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379492

Sigma-Aldrich

1-Acetylindoline

98%

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About This Item

Empirical Formula (Hill Notation):
C10H11NO
CAS Number:
16078-30-1
Molecular Weight:
161.20
MDL number:
MFCD00022908
UNSPSC Code:
12352100
PubChem Substance ID:
24863664
NACRES:
NA.22

assay

98%

mp

102-104 °C (lit.)

SMILES string

CC(=O)N1CCc2ccccc12

InChI

1S/C10H11NO/c1-8(12)11-7-6-9-4-2-3-5-10(9)11/h2-5H,6-7H2,1H3

InChI key

RNTCWULFNYNFGI-UHFFFAOYSA-N

General description

1-Acetylindoline, a substituted indole, is a tertiary amide having bulky N-groups. Its reduction to the corresponding amine, by reaction with silane in the presence of MoO2Cl2 (catalyst), has been reported.[1]

Application

1-Acetylindoline may be used in the synthesis of 5-chloroindole.[2]
  • Reactant for preparation of triazolothiadiazepine dioxide derivatives
  • Reactant for preparation of halo-substituted aromatic amides
  • Reactant for preparation of [[(phenyl)piperazinyl]alkyl]indolyl]ethanone and [[[(phenoxyethyl)piperazinyl]alkyl]indolyl]ethanone derivatives as α1-adrenoreceptor antagonists
  • Reactant for synthesis of naphthalenedione derivatives as antimycobacterial agents
  • Reactant for regioselective ortho Suzuki-Miyaura coupling reaction

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
03430PH
13805MN
10015MQ
13012PU
09914EY

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Reduction of amides with silanes catalyzed by MoO2Cl2.
Fernandes AC and Rom?o CC.
J. Mol. Catal. A: Chem., 272(1), 60-63 (2007)
Highly Convenient and Large Scale Synthesis of 5-chloroindole and its 3-substituted Analogues
Keetha L, et al.
J. Korean Chem. Soc., 55(2) (2011)
The synthesis of 5-and 7-acetylindole derivatives. I: The photochemical rearrangement of 1-acetylindoline.
Akagi M and Ozaki K.
Heterocycles, 26(!), 61-64 (1987)

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