3-formyl-1H-indole-5-carbonitrile

• ChemBase ID: 66302
• Molecular Formular: C10H6N2O
• Molecular Mass: 170.16744
• Monoisotopic Mass: 170.04801282
• SMILES: [nH]1cc(c2cc(ccc12)C#N)C=O
• Canonical SMILES: O=Cc1c[nH]c2c1cc(C#N)cc2
• InChI: InChI=1S/C10H6N2O/c11-4-7-1-2-10-9(3-7)8(6-13)5-12-10/h1-3,5-6,12H
• InChIKey: NVBCFOQYDFKXJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-formyl-1H-indole-5-carbonitrile
• IUPAC Traditional name: 3-formyl-1H-indole-5-carbonitrile
• Synonyms: 3-formyl-1H-indole-5-carbonitrile; 5-Cyanoindole-3-carboxyaldehyde; 5-Cyano-1H-indole-3-carboxaldehyde 98%; 5-Cyanoindole-3-carboxaldehyde; 3-Formyl-5-cyano-1H-indole; 3-Formyl-1H-indole-5-carbonitrile; 3-甲酰-5-氰基-1H-吲哚; 5-氰基吲哚-3-甲醛

Database IDs

• CAS Number: 17380-18-6
• MDL Number: MFCD01719101
• PubChem SID: 162032040
• PubChem CID: 28504

CALCULATED PROPERTIES

• Acid pKa: 13.235175
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.6406063
• LogD (pH = 7.4): 1.6406057
• Log P: 1.6406063
• Molar Refractivity: 49.4501 cm^3
• Polarizability: 19.275892 Å^3
• Polar Surface Area: 56.65 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 239 - 241°C; 248-253 °C
• Hydrophobicity(logP): 1.583

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-43
• Safety Statements: 26-36/37
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H317-H319-H332-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+%; 97%
• Empirical Formula (Hill Notation): C10H6N2O

DETAILS

Sigma Aldrich - 701327

Packaging
1, 5 g in glass bottle
Application

• Reactant for synthesis of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators1
• Reactant for enantioselective preparation of antifungal agents2
• Reactant for synthesis of indole- and 7-azaindole-1,3-dicarboxamide hydroxyethylamine inhibitors of BACE-13
• Reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents4
• Reactant for preparation of indolecarboxamide derivatives as antitumor agents5
• Reactant for synthesis of a selective serotonin reuptake inhibitor6