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Safety Information

422223

Sigma-Aldrich

3-(Trifluoroacetyl)indole

99%

Synonym(s):

3-Indolyl trifluoromethyl ketone

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About This Item

Empirical Formula (Hill Notation):
C10H6F3NO
CAS Number:
14618-45-2
Molecular Weight:
213.16
MDL number:
MFCD00182114
UNSPSC Code:
12352100
PubChem Substance ID:
24866420

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

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.

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

422223-1G:
422223-5G:
422223-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
1404250
1404252
07307JG
08630HG
U11538

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Synthesis of indole-3-carboxamides via a haloform cleavage reaction of 3-trifluoroacetylindole with lithium dialkylamides.
Hassinger HL, et al
Tetrahedron Letters, 39(20), 3095-3098 (1998)

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