(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
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 | n |
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) |
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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