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357839 Aldrich

1,5,6,7-Tetrahydro-4H-indol-4-one

98%

Synonym: 4,5,6,7-Tetrahydro-4-oxoindole, NSC 131681

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Properties

Related Categories Building Blocks, C7 to C9, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
InChI Key   KASJZXHXXNEULX-UHFFFAOYSA-N
assay   98%
mp   188-190 °C(lit.)

Description

Packaging

5 g in glass bottle

Application

• Reactant in synthesis of psammopemmin A as antitumor agent
• Reactant in synthesis of a 1,3,4,5-tetrahydrobenzindole β-ketoesters and tricyclic tetrahydrobenzindoles via C-H insertion reactions
• Reactant in preparation of tricyclic indole and dihydroindole derivatives as inhibitors of guanylate cyclase
• Reactant in preparation of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of (halobenzyl)pyrroles
• Reactant in enantioselective preparation of arylalkenyl indoles via asymmetric C-H insertion of rhodium carbenoids followed by Cope rearrangement-elimination

1,5,6,7-Tetrahydro-4H-indol-4-one may be used in the preparation of:
• 4-oxo-4,5,6,7-tetrahydro-1H-indole-2-carbonitrile
• methyl 2-(4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)acrylate
• 3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-1-yl)propanenitrile
• potent and orally active 5-HT1A agonists, (R)-(+)- and (S)-(-)-1-formyl-6,7,8,9-tetrahydro-N,N-dipropyl-3H-benz[e]indol-8-amines

General description

Iodination of 1,5,6,7-tetrahydro-4H-indol-4-one using 1-chloromethyl­-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetra­fluoroborate) yields α-iodo derivative as the main product.

Price and Availability

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
Protocols & Articles
Peer-Reviewed Papers
15

References

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