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M14943

Sigma-Aldrich

5-Methoxyindole-3-carboxaldehyde

≥99%

Synonym(s):

3-Formyl-5-methoxyindole, NSC 521754

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About This Item

Empirical Formula (Hill Notation):
C10H9NO2
CAS Number:
10601-19-1
Molecular Weight:
175.18
Beilstein:
132769
EC Number:
234-220-5
MDL number:
MFCD00005623
UNSPSC Code:
12352100
PubChem Substance ID:
24896652
NACRES:
NA.22

Assay

≥99%

mp

179-183 °C (lit.)

SMILES string

COc1ccc2[nH]cc(C=O)c2c1

InChI

1S/C10H9NO2/c1-13-8-2-3-10-9(4-8)7(6-12)5-11-10/h2-6,11H,1H3

InChI key

TUWARWGEOHQXCO-UHFFFAOYSA-N

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Application

  • reactant in synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators
  • reactant in preparation of inhibitor of the C-terminal domain of RNA polymerase II
  • reactant in preparation of imidazopyridines and imidazobenzothiazoles
  • reactant in preparation of fluorescent neuroactive probes for brain imaging
  • reactant in preparation of antibacterial agents
  • reactant in synthesis of antiandrogens

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

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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Investigational new drugs, 28(3), 291-298 (2009-04-25)
A crucial event in prostate cancer progression is the transition from a hormone-sensitive to a lethal castration-refractory disease state. The antagonist-to-agonist conversion due to mutation in AR is a critical problem with the current clinically used antiandrogens. We aim to
Taleb H Al-Tel et al.
European journal of medicinal chemistry, 46(5), 1874-1881 (2011-03-19)
New antimicrobial agents, imidazo[1,2-a]pyridine and imidazo[2,1-b][1,3]benzothiazole, have been synthesized. Their antimicrobial activities were conducted against various Gram-positive, Gram-negative bacteria and fungi. Compounds 6c, 7a, 10b, 11a, 12b, 14a, 14b, 15a and 15b, exerted strong inhibition of the investigated bacterial and
Anas J M Rasras et al.
European journal of medicinal chemistry, 45(6), 2307-2313 (2010-02-26)
Synthesis and antimicrobial activity of cholic acid analogues 4a-t are reported. The synthesis of 4a-t was accomplished from ethylcholate 2. The hydrazone moiety was introduced via coupling of the cholic acid hydrazide (3) with appropriately functionalized aldehyde utilizing acetic acid
Shuhong Wu et al.
Journal of medicinal chemistry, 54(8), 2668-2679 (2011-03-30)
To optimize the antitumor activity of oncrasin-1, a small molecule RNA polymerase II inhibitor, we evaluated 69 oncrasin-1 analogues for their cytotoxic activity against normal human epithelial cells and K-Ras mutant tumor cells. About 40 of those compounds were as
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