2,2,2-trifluoro-1-(1H-indol-3-yl)ethan-1-one

• ChemBase ID: 41692
• Molecular Formular: C10H6F3NO
• Molecular Mass: 213.1559496
• Monoisotopic Mass: 213.04014848
• SMILES: c1(C(=O)C(F)(F)F)c[nH]c2c1cccc2
• Canonical SMILES: O=C(C(F)(F)F)c1c[nH]c2c1cccc2
• InChI: InChI=1S/C10H6F3NO/c11-10(12,13)9(15)7-5-14-8-4-2-1-3-6(7)8/h1-5,14H
• InChIKey: LCMDCXWSHDFQKP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2,2-trifluoro-1-(1H-indol-3-yl)ethan-1-one
• IUPAC Traditional name: INDOLE3trifluoroacetyl
• Synonyms: 2,2,2-Trifluoro-1-(1H-indol-3-yl)-1-ethanone; 3-Indolyl trifluoromethyl ketone; 3-(Trifluoroacetyl)indole; 3-(三氟乙酰基)吲哚

Database IDs

• CAS Number: 14618-45-2
• MDL Number: MFCD00182114
• PubChem SID: 24866420; 162046455
• PubChem CID: 589126

CALCULATED PROPERTIES

• Acid pKa: 12.061388
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.7619839
• LogD (pH = 7.4): 2.7619748
• Log P: 2.7619839
• Molar Refractivity: 48.5575 cm^3
• Polarizability: 18.503904 Å^3
• Polar Surface Area: 32.86 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 211-214 °C(lit.); 218 - 220 °C; 218-220°C

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: >95%; 99%
• Empirical Formula (Hill Notation): C10H6F3NO

DETAILS

Sigma Aldrich - 422223

Packaging
1, 5 g in glass bottle
Application

• Reactant for enantioselective synthesis of indoles via palladium-catalyzed kinetic asymmetrical alkylation1
• Reactant for preparation of N-pyridinyl indolecarboxamides via amidation of aminopyridine derivatives. with indolecarboxylic acid2
• Reactant for preparation of mast cell tryptase inhibitors, starting from indoles; using amidation as the key step3
• Reactant for formation of Michael adducts via Baylis-Hillman reaction4
• Reactant for preparation of indolecarboxamides via haloform cleavage of (trifluoroacetyl)indole with lithium dialkylamides5