908295-26-1

Basic information

• Product Name: 3-IODO-5-NITRO-1H-INDOLE
• Synonyms: 3-IODO-5-NITRO-1H-INDOLE;3-Iodo-5-nitroindole
• CAS NO: 908295-26-1
• Molecular Formula: C₈H₅IN₂O₂
• Molecular Weight: 288.04
• Mol File: 908295-26-1.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-IODO-5-NITRO-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-IODO-5-NITRO-1H-INDOLE(908295-26-1)
• EPA Substance Registry System: 3-IODO-5-NITRO-1H-INDOLE(908295-26-1)

Safety Data

• Hazardous Substances Data: 908295-26-1(Hazardous Substances Data)

Upstream product

• 6146-52-7 5-nitroindole 

Downstream Products

• 914349-32-9 tert-butyl 3-iodo-5-nitro-1H-indole-1-carboxylate 
• 1432521-32-8 3-(2-(2,2-dibromovinyl)phenyl)-5-nitro-1-tosyl-1H-indole 
• 1432521-45-3 2-(5-nitro-1-tosyl-1H-indol-3-yl)benzaldehyde 
• 1027787-68-3 3-iodo-5-nitro-1-tosyl-1H-indole 
• 611-09-6 5-nitroisatin 

Relevant articles and documents

5-Nitroindole oligonucleotides with alkynyl side chains: Universal base pairing, triple bond hydration and properties of pyrene "click" adducts

Oligonucleotides with 3-ethynyl-5-nitroindole and 3-octadiynyl-5-nitroindole 2′-deoxyribonucleosides were prepared by solid-phase synthesis. To this end, nucleoside phosphoramidites with clickable side chains were synthesized. The 3-ethynylated 5-nitroindole nucleoside was hydrated during automatized DNA synthesis to 3-acetyl-5-nitroindole 2′-deoxyribonucleoside. Side product formation was circumvented by triisopropylsilyl protection of the ethynyl side chain and was removed with TBAF after oligonucleotide synthesis. All compounds with a clickable 5-nitroindole skeleton show universal base pairing and can be functionalized with almost any azide in any position of the DNA chain. Functionalization of the side chain with 1-azidomethylpyrene afforded click adducts in which the fluorescence was quenched by the 5-nitroindole moieties. However, fluorescence was slightly recovered during duplex formation. Oligonucleotides with a pyrene residue and a long linker arm are stabilized over those with non-functionalized side chains. From the UV red shift of the pyrene residue in oligonucleotides and modelling studies, pyrene intercalation was established for the long linker adduct showing increased duplex stability over those with a short side chain. This journal is

PhI(OAc)2/NaX-mediated halogenation providing access to valuable synthons 3-haloindole derivatives

This paper describes a mild phenyliodine diacetate mediated method for selective chlorination, bromination, and iodination of indole C-H bonds using sodium halide as a source for analogous halogenations. The combination of NaX and phenyliodine diacetate provides an invincible system for halogenation of indoles. This protocol was compatible with a wide array of indole substrates and provides straight forward access to potential halogenated arenes.

Synthesis of isatins by I2/TBHP mediated oxidation of indoles

An I2/TBHP mediated oxidation of commercially available indoles has been developed, which affords isatins in moderate to good yields.