(+)-Benzyl glycidyl ether
Basic information
- CAS
16495-13-9- Standard SMILES
c1ccc(COC[C@@H]2CO2)cc1- InChIKey
QNYBOILAKBSWFG-SNVBAGLBSA-N- Molecular formula
- C10H12O2
- Average molar mass
- 164.2 g/mol
- Monoisotopic mass
- 164.08372962
Names & identifiers
- Preferred name
- (+)-Benzyl glycidyl ether
- IUPAC
- (2S)-2-(phenylmethoxymethyl)oxirane
- English name
- (S)-(+)-Benzyl glycidyl ether
- Molecular formula
- C10H12O2
- Molecular weight
- 164.2
Names & synonyms
(+)-Benzyl glycidyl ether(S)-(+)-Glycidyl Benzyl EtherRefChem:390572605-380-716495-13-9Benzyl (S)-(+)-Glycidyl Ether(S)-2-((Benzyloxy)methyl)oxirane(S)-Benzyloxymethyl-oxirane(S)-(+)-Benzyl glycidyl ether(2S)-2-[(benzyloxy)methyl]oxirane(S)-Benzyl glycidyl ether(2S)-2-(benzyloxymethyl)oxirane
Show more names
(S)-Benzylglycidyether(S)-Glycidylbenzyl ether(+)-BENZYL (S)-GLYCIDYL ETHER
(S)-O-BenzylglycidolS-Benzylglycidyl etherMFCD00054428(S)-benzyloxymethyloxiraneO-benzyl-glycidol(2S)-2-(phenylmethoxymethyl)oxiraneOxirane, 2-[(phenylmethoxy)methyl]-, (2S)-(S)-benzylglycidyl ether
Database identifiers
- CAS
16495-13-9- PubChem CID
- 146296
- DTXSID
DTXSID20167826- EC Number
- 605-380-7
- Nikkaji
- J81.789I
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 21.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 130
Physicochemical properties
- Boiling point
- 130 °C · 130 °C (0.1 mmHg)
- alpha
- 5.1 · 5.1 º (c=5 in toluene)
- Density
- 1.072 g/mL · 1.072 g/mL at 20 °C(lit.)
- refractive index
- 20 · n20/D 1.517
- Flash point
- 110 °C · >110°C
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform, Ethanol
- form
- Oil
- color
- Colourless
- Specific Gravity
- 1.077 · 1.077
- optical activity
- 20 · [α]20/D +5.1°, c = 5 in toluene
- BRN
- 5246495 · 5246495
- InChI
- 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
- InChIKey
- QNYBOILAKBSWFG-SNVBAGLBSA-N
- SMILES
- O1C[C@H]1COCC1=CC=CC=C1
- CAS DataBase Reference
- 16495 · 16495-13-9(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 47 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- rtecs
- TX2860030
- hs_code
- 29109000
- Toxicity
- mic-sat 660 nmol/plate MUREAV 298,197,1993
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 10 - Combustible liquids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
Chemistry & industry
Applications
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.
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Related reactions
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Compound notes
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