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Merck
CN

13423

Sigma-Aldrich

(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:
16495-13-9
Molecular Weight:
164.20
Beilstein:
5246494
EC Number:
231-598-3
MDL number:
MFCD00054428
UNSPSC Code:
12352005
PubChem Substance ID:
329750167

Key Documents

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grade

puriss.

Quality Level

200

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

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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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
1362368V
1362368

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R.E. Ireland et al.
The Journal of Organic Chemistry, 55, 1423-1423 (1990)
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
B.H. Lipshutz et al.
Organic Syntheses, 69, 80-80 (1990)
S. Takano et al.
Tetrahedron Letters, 31, 3619-3619 (1990)
M. Honda et al.
Chemical & Pharmaceutical Bulletin, 39, 1385-1385 (1991)
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