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691534

Sigma-Aldrich

4-Nitroindole-3-carboxaldehyde

97%

Synonym(s):

3-Formyl-4-nitroindole

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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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - 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

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Certificates of Analysis (COA)

Lot/Batch Number
07605LH

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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)
Yamada, F.; et al.
Heterocycles, 36, 2783-2783 (1993)
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

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