B27803
5-(Benzyloxy)indole
95%
Synonym(s):
NSC 62895
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About This Item
Empirical Formula (Hill Notation):
C15H13NO
CAS Number:
Molecular Weight:
223.27
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
173532
Product Name
5-(Benzyloxy)indole, 95%
InChI
1S/C15H13NO/c1-2-4-12(5-3-1)11-17-14-6-7-15-13(10-14)8-9-16-15/h1-10,16H,11H2
SMILES string
C(Oc1ccc2[nH]ccc2c1)c3ccccc3
InChI key
JCQLPDZCNSVBMS-UHFFFAOYSA-N
assay
95%
form
powder
impurities
5% various solvents of crystallization
mp
100-104 °C (lit.)
Quality Level
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Application
- 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
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Jeff DeFalco et al.
Bioorganic & medicinal chemistry letters, 20(23), 7076-7079 (2010-10-23)
5-Benzyloxytryptamine 19 was found to act as an antagonist of the TRPM8 ion-channel. For example, 19 had an IC(50) of 0.34 μM when menthol was used as the stimulating agonist. Related commercially-available tryptamine derivatives showed diminished, or no antagonist activity
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