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543322

Sigma-Aldrich

2-Phenylindole-3-carboxaldehyde

97%

Synonym(s):

3-Formyl-2-phenylindole

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About This Item

Empirical Formula (Hill Notation):
C15H11NO
CAS Number:
25365-71-3
Molecular Weight:
221.25
MDL number:
MFCD00435481
UNSPSC Code:
12352100
PubChem Substance ID:
24878676
NACRES:
NA.22

Assay

97%

mp

249-253 °C (lit.)

SMILES string

O=Cc1c([nH]c2ccccc12)-c3ccccc3

InChI

1S/C15H11NO/c17-10-13-12-8-4-5-9-14(12)16-15(13)11-6-2-1-3-7-11/h1-10,16H

InChI key

IFIFXODAHZPTEY-UHFFFAOYSA-N

Application

2-Phenylindole-3-carboxaldehyde may be used to synthesize:
  • 2-phenylindole-3-carboxaldehyde oxime
  • 2-phenyl-1H-indole-3-carboxaldehyde O-methyl oxime
  • 2-phenylindole-3-carbonitrile
Reactant for preparation of:
  • Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
  • Pyrimidinones via Biginelli reaction as antimicrobial agents
  • [(phenyl)pyrazolyl]indole derivatives as antiinflammatory agents and analgesics
  • Indole thiophene chalcones via Claisen-Schmidt condensation as antimicrobial and antioxidant agents
  • Benzofuranone attached indole derivatives as PI3K inhibitors
  • Ionone-based chalcones as novel antiandrogens
  • Oxazolylindoles as antiinflammatory agents for edema

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Novel indium-mediated ternary reactions between indole-3-carboxaldehydes-allyl bromide-enamines: facile synthesis of bisindolyl-and indolyl-heterocyclic alkanes.
Kumar S, et al.
Tetrahedron Letters, 44(10), 2101-2104 (2003)
Xufen Yu et al.
Organic & biomolecular chemistry, 10(44), 8835-8847 (2012-10-10)
Development of small molecule drug-like inhibitors blocking both nitric oxide synthase and NFκB could offer a synergistic therapeutic approach in the prevention and treatment of inflammation and cancer. During the course of evaluating the biological potential of a commercial compound
Iridium-catalyzed regio- and enantioselective N-allylation of indoles.
Levi M Stanley et al.
Angewandte Chemie (International ed. in English), 48(42), 7841-7844 (2009-09-18)
Acylation of indoles by Duff reaction and Vilsmeier-Haack formylation and conformation of N-formylindoles.
Chatterjee A and Biswas KM.
The Journal of Organic Chemistry, 38(23), 4002-4004 (1973)

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