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563838

Sigma-Aldrich

5-Iodoindole

97%

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Empirical Formula (Hill Notation):
C8H6IN
CAS Number:
Molecular Weight:
243.04
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificates of Analysis (COA)

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?The synthesis of 5-iodotryptophan and some derivatives"
Harvey GD
Journal of the Chemical Society, 3760-3762 (1958)
?Convenient synthesis of 5-iodoindole?
Hydorn.EA
The Journal of Organic Chemistry, 32(12), 4100-4101 (1967)
Yoshimitsu Masuda et al.
Applied and environmental microbiology, 86(16) (2020-06-07)
YafQ is an endoribonuclease toxin that degrades target gene transcripts such as that of tnaA, a gene encoding tryptophanase to synthesize indole from tryptophan. DinJ is the cognate antitoxin of YafQ, and the YafQ-DinJ system was reported to regulate persister

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