1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

• ChemBase ID: 36147
• Molecular Formular: C8H6N2O
• Molecular Mass: 146.14604
• Monoisotopic Mass: 146.04801282
• SMILES: [nH]1c2c(c(c1)C=O)cccn2
• Canonical SMILES: O=Cc1c[nH]c2c1cccn2
• InChI: InChI=1S/C8H6N2O/c11-5-6-4-10-8-7(6)2-1-3-9-8/h1-5H,(H,9,10)
• InChIKey: KAIWRKYDYWYFIT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
• IUPAC Traditional name: 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde
• Synonyms: 1H-Pyrrolo[2,3-b]pyridine-3-carboxaldehyde; 3-Formyl-1H-pyrrolo[2,3-b]pyridine; 7-Azaindole-3-carboxaldehyde; 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde; 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde; 7-Azaindole-3-carboxaldehyde; 1H-吡咯并[2,3-b]吡啶-3-甲醛; 7-氮杂吲哚-3-甲醛

Database IDs

• CAS Number: 4649-09-6
• MDL Number: MFCD03407363
• PubChem SID: 160999454
• PubChem CID: 5372812

CALCULATED PROPERTIES

• Acid pKa: 12.890143
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.9261067
• LogD (pH = 7.4): 0.934194
• Log P: 0.93429977
• Molar Refractivity: 41.5242 cm^3
• Polarizability: 15.87386 Å^3
• Polar Surface Area: 45.75 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 211 - 213°C; 214 - 216 °C; 216-220 °C; 216-220°C
• Hydrophobicity(logP): 1.027

Safety Information

• Storage Warning: Harmful/Irritant; IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38-43
• Safety Statements: 26-36/37
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H317-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: >95%; 95%; 95+%; 97%
• Empirical Formula (Hill Notation): C8H6N2O
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 694681

Application
Useful starter in 7-azaindole chemistry9,10,11
Reactant for preparation of:
• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1
• Inhibitors of BACE-1 activity2
• Prostate cancer invasion and migration inhibitors3
• CDK2 kinase inhibitors4
• Cell division cycle 7 kinase inhibitors5
• Inhibitor of oncogenic B-Raf kinase with potent antimelanoma activity6
• Antidiabetic agents7
• Inhibitors of brassinin glucosyltransferase8
Packaging
1 g in glass bottle