5-Benzyloxyindole
Synonym(s):NSC 62895
- CAS NO.：1215-59-4
- Empirical Formula: C15H13NO
- Molecular Weight: 223.27
- MDL number: MFCD00005676
- EINECS: 214-930-1
- SAFETY DATA SHEET (SDS)
- Update Date: 2026-01-13 11:13:03
What is 5-Benzyloxyindole?
Chemical properties
Off-white to beige powder
The Uses of 5-Benzyloxyindole
5-Benzyloxyindole is used as reagent/reactant in regioselective preparation of CF3-β-tryptamine derivatives via base-free thermal ring-opening reaction of N-nosyl-2-CF3-aziridine with indoles.
The Uses of 5-Benzyloxyindole
Reactant in regio- and stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydes Reactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditions Reactant in metal-free Friedel-Crafts alkylation reactions Reactant in preparation of protein kinase (PKC) inhibitors Reactant in preparation of indole/quinoline carbothioic acid amide derivatives.
The Uses of 5-Benzyloxyindole
- Reactant in regio- and stereoselective morpholine-catalyzed direct C-3 alkenylation with α,β-unsaturated aldehydes
- Reactant in selective debenzylation of protective groups using SiliaCat-palladium under mild reaction conditions
- Reactant in metal-free Friedel-Crafts alkylation reactions
- Reactant in preparation of protein kinase (PKC) inhibitors
- Reactant in preparation of indole/quinoline carbothioic acid amide derivatives
Purification Methods
It is recrystallised from *C6H6/pet ether or pet ether. The picrate forms red crystals from *C6H6 and has m 142-143o. [Burton & Leong Chem Ind (London) 1035 1953, Ek & Witkop J Am Chem Soc 76 5579 1954, fluorescence: Bridges & Williams Biochem J 107 225 1968, Beilstein 27 III/IV 1758.]
Properties of 5-Benzyloxyindole
| Melting point: | 100-104 °C (lit.) |
| Boiling point: | 364.56°C (rough estimate) |
| Density | 1.0707 (rough estimate) |
| refractive index | 1.5500 (estimate) |
| storage temp. | 2-8°C |
| solubility | ethanol: may be hazy yellow |
| pka | 16.63±0.30(Predicted) |
| form | powder |
| color | white to light yellow |
| BRN | 173532 |
| Exposure limits | ACGIH: TWA 20 ppm OSHA: Ceiling 300 ppm; TWA 200 ppm NIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3) |
| CAS DataBase Reference | 1215-59-4(CAS DataBase Reference) |
| NIST Chemistry Reference | 1H-indole, 5-(phenylmethoxy)-(1215-59-4) |
Safety information for 5-Benzyloxyindole
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07  Health Hazard GHS08 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H333:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H361:Reproductive toxicity |
| Precautionary Statement Codes |
P201:Obtain special instructions before use. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for 5-Benzyloxyindole
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