1H-indole-3-carbonitrile

• ChemBase ID: 59017
• Molecular Formular: C9H6N2
• Molecular Mass: 142.15734
• Monoisotopic Mass: 142.0530982
• SMILES: c1ccc2[nH]cc(c2c1)C#N
• Canonical SMILES: N#Cc1c[nH]c2c1cccc2
• InChI: InChI=1S/C9H6N2/c10-5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H
• InChIKey: CHIFTAQVXHNVRW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indole-3-carbonitrile
• IUPAC Traditional name: 3-cyanoindole
• Synonyms: 1H-Indole-3-carbonitrile; 1H-Indole-3-carbonitrile; 3-Cyanoindole; NSC 24935; 3-Indolecarbonitrile; 3-Cyanoindole; 3-Cyanoindole; Indole-3-carbonitrile; 3-吲哚甲腈; 3-氰基吲哚; 吲哚-3-甲腈

Database IDs

• CAS Number: 5457-28-3
• EC Number: 000-000-0
• MDL Number: MFCD00022717
• Beilstein Number: 120888
• PubChem SID: 162063780; 24861537
• PubChem CID: 230282

CALCULATED PROPERTIES

• Acid pKa: 13.962229
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.928104
• LogD (pH = 7.4): 1.9281039
• Log P: 1.928104
• Molar Refractivity: 42.8661 cm^3
• Polarizability: 17.433369 Å^3
• Polar Surface Area: 39.58 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 177-182°C; 179-182 °C(lit.); 179-182°C; 181 - 182°C
• Hydrophobicity(logP): 2.085

Safety Information

• Storage Warning: IRRITANT; Light Sensitive
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38; 22-36/37/38
• Safety Statements: 26-36/37; 26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 95+%; 97%; 98%
• Empirical Formula (Hill Notation): C9H6N2

DETAILS

Sigma Aldrich - 347949

Packaging
1, 5 g in glass bottle
Application
Reactant for preparation of:
• Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1
• Inhibitors of the C-terminal domain of RNA polymerase II with antitumor activities
• 4-substituted β-lactams2
• Biologically active Indoles3
• Inhibitors of glycogen synthase kinase 3β (GSK-3)4
• HIV-1 integrase inhibitors5
• Indole fragments as inosine monophosphate dehydrogenase (IMPDH) inhibitors6
• Aziridinomitosene skeleton7
• Potential antiviral agents8Reactant for:
• Intramolecular oxidative C-H coupling reactions with applications in medium-ring synthesis techniques9