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05512

Sigma-Aldrich

(S)-(−)-1-Phenylethanol

≥98.5% (sum of enantiomers, GC)

Synonym(s):

(−)-Methyl phenyl carbinol, (S)-(−)-α-Methylbenzyl alcohol, (S)-(−)-sec-Phenylethyl alcohol

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About This Item

Empirical Formula (Hill Notation):
C8H10O
CAS Number:
Molecular Weight:
122.16
Beilstein:
2039797
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥98.5% (sum of enantiomers, GC)

form

liquid

optical activity

[α]/D −45±2°, c = 5% in methanol

optical purity

enantiomeric ratio: ≥97:3 (GC)

refractive index

n20/D 1.527

bp

88-89 °C/10 mmHg (lit.)

mp

9-11 °C (lit.)

density

1.012 g/mL at 20 °C (lit.)

functional group

hydroxyl
phenyl

SMILES string

C[C@H](O)c1ccccc1

InChI

1S/C8H10O/c1-7(9)8-5-3-2-4-6-8/h2-7,9H,1H3/t7-/m0/s1

InChI key

WAPNOHKVXSQRPX-ZETCQYMHSA-N

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General description

(S)-(-)-1-Phenylethanol can be prepared from acetophenone via enantioselective bioreduction in the presence of Rhizopus arrhizus as a biocatalyst.

Application

(S)-(-)-1-Phenylethanol can be used as:
  • A starting material to prepare (1S,3R,4S)-1-methyl-3,4-diphenyl-3,4-dihydro-1H-isochromene-3,4-diol (a cyclic hemiacetal) by reacting with benzil via dilithiation reaction.
  • A chiral solvent in the symmetric synthesis of substituted spiroundecenetriones via amino acid-catalyzed domino Knoevenagel/Diels-Alder reactions.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Laboratory scale-up synthesis of chiral carbinols using Rhizopus arrhizus
Salvi, NA and Chattopadhyay S
Tetrahedron Asymmetry, 27(4-5), 188-192 (2016)
Synthesis of (1S, 3R, 4S)-1-methyl-3, 4-diphenyl-3, 4-dihydro-1H-isochromene-3, 4-diol
Shishkina IN, et al.
Mendeleev Communications, 6(23), 350-351 (2013)
Organocatalytic Asymmetric Domino Knoevenagel/Diels-Alder Reactions: A Bioorganic Approach to the Diastereospecific and Enantioselective Construction of Highly Substituted Spiro [5, 5] undecane-1, 5, 9-triones
Ramachary DB, et al.
Angewandte Chemie (International Edition in English), 42(35), 4233-4237 (2003)

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