13423

(S)-(+)-Glycidyl benzyl ether

puriss., ≥99.0% (sum of enantiomers, GC)

• Synonym(s): (S)-(+)-2-(Benzyloxymethyl)oxirane
• Empirical Formula (Hill Notation): C₁₀H₁₂O₂
• CAS Number: 16495-13-9
• Molecular Weight: 164.20
• Beilstein/REAXYS Number: 5246494
• EC Number: 231-598-3
• MDL number: MFCD00054428
• UNSPSC Code: 12352005
• PubChem Substance ID: 329750167

Properties

• 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

Description

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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 230.0 °F - closed cup
• flash_point_c: 110 °C - closed cup
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter