Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

513830

Sigma-Aldrich

Indole-5-carboxaldehyde

98%

Synonym(s):

5-Formylindole

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C9H7NO
CAS Number:
Molecular Weight:
145.16
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

mp

100-103 °C (lit.)

SMILES string

O=Cc1ccc2[nH]ccc2c1

InChI

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

InChI key

ADZUEEUKBYCSEY-UHFFFAOYSA-N

Application

Indole-5-carboxaldehyde can be used as a reactant in the:
  • Preparation of curcumin derivatives as anti-proliferative & anti-inflammatory agents
  • Preparation of analogs of botulinum neurotoxin serotype A protease inhibitors
  • Stereoselective synthesis of dibenzylideneacetone derivatives as β-amyloid imaging probes
  • Synthesis of para-para stilbenophanes by McMurry coupling
  • Stereoselective synthesis of heteroaromatic (E)-α,β-unsaturated ketones from aldehydes
  • Structure-based drug design of aurora kinase A inhibitors
  • Preparation of 5-indolyl linked 15- and 18-membered azacrown ethers to study their cation-π interactions.
  • Preparation of bibenzimidazole derivatives substituted 5-indolyl moiety in the study of inhibition of topoisomerase I activity.
  • Synthesis of (5-(4-(3,4,5-trimethoxybenzoyl)-1H-imidazol-2-yl)-1H-indol-2-yl)(3,4,5-trimethoxyphenyl)methanone and radioiodinated indolochalcone.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Raquel Álvarez et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(12), 3406-3419 (2011-02-24)
The synthesis of a new family of methoxy-substituted [2.7]- and [2.8]paracyclophanes linked by 3-oxapentamethylene-1,5-dioxy and hexamethylene-1,6-dioxy bridges has been carried out by using the McMurry methodology. Related indole compounds were also synthesised. Olefin-to-diol ratios depended on the bridge length, the
Balducci, E.; et al.
European Journal of Organic Chemistry, 311-311 (2011)
Houlihan WJ.
The Chemistry of Heterocyclic Compounds, 367-367 (2009)
Mohane Selvaraj Coumar et al.
Journal of medicinal chemistry, 52(4), 1050-1062 (2009-01-15)
Aurora kinases have emerged as attractive targets for the design of anticancer drugs. Through structure-based virtual screening, novel pyrazole hit 8a was identified as Aurora kinase A inhibitor (IC(50) = 15.1 microM). X-ray cocrystal structure of 8a in complex with
Petr Capek et al.
ACS chemical neuroscience, 2(6), 288-293 (2011-07-12)
Botulinum neurotoxin (BoNT), the etiological agent that causes the neuroparalytic disease botulism, has become a highly studied drug target in light of the potential abuse of this toxin as a weapon of bioterrorism. In particular, small molecule inhibitors of the

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service