1H-indole-4-carbonitrile

• ChemBase ID: 12049
• Molecular Formular: C9H6N2
• Molecular Mass: 142.15734
• Monoisotopic Mass: 142.0530982
• SMILES: N#Cc1cccc2[nH]ccc12
• Canonical SMILES: N#Cc1cccc2c1cc[nH]2
• InChI: InChI=1S/C9H6N2/c10-6-7-2-1-3-9-8(7)4-5-11-9/h1-5,11H
• InChIKey: CEUFGDDOMXCXFW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indole-4-carbonitrile
• IUPAC Traditional name: indole-4-cyano-
• Synonyms: 4-Cyanoindole; 4-Cyano-1H-indole; 1H-Indole-4-carbonitrile; Indole-4-carbonitrile; 4-Cyanoindole; 4-氰基吲哚

Database IDs

• CAS Number: 16136-52-0
• MDL Number: MFCD00152045
• PubChem SID: 160975356; 24883383
• PubChem CID: 3817602

CALCULATED PROPERTIES

• Acid pKa: 15.615056
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.928104
• LogD (pH = 7.4): 1.928104
• Log P: 1.928104
• Molar Refractivity: 42.8661 cm^3
• Polarizability: 17.431162 Å^3
• Polar Surface Area: 39.58 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 117-121 °C(lit.); 117-121°C
• Hydrophobicity(logP): 1.955

Safety Information

• Storage Warning: Harmful/Irritant/Light Sensitive/Keep Cold/Store under Argon
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-37/38-41-43
• Safety Statements: 26-36/37/39
• TSCA Listed: false
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H317-H318-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%; 98%
• Empirical Formula (Hill Notation): C9H6N2

DETAILS

Sigma Aldrich - 645532

Packaging
1, 5 g in glass bottle
Application
Reactant for preparation of tryptophan dioxygenase inhibitors as potential anticancer immunomodulators1Reactant for stereoselective preparation of γ-lactones via prolinol silyl ether catalyzed Friedel-Crafts alkylation reaction2Reactant for iridium-catalyzed borylation reactions3Reactant for parallel synthesis of N-benzylisatin oximes as JNK3 MAP kinase inhibitors4Reactant for preparation of N-aryl indoles5Reactant for preparation of conformationally restricted indole cyclopropylmethylamines as selective serotonin reuptake inhibitors6