Content
Merck

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


About This Item

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

Pricing and availability is not currently available.

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

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
727075154210248967
mp

97-99 °C (lit.)

mp

131-133 °C (lit.)

mp

131-133 °C (lit.)

mp

66-68 °C (lit.)

optical activity

[α]20/D −152.4°, c = 2 in acetone

optical activity

-

optical activity

[α]23/D −153°, c = 2.5 in H2O

optical activity

[α]20/D −146°, c = 0.5 in ethanol

optical purity

ee: 98% (GLC)

optical purity

enantiomeric excess: ≥98.5%

optical purity

-

optical purity

-

functional group

carboxylic acid

functional group

carboxylic acid, hydroxyl, phenyl

functional group

-

functional group

carboxylic acid, ether, phenyl

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.[1]

Application

(R)-(-)-O-Acetylmandelic acid may be used as a precursor to prepare a chiral diamine, which is an intermediate to prepare Utenone A.[2] It may also be used to prepare ethyl (2′R)-2′-acetoxy-2′-phenylethanoate.[3]

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

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.

Already Own This Product?

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

Visit the Document Library

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)
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)
An efficient synthesis of chiral nonracemic diamines: application in asymmetric synthesis.
Saravanan P and Singh VK.
Tetrahedron Letters, 39(1), 167-170 (1998)
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