262439

Sigma-Aldrich

2-Methylindole-3-carboxaldehyde

97%

Synonym(s):
3-Formyl-2-methylindole, NSC 11895
Empirical Formula (Hill Notation):
C10H9NO
CAS Number:
Molecular Weight:
159.18
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

200-201 °C (lit.)

SMILES string

Cc1[nH]c2ccccc2c1C=O

InChI

1S/C10H9NO/c1-7-9(6-12)8-4-2-3-5-10(8)11-7/h2-6,11H,1H3

InChI key

CYZIVXOEJNAIBS-UHFFFAOYSA-N

General description

Oxidative activation of 2-methylindole-3-carboxaldehyde via N-heterocyclic carbene organocatalysis generates heterocyclic ortho-quinodimethane as a key intermediate.

Application

Reactant for preparation of:
  • Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators
  • Fluorescent sensors (BODIPY)
  • Antimicrobial agents against methicillin-resistant Staphylococcus aureus
  • G protein-coupled receptor CRTh2 antagonists
  • Inhibitors of PI3 kinase-α
  • Antitubercular agents
  • Anti-inflammatory agents
  • Mycobacterium tuberculosis protein tyrosine phosphatase B
  • Glucocorticoid receptor ligands
  • Agents stimulating neurite outgrowth
2-Methylindole-3-carboxaldehyde has been used in the preparation of 1-phenylsulfonyl-2-methylindole-3-carboxaldehyde.

Packaging

25 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

G Chakkaravarthi et al.
Acta crystallographica. Section E, Structure reports online, 64(Pt 2), o542-o542 (2008-01-01)
In the title compound, C(16)H(15)NO(3)S, the plane of the phenyl ring forms a dihedral angle of 80.37 (8)° with the indole ring system. The crystal packing is stabilized by weak O-H⋯O hydrogen bonds which link the mol-ecules into infinite chains along...
Xingkuan Chen et al.
Angewandte Chemie (International ed. in English), 52(42), 11134-11137 (2013-09-17)
Aryl aldehyde activation: Oxidative activation of 2-methylindole-3-carboxaldehyde (I) through N-heterocyclic carbene (NHC) organocatalysis generates heterocyclic ortho-quinodimethane (II) as a key intermediate. This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones or isatins to form polycyclic lactones containing a quaternary...
Ming-Zhi Zhang et al.
European journal of medicinal chemistry, 92, 776-783 (2015-01-31)
Streptochlorin, first isolated as a new antibiotic in 1988 from the lipophilic extracts of the mycelium of a Streptomyces sp, is an indole natural products with a variety of biological activities. Based on the methods developed for the synthesis of...

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