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Sigma-Aldrich

5-Iodoindole

97%

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About This Item

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

Signal Word

Warning

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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?Convenient synthesis of 5-iodoindole?
Hydorn.EA
The Journal of Organic Chemistry, 32(12), 4100-4101 (1967)
"Synthesis and biological evaluation of new dipyrrolo [3, 4-a: 3, 4-c] carbazole-1, 3, 4, 6-tetraones, substituted with various saturated and unsaturated side chains via palladium catalyzed cross-coupling reactions"
Henon H, et al.
Bioorganic & Medicinal Chemistry, 14(11), 3825-3834 (2006)
Sooyeon Song et al.
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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
?The synthesis of 5-iodotryptophan and some derivatives"
Harvey GD
Journal of the Chemical Society, 3760-3762 (1958)
Satish Kumar Rajasekharan et al.
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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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