Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

691534

Sigma-Aldrich

4-Nitroindole-3-carboxaldehyde

97%

Synonym(s):

3-Formyl-4-nitroindole

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C9H6N2O3
CAS Number:
10553-11-4
Molecular Weight:
190.16
MDL number:
MFCD04973979
UNSPSC Code:
12352100
PubChem Substance ID:
329761416
NACRES:
NA.22

assay

97%

form

solid

mp

189-193 °C

functional group

aldehyde
nitro

SMILES string

[O-][N+](=O)c1cccc2[nH]cc(C=O)c12

InChI

1S/C9H6N2O3/c12-5-6-4-10-7-2-1-3-8(9(6)7)11(13)14/h1-5,10H

InChI key

CGXVTWQTGQAMMX-UHFFFAOYSA-N

Application

  • reactant in synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators
  • reactant in synthesis of structural analogs of thaxtomin
  • reactant in preparation of chromophores related to gold fluorescent protein
  • reactant in preparation of brassinin and gramine derivatives

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - 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, Faceshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
07605LH

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Yamada, F.; et al.
Heterocycles, 36, 2783-2783 (1993)
Molesworth, P., P.; et al.
Australian Journal of Chemistry, 63, 813-813 (2010)
Tetrahedron, 46, 6085-6085 (1990)
Prueger, Birgit; Bach, Thorsten.
Synthesis, 7, 1103-1103 (2007)
Eduard Dolusić et al.
Journal of medicinal chemistry, 54(15), 5320-5334 (2011-07-06)
Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active area of research in drug development. Recently, our group has shown that tryptophan 2,3-dioxygenase

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