(S)-(+)-Benzyl glycidyl ether Chemical Properties

Boiling point:

130 °C (0.1 mmHg)

alpha 

5.1 º (c=5 in toluene)

Density 

1.072 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.517

Flash point:

>110°C

storage temp. 

2-8°C

solubility 

Chloroform, Ethanol

form 

Oil

color 

Colourless

Specific Gravity

1.077

optical activity

[α]20/D +5.1°, c = 5 in toluene

BRN 

5246495

CAS DataBase Reference

16495-13-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

TX2860030

HS Code 

29109000

Toxicity

mic-sat 660 nmol/plate MUREAV 298,197,1993

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(S)-(+)-Benzyl glycidyl ether Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

(S)-(+)-Benzyl Glycidyl Ether is used as a reactant in the synthesis of (+)-Discodermolide.

Uses

(S)-(+)-Glycidyl benzyl ether may be employed for the total asymmetric synthesis of (+)-gigantecin.

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.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

Purification Methods

This ether in EtOAc is dried (Na2SO4), then purified by flash chromatography using pet ether/EtOAc (5:1) as eluent. The ether distils through a short path distillation apparatus (Kügelrohr) as a colourless liquid. Alternatively, dissolve it in CHCl3, wash it with H2O, dry (Na2SO4), evaporate and purify by silica gel chromatography. [Anisuzzamen & Owen J Chem Soc 1021 1967, Takano et al. Heterocycles 1 6 381 1981, Lipshutz et al. Org Synth 69 82 1990, Takano et al. Synthesis 539 1989, Honda et al. Chem Pharm Bull Jpn 39 1385 1991, Beilstein 12 IV 2277.]

(S)-(+)-Benzyl glycidyl ether(16495-13-9)Related Product Information

• Epichlorohydrin
• Isobutylene oxide
• Glycidyl acrylate
• (R)-Styrene oxide
• Benzyl benzoate
• Propylene oxide
• Ethylbenzene
• Polyethylene, Oxidized
• Dimethyl ether
• ETHYLENE OXIDE
• Benzyl alcohol
• Benzyl chloride
• Benzyl nicotinate
• Diethyl ether
• Benzyl
• (S)-(-)-Trityl glycidyl ether
• (R)-(-)-BENZYL GLYCIDYL ETHER,(R)-BENZYL GLYCIDYL ETHER,(R)-(-)-BENZYL GLYCIDYL ETHER, 98+%
• BENZYL GLYCIDYL ETHER