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Sigma-Aldrich

5-Iodoindole

97%

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About This Item

Fórmula empírica (notación de Hill):
C8H6IN
Número de CAS:
16066-91-4
Peso molecular:
243.04
MDL number:
MFCD00220065
UNSPSC Code:
12352100
PubChem Substance ID:
24880134
NACRES:
NA.22

assay

97%

mp

101-104 °C (lit.)

SMILES string

Ic1ccc2[nH]ccc2c1

InChI

1S/C8H6IN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-5,10H

InChI key

TVQLYTUWUQMGMP-UHFFFAOYSA-N

General description

5-Iodoindole can be synthesized via nitration of m-toluidine.

Application

5-Iodoindole (5-iodogramine) may be used in the synthesis of the following:
  • 3-dimethylaminomethyl-5-iodoindole via reaction with dimethyl amine and formaldehyde
  • 5-ethynyl-1H-indole obtained via refluxing with trimethylsilylacetylene in the presence of triethylamine, catalyzed by palladium and copper(I)iodide in acetonitrile
  • 5-(3-hydroxyprop-1-enyl)-1H-indole via reaction with allyl alcohol in the presence of triphenyl phosphine, palladium acetate and silver acetate in dimethylformamide
  • 5-(3-benzyloxyprop-1-enyl)-1H-indole via reaction with allylbenzyl ether in the presence of triphenyl phosphine, palladium acetate and silver acetate in dimethylformamide
  • 5-(2-phenylethynyl)-1H-indole via refluxing with phenylacetylene catalyzed by copper(I)iodide and palladium in the presence of triethylamine in acetonitrile

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Henon H, et al.
Bioorganic & Medicinal Chemistry, 14(11), 3825-3834 (2006)
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Multi-drug resistance in nematodes is a serious problem as lately several resistant phenotypes have emerged following the intermittent usage of synthetic nematicides. Contemporary research continues to focus on developing and/or repurposing small molecule inhibitors that are eco-friendly. Here, we describe
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The subpopulation of bacterial cells that survive myriad stress conditions (e.g., nutrient deprivation and antimicrobials) by ceasing metabolism, revive by activating ribosomes. These resuscitated cells can reconstitute infections; hence, it is imperative to discover compounds which eradicate persister cells. By
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