253030
(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:
Molecular Weight:
194.18
Beilstein:
2694110
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22
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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
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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
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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)
Chiroptical features and luminescence behaviour of macrocyclic tetra (4-quinolyl)-complexes: surprising absence of exciton coupling.
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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)
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