262439

2-Methylindole-3-carboxaldehyde

97%

• Synonym(s): 3-Formyl-2-methylindole, NSC 11895
• Empirical Formula (Hill Notation): C₁₀H₉NO
• CAS Number: 5416-80-8
• Molecular Weight: 159.18
• EC Number: 226-512-6
• MDL number: MFCD00012077
• UNSPSC Code: 12352100
• PubChem Substance ID: 24855741
• NACRES: NA.22

Properties

• Quality Level: 100
• 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

Description

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• 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