422223

3-(Trifluoroacetyl)indole

99%

• Synonym(s): 3-Indolyl trifluoromethyl ketone
• Empirical Formula (Hill Notation): C₁₀H₆F₃NO
• CAS Number: 14618-45-2
• Molecular Weight: 213.16
• MDL number: MFCD00182114
• UNSPSC Code: 12352100
• PubChem Substance ID: 24866420

Properties

• assay: 99%
• mp: 211-214 °C (lit.)
• SMILES string: FC(F)(F)C(=O)c1c[nH]c2ccccc12
• InChI: 1S/C10H6F3NO/c11-10(12,13)9(15)7-5-14-8-4-2-1-3-6(7)8/h1-5,14H
• InChI key: LCMDCXWSHDFQKP-UHFFFAOYSA-N

Description

General description

3-(Trifluoroacetyl)indole is a heterocyclic trifluoromethyl ketone. One of the methods reported for its synthesis is by the reaction of indole with trifluoroacetic anhydride.[1]

Application

• Reactant for enantioselective synthesis of indoles via palladium-catalyzed kinetic asymmetrical alkylation
• Reactant for preparation of N-pyridinyl indolecarboxamides via amidation of aminopyridine derivatives. with indolecarboxylic acid
• Reactant for preparation of mast cell tryptase inhibitors, starting from indoles; using amidation as the key step
• Reactant for formation of Michael adducts via Baylis-Hillman reaction
• Reactant for preparation of indolecarboxamides via haloform cleavage of (trifluoroacetyl)indole with lithium dialkylamides

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