563838

5-Iodoindole

97%

• Empirical Formula (Hill Notation): C₈H₆IN
• CAS Number: 16066-91-4
• Molecular Weight: 243.04
• MDL number: MFCD00220065
• UNSPSC Code: 12352100
• PubChem Substance ID: 24880134
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 97%
• mp: 101-104 °C (lit.)
• functional group: iodo
• 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

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• 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