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632422

Sigma-Aldrich

Indole-4-carboxaldehyde

97%

Synonym(s):

4-Formylindole, NSC 337264

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About This Item

Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
1074-86-8
Molecular Weight:
145.16
MDL number:
MFCD01632221
UNSPSC Code:
12352100
PubChem Substance ID:
24882325

Assay

97%

form

solid

mp

139-143 °C (lit.)

SMILES string

O=Cc1cccc2[nH]ccc12

InChI

1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H

InChI key

JFDDFGLNZWNJTK-UHFFFAOYSA-N

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General description

Indole-4-carboxaldehyde participates in the synthesis of arcyriacyanin A. Synthesis of 4-indole-4-carboxaldehyde has been reported. Intramolecular Friedel-Crafts (FC) acylation of indole-4-carboxaldehyde has been reported.

Application

  • reactant in Biginelli reaction
  • reactant in synthesis of aurora kinase A inhibitors
  • reactant in preparation of antitumor agents
  • reactant in intramolecular Friedel-Crafts acylation
  • reactant in preparation of inhibitors of cell division in E. coli
  • reactant in synthesis of Hantzsch pyridine-containing Schiff bases

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1

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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Synthesis of Fused 4, 5-Disubstituted Indole Ring Systems by Intramolecular Friedel-Crafts Acylation of 4-Substituted Indoles.
Fillion E and Dumas AM.
The Journal of Organic Chemistry, 73(7), 2920-2923 (2008)
George A Kraus et al.
Organic letters, 10(14), 3061-3063 (2008-06-25)
The reaction of (2-aminobenzyl) triphenylphosphonium bromide with aromatic aldehydes or alpha,beta-unsaturated aldehydes under microwave-assisted conditions constitutes a new synthesis of 2-substituted indoles in high yields (81-97%) in a one-pot reaction. The adduct from indole-4-carboxaldehyde was an advanced intermediate in the
Synthesis of (-)-chanoclavine I.
Kardos N and Genet J-P.
Tetrahedron Asymmetry, 5(8), 1525-1533 (1994)
Total syntheses of clavine alkaloids by an intramolecular nitrone-olefin cycloaddition reaction.
Oppolzer W, et al.
Tetrahedron, 39(22), 3695-3705 (1983)
A New Synthesis method of indole-4-carboxaldehyde.
Wu Y-M, et al.
He Cheng Hua Xue / Chinese Journal of Synthetic Chemistry, 12, 333-335 (2004)
View All Related Papers

Articles

Friedel–Crafts Acylation

Friedel-Crafts acylation with Lewis acid catalysts forms monoacylated products via electrophilic aromatic substitution of arenes.

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