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: 2026-05-27 22:52:20

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.