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Merck
CN

262439

2-Methylindole-3-carboxaldehyde

97%

Synonym(s):

3-Formyl-2-methylindole, NSC 11895

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About This Item

Empirical Formula (Hill Notation):
C10H9NO
CAS Number:
Molecular Weight:
159.18
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
226-512-6
MDL number:
Assay:
97%
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Quality Segment

assay

97%

mp

200-201 °C (lit.)

functional group

aldehyde

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

2-Methylindole-3-carboxaldehyde has been used in the preparation of 1-phenylsulfonyl-2-methylindole-3-carboxaldehyde.
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


pictograms

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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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable



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