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Merck
CN

63450

Sigma-Aldrich

D-(−)-Mandelic acid

puriss., ≥99.0% (T)

Synonym(s):

(R)-α-Hydroxyphenylacetic acid

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About This Item

Empirical Formula (Hill Notation):
C8H8O3
CAS Number:
Molecular Weight:
152.15
Beilstein:
2691094
EC Number:
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
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grade

puriss.

Assay

≥99.0% (T)

optical activity

[α]20/D −155±5°, c = 5% in H2O

optical purity

enantiomeric ratio: ≥99:1 (GC)

mp

130-133 °C

SMILES string

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

InChI

1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1

InChI key

IWYDHOAUDWTVEP-SSDOTTSWSA-N

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Other Notes

Reagent used for the resolution of bases; Resolution of alcohols via esters; Stereoselective α-alkylation via dioxolanones

Regulatory Information

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S.H. Wilen
Topics in Stereochemistry, vol. 6 (1971)
K. Saigo et al.
Bulletin of the Chemical Society of Japan, 59, 931-931 (1986)
R. Fitzi et al.
Angewandte Chemie (International Edition in English), 98, 363-363 (1986)
J.K. Whitesell et al.
The Journal of Organic Chemistry, 48, 3548-3548 (1983)
D. Seebach et al.
Tetrahedron, 40, 1313-1313 (1984)

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