6-Benzyloxyindole Chemical Properties

Melting point:

116-119°C

Boiling point:

411.6±20.0 °C(Predicted)

Density 

1.196±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Diethyl Ether (Slightly), Ethanol (Slightly), Ethyl Aceta

pka

17.17±0.30(Predicted)

form 

crystalline

color 

yellow to brown

BRN 

173319

InChI

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

InChIKey

FPMICYBCFBLGOZ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

15903-94-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37/39-26

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HS Code 

29339990

MSDS

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

6-Benzyloxyindole Usage And Synthesis

Chemical Properties

Colourless Crystalline Solid

Uses

Indole derivative, as antiviral and antitumor agent

Uses

• Reactant for enantioselective synthesis of quaternary carbon-containing 3-(3-indolyl)isoindolin-1-ones
• Reactant for Friedel-Crafts alkylation reactions with hydroxyisoindolinones
• Reactant for direct and regioselective synthesis of β-heteroarylated ketones
• Reactant for preparation of hepatitis C virus (HCV) inhibitors
• Reactant for preparation of protein kinase C (PKC) inhibitors
• Reactant for preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands

Synthesis

The compound (CAS: 153805-86-8) was used as starting material and synthesized by a method similar to Example 32. The specific operation was as follows: 5% rhodium/carbon powder was added to the reaction system as a catalyst, and the metal compounds ferrous acetate (II), nickel nitrate (II) or cobalt acetylacetonate (III) were introduced as co-catalysts. 5-Benzyloxy-2-(2-pyrrolidinylvinyl)nitrobenzene was used as the substrate for the reduction reaction. Upon completion of the reaction, as shown in Table 6, the yield of 6-benzyloxyindole was significantly increased and the by-product yield of 6-hydroxyindole was decreased when the reducing agent of the present invention was used as compared to the counterpart 5.

References

[1] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 39-40
[2] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 39-40
[3] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 39-40
[4] Patent: EP1541582, 2005, A1. Location in patent: Page/Page column 39-40
[5] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1178 - 1183

6-Benzyloxyindole(15903-94-3)Related Product Information

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