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377104 Sigma-Aldrich

1-Acetylindole

98%

Synonym: NSC 521758

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Properties

Related Categories Building Blocks, C10, Chemical Synthesis, Heterocyclic Building Blocks, Indoles More...
assay   98%
refractive index   n20/D 1.607 (lit.)
bp   123-125 °C/8 mmHg (lit.)
density   1.387 g/mL at 25 °C (lit.)
storage temp.   2-8°C
SMILES string   CC(=O)n1ccc2ccccc12
InChI   1S/C10H9NO/c1-8(12)11-7-6-9-4-2-3-5-10(9)11/h2-7H,1H3
InChI key   UUCUQJHYUPXDHN-UHFFFAOYSA-N

Description

General description

Quantum chemical calculations of ground state energy, geometrical structure and vibrational wavenumbers of 1-acetylindole has been carried out using density functional (DFT/B3LYP) method. Regioselective acylations of 1-acetylindole (N-acetylindole) under Friedel-Crafts reaction has been reported. Reaction of 1-acetylindole with manganese(III) acetate in the presence of malonic acid, is reported to afford 4-acetyl-3,3a,4,8b-tetrahydro-2H-furo[3,2-b]indol-2-one.

Application

1-Acetylindole may be used in the stereocontrolled synthesis of (±)-geissoschizine. It may be used in the preparation of (1-acetyl-κO-indolyl-κC2)tetracarbonylmanganese, via a standard cyclomanganation procedure.

Reactant for preparation of:
• Antimycobacterial agents
• Cyclin-dependent kinase (CDK2) inhibitors

Reactant for:
• C3-C3 oxidative cross-coupling reactions

Packaging

1, 5 g in glass bottle

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 377104.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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