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246212

Sigma-Aldrich

4-Benzyloxyindole

98%

Synonym(s):

NSC 92539

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About This Item

Empirical Formula (Hill Notation):
C15H13NO
CAS Number:
20289-26-3
Molecular Weight:
223.27
EC Number:
243-690-0
MDL number:
MFCD00047200
UNSPSC Code:
12352100
PubChem Substance ID:
24854794

Assay

98%

mp

57-61 °C (lit.)

SMILES string

C(Oc1cccc2[nH]ccc12)c3ccccc3

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

InChI key

LJFVSIDBFJPKLD-UHFFFAOYSA-N

Application

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A K Dutta et al.
Bioorganic & medicinal chemistry, 5(8), 1591-1600 (1997-08-01)
Several novel 4-alkyloxy-aminoalkyl indole derivatives 3 were synthesized from 4-benzyloxyindole (1). Alkylation of 1 with 4-(2-chloroethyl)morpholine (NaH/HMPA) formed 2. Deprotection using palladium hydroxide on carbon/hydrogen followed by alkylation with the appropriate alkyl bromide gave the target compounds 3b-3j. In the
Ruinan Yang et al.
The Journal of pharmacology and experimental therapeutics, 370(3), 864-875 (2019-04-19)
Castration-resistant prostate cancer that has become resistant to docetaxel (DTX) represents one of the greatest clinical challenges in the management of this malignancy. There is an urgent need to develop novel therapeutic agents to overcome chemoresistance and improve the overall

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