246212
4-Benzyloxyindole
98%
Synonym(s):
NSC 92539
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About This Item
Empirical Formula (Hill Notation):
C15H13NO
CAS Number:
Molecular Weight:
223.27
UNSPSC Code:
12352100
PubChem Substance ID:
EC Number:
243-690-0
MDL number:
Assay:
98%
InChI key
LJFVSIDBFJPKLD-UHFFFAOYSA-N
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
SMILES string
C(Oc1cccc2[nH]ccc12)c3ccccc3
assay
98%
mp
57-61 °C (lit.)
functional group
phenyl
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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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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