5-Benzyloxyindole

5-Benzyloxyindole
  • CAS No.:1215-59-4
Other grades of this product :
5-Benzyloxyindole Basic information
Product Name:5-Benzyloxyindole
Synonyms:BENZYLOXYINDOLE(5-);5-(Phenylmethoxy)-1H-indole;5-benzyloxy-indol;Benzyloxy-5 indole;Indole, 5-(benzyloxy)-;TIMTEC-BB SBB003331;5-BENZYLOXY-1H-INDOLE;5-BENZYLOXYINDOLE
CAS:1215-59-4
MF:C15H13NO
MW:223.27
EINECS:214-930-1
Product Categories:Heterocycle-Indole series;Aromatics;Simple Indoles;Indole;Pyrroles & Indoles;Indole Derivatives;blocks;Indoles and derivatives;Pyrroles & Indoles;Indoline & Oxindole;Indole Series;Indoles;Building Blocks;Heterocyclic Building Blocks;IndolesOxindoles
Mol File:1215-59-4.mol
5-Benzyloxyindole Chemical Properties
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
form powder
pka16.63±0.30(Predicted)
color white to light yellow
BRN 173532
Exposure limitsACGIH: TWA 20 ppmOSHA: Ceiling 300 ppm; TWA 200 ppmNIOSH: IDLH 500 ppm; TWA 100 ppm(375 mg/m3); STEL 150 ppm(560 mg/m3)
CAS DataBase Reference1215-59-4(CAS DataBase Reference)
NIST Chemistry Reference1H-indole, 5-(phenylmethoxy)-(1215-59-4)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-24/25-22
WGK Germany 3
RTECS NL4850000
8-10
HazardClass IRRITANT
HS Code 29339990
MSDS Information
ProviderLanguage
5-(Benzyloxy)-1H-indole English
SigmaAldrich English
ACROS English
ALFA English
5-Benzyloxyindole Usage And Synthesis
Chemical PropertiesOff-white to beige powder
UsesReactant 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.
Uses
  • 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
Uses5-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.
Purification MethodsIt 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.]

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