4-Benzyloxyindole Chemical Properties

Melting point:

57-61 °C (lit.)

Boiling point:

364.56°C (rough estimate)

Density 

1.0707 (rough estimate)

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

17.17±0.30(Predicted)

form 

Solid

color 

Beige to Brown

BRN 

183150

InChI

InChI=1S/C15H13NO/c1-2-5-12(6-3-1)11-17-15-8-4-7-14-13(15)9-10-16-14/h1-10,16H,11H2

InChIKey

LJFVSIDBFJPKLD-UHFFFAOYSA-N

SMILES

N1C2=C(C(OCC3=CC=CC=C3)=CC=C2)C=C1

CAS DataBase Reference

20289-26-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Benzyloxyindole Usage And Synthesis

Chemical Properties

Off-White Crystalline Solid with Few Darker (Brown) Particles

Uses

Indole derivative as substrate-binding; N297Q and I300V mutants of cytochrome P 450 2A6 display expansion of substrate specificity of cytochrome P 450 2A6 to oxidize substituted indoles

Uses

4-Benzyloxyindole was used in the synthesis of 4-alkyloxy-aminoalkyl indole derivatives.

Reactions

4-Benzyloxyindole was used in the synthesis of 4-alkyloxy-aminoalkyl indole derivatives.

1. Reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition
2. Reactant for preparation of indoles by Bartoli reductive cyclization as useful intermediates in medicinal chemistry research
3. Reactant for synthesis of carbon-11-labeled 4-aryl-4H-chromenes as new PET agents for imaging of apoptosis in cancer
4. Reactant for preparation of HCV inhibitors.
5. Reactant for preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands
6. Reactant for preparation of 4-aryl-4H-chromenes as apoptosis inducers

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 34, 1990
The Journal of Organic Chemistry, 51, p. 4294, 1986 DOI: 10.1021/jo00372a037
Tetrahedron Letters, 24, p. 4561, 1983 DOI: 10.1016/S0040-4039(00)85955-9

Synthesis

To a stirred solution of 162.2 g (0.50 mol) of (E)-6-benzyloxy-2-nitro-β-pyrrolidinostyrene in 1 L of THF and 1 L of methanol at 30°C under nitrogen is added 10 mL of Raney nickel followed by 44 mL (0.75 mol) of 85% hydrazine hydrate. Vigorous gas evolution is observed. The red color turns dark brown within 10 minutes, and the reaction temperature rises to 46°C. An additional 44 mL of 85% hydrazine hydrate is added after 30 min and again 1 hr later. The temperature is maintained between 45 and 50°C with a water bath during the reaction and for 2 hr after the last addition. The mixture is cooled to room temperature, and the catalyst is removed by filtration through a bed of Celite. The catalyst is washed several times with methylene chloride. The filtrate is evaporated, and the residue is dried by evaporating with 500 mL of toluene. The reddish residue (118.5 g), dissolved in ca. 1 L of toluene-cyclohexane (1 : 1), is applied to a column of 500 g of silica gel (70–230-mesh, Merck) prepared in the same solvent. Elution with 6.0 L of toluene–cyclohexane (1 : 1) followed by 3 L of toluene–cyclohexane (1 : 2) affords 108.3 g of white solid, which is crystallized from 150 mL of toluene and 480 mL of cyclohexane. 107.3 g (96% yield) of 4-benzyloxyindole is obtained in three crops as white prisms, mp 60–62°C.

4-Benzyloxyindole(20289-26-3)Related Product Information

• Indole-3-acetic acid
• Indometacin
• Indole
• Indole-3-butyric acid
• 4-Methoxybenzylchloride
• 2-CARBETHOXY-4-BENZYLOXYINDOLE
• 5-Benzyloxyindole
• 4-Benzyloxyindole-3-carboxaldehyde 98%
• N-BOC-4-BENZYLOXYINDOLE-2-BORONIC ACID,4-Benzyloxyindole-2-boronic acid, N-BOC protected 98%,4-Benzyloxyindole-2-boronic acid, N-BOC protected
• ETHYL 5-BENZYLOXYINDOLE-3-GLYOXYLATE
• 7-BENZYLOXYINDOLE 98+%,7-Benzyloxyindole 98%
• 5-BENZYLOXYINDOLE-2-CARBOXYLIC ACID
• 3-(2-AMINOETHYL)-5-BENZYLOXYINDOLE
• ETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATE
• 4-BENZYLOXYINDOLE
• 4-BENZYLOXY-3-INDOLEACETONITRILE
• 5-BENZYLOXYINDOLE-3-ACETIC ACID
• 6-Benzyloxyindole-2-boronic acid, N-BOC protected,6-Benzyloxyindole-2-boronic acid, N-BOC protected 98%,N-BOC-6-BENZYLOXYINDOLE-2-BORONIC ACID