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HomeProduct name list(S)-(+)-Benzyl glycidyl ether

(S)-(+)-Benzyl glycidyl ether

Synonym(s):(S)-(+)-2-(Benzyloxymethyl)oxirane

  • CAS NO.:16495-13-9
  • Empirical Formula: C10H12O2
  • Molecular Weight: 164.2
  • MDL number: MFCD00054428
  • EINECS: 605-380-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-21 22:41:43
(S)-(+)-Benzyl glycidyl ether Structural

What is (S)-(+)-Benzyl glycidyl ether?

Chemical properties

Colorless to light yellow liqui

The Uses of (S)-(+)-Benzyl glycidyl ether

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

The Uses of (S)-(+)-Benzyl glycidyl ether

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

What are the applications of Application

(S)-(+)-Glycidyl benzyl ether is an important chiral building block

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.]

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

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 for (S)-(+)-Benzyl glycidyl ether

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for (S)-(+)-Benzyl glycidyl ether

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