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Sigma-Aldrich

(R)-(−)-O-Acetylmandelic acid

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
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.)

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

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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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
J. Chem. Soc. Perkin Trans. II, 83-83 (1983)
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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