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B27803

Sigma-Aldrich

5-(Benzyloxy)indole

95%

Synonym(s):

NSC 62895

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About This Item

Empirical Formula (Hill Notation):
C15H13NO
CAS Number:
1215-59-4
Molecular Weight:
223.27
Beilstein:
173532
MDL number:
MFCD00005676
UNSPSC Code:
12352100
PubChem Substance ID:
24891673
NACRES:
NA.22

Assay

95%

form

powder

impurities

5% various solvents of crystallization

mp

100-104 °C (lit.)

SMILES string

C(Oc1ccc2[nH]ccc2c1)c3ccccc3

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

InChI key

JCQLPDZCNSVBMS-UHFFFAOYSA-N

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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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