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563838 Sigma-Aldrich

5-Iodoindole

97%

  • CAS Number 16066-91-4

  • Empirical Formula (Hill Notation) C8H6IN

  • Molecular Weight 243.04

  •  MDL number MFCD00220065

  •  PubChem Substance ID 24880134

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Halogenated Heterocycles, Heterocyclic Building Blocks,
Quality Level   100
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

Description

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

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Indoles

Sigma-Aldrich is proud to offer a new series of ChemFiles—called Privileged Structures, to our Drug Discovery and Organic Synthesis customers. Each piece will highlight a specific motif, selected app...
Chemfiles Volume 4 Article 8
Keywords: Building blocks, Cardiovascular, Diabetes, Diseases, Drug discovery, Medicinal chemistry, Organic synthesis, Respiratory

Peer-Reviewed Papers
15

References

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