ChemicalBook Product Catalog Chemical Reagents Organic reagents Ethers (S)-(+)-Benzyl glycidyl ether

(S)-(+)-Benzyl glycidyl ether

(S)-(+)-Benzyl glycidyl ether Basic information
Product Name:(S)-(+)-Benzyl glycidyl ether
Synonyms:(S)-(+)-2-(BENZYLOXYMETHYL)OXIRANE;(S)-(+)-1-BENZYLOXY-2,3-EPOXYPROPANE;(S)-1-BENZYLOXY-2,3-EPOXYPROPANE;(S)-(+)-BENZYL GLYCIDYL ETHER;(S)-BENZYL GLYCIDYL ETHER;(S)-BENZYLOXYMETHYL-OXIRANE;(s)-o-benzylglycidol;(S)-(+)-Glycidyl benzyl ether puriss., >=99.0% (sum of enantiomers, GC)
CAS:16495-13-9
MF:C10H12O2
MW:164.2
EINECS:605-380-7
Product Categories:Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Oxiranes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Compound;chiral;CHIRAL COMPOUNDS
Mol File:16495-13-9.mol
(S)-(+)-Benzyl glycidyl ether Structure
(S)-(+)-Benzyl glycidyl ether Chemical Properties
alpha 5.1 º (c=5 in toluene)
Boiling point 130 °C (0.1 mmHg)
density 1.072 g/mL at 20 °C(lit.)
refractive index n20/D 1.517
Fp >110°C
storage temp. 2-8°C
solubility Chloroform, Ethanol
form Oil
Specific Gravity1.077
color Colourless
optical activity[α]20/D +5.1°, c = 5 in toluene
BRN 5246495
CAS DataBase Reference16495-13-9(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
Toxicitymic-sat 660 nmol/plate MUREAV 298,197,1993
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
(S)-(+)-Benzyl glycidyl ether Usage And Synthesis
Chemical PropertiesColorless 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 ProfileMutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.
Purification MethodsThis 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 Preparation Products And Raw materials
Benzyl chloride (R)-Styrene oxide ETHYLENE OXIDE GLYCIDYL ACRYLATE Benzyl alcohol Ethylbenzene (S)-(-)-Trityl glycidyl ether Polyethylene, Oxidized Diethyl ether Benzyl (S)-(+)-Benzyl glycidyl ether Epichlorohydrin (2R)-(+)-3 3-DIMETHYLGLYCIDYL Dimethyl ether Benzyl benzoate Benzyl nicotinate Isobutylene oxide Propylene oxide
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