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543322

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
NACRES:
NA.22
PubChem Substance ID:
24878676
UNSPSC Code:
12352100
MDL number:
MFCD00435481
Assay:
97%
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assay

97%

mp

249-253 °C (lit.)

functional group

aldehyde, phenyl

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKBT0350V
14109JH
17629LI

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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)
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Global Trade Item Number

SKUGTIN
543322-5G04061832841816