05512
(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
UNSPSC Code:
12352002
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2039797
Assay:
≥98.5% (sum of enantiomers, GC)
Form:
liquid
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
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.
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Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2
wgk
WGK 3
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Articles
Chiral Alcohols
Laboratory scale-up synthesis of chiral carbinols using Rhizopus arrhizus
Salvi, NA and Chattopadhyay S
Tetrahedron Asymmetry, 27(4-5), 188-192 (2016)
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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 220051-25G | 04061838776211 |
| 220051-5G | 04061838776228 |
| 220051-100G | 04061838776204 |
| 05512-5G-F | 04061838637666 |
| 05512-25G-F | 04061837638671 |