13423
(S)-(+)-Glycidyl benzyl ether
puriss., ≥99.0% (sum of enantiomers, GC)
Synonym(s):
(S)-(+)-2-(Benzyloxymethyl)oxirane
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About This Item
Empirical Formula (Hill Notation):
C10H12O2
CAS Number:
Molecular Weight:
164.20
EC Number:
231-598-3
UNSPSC Code:
12352005
PubChem Substance ID:
Beilstein/REAXYS Number:
5246494
MDL number:
Assay:
≥99.0% (sum of enantiomers, GC)
Form:
solid
grade
puriss.
Quality Level
assay
≥99.0% (sum of enantiomers, GC)
form
solid
optical activity
[α]20/D +5.1±0.5°, c = 5% in toluene
refractive index
n20/D 1.517
density
1.072 g/mL at 20 °C (lit.)
SMILES string
C(OCc1ccccc1)[C@@H]2CO2
InChI
1S/C10H12O2/c1-2-4-9(5-3-1)6-11-7-10-8-12-10/h1-5,10H,6-8H2/t10-/m1/s1
InChI key
QNYBOILAKBSWFG-SNVBAGLBSA-N
General description
(S)-(+)-Glycidyl benzyl ether is aryl glycidyl ether. Enantiomerically pure aryl and benzyl glycidyl ethers have been reported to undergo stereospecific cyclizations, affording 3-chromanols or tetrahydrobenzo[c]oxepin-4-ols. (S)-benzyl glycidyl ether has been produced with 30%ee along with (R)-3-benzyloxypropane-1,2-diol with 40%ee, via its resolution using whole cells of Bacillus alcalophilus.
Application
(S)-(+)-Glycidyl benzyl ether may be employed for the total asymmetric synthesis of (+)-gigantecin.
Other Notes
Important chiral building block reacting with nucleophiles at C-3 of the oxirane ring
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
230.0 °F - closed cup
flash_point_c
110 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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T.M. Avignon et al.
Tetrahedron, 47, 7279-7279 (1991)
Rocío Marcos et al.
Journal of the American Chemical Society, 130(50), 16838-16839 (2008-12-05)
Enantiomerically pure aryl and benzyl glycidyl ethers undergo stereospecific cyclizations leading to 3-chromanols or to tetrahydrobenzo[c]oxepin-4-ols under mild conditions in the presence of a catalytic amount of FeBr3/3AgOTf. The same processes are also mediated, albeit in a much less efficient
R.E. Ireland et al.
The Journal of Organic Chemistry, 55, 1423-1423 (1990)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 13423-1KG-R | 04061838729941 |
| 13423-6X1KG-R | 04061834411123 |
| 13423-5KG-R | 04061834411116 |