2-azatricyclo[6.3.1.04,12]dodeca-1(11),4(12),5,7,9-pentaen-3-one

• ChemBase ID: 83321
• Molecular Formular: C11H7NO
• Molecular Mass: 169.17938
• Monoisotopic Mass: 169.05276385
• SMILES: [nH]1c(=O)c2cccc3c2c1ccc3
• Canonical SMILES: O=c1[nH]c2c3c1cccc3ccc2
• InChI: InChI=1S/C11H7NO/c13-11-8-5-1-3-7-4-2-6-9(12-11)10(7)8/h1-6H,(H,12,13)
• InChIKey: GPYLCFQEKPUWLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-azatricyclo[6.3.1.0^4,^1^2]dodeca-1(11),4(12),5,7,9-pentaen-3-one; 2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),4(12),5,7,9-pentaen-3-one; 2-azatricyclo[6.3.1.0^4,^1^2]dodeca-1(12),4,6,8,10-pentaen-3-one
• IUPAC Traditional name: 2-azatricyclo[6.3.1.0^4,^1^2]dodeca-1(11),4(12),5,7,9-pentaen-3-one; 2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(11),4(12),5,7,9-pentaen-3-one; benz(cd)indol-2(1H)-one
• Synonyms: NSC 25094; Benz[cd]indol-2(1H)-one; 1,8-Naphthostyril; Benz[cd]indol-2(1H)-one; 1,2-Dihydrobenzo[cd]indol-2-one, tech; 2-azatricyclo[6.3.1.0^{4,12}]dodeca-1(12),4,6,8,10-pentaen-3-one; 萘二甲酰亚胺

Database IDs

• CAS Number: 130-00-7
• EC Number: 204-973-4
• MDL Number: MFCD00009748
• PubChem SID: 162070440; 24860382
• PubChem CID: 67222

CALCULATED PROPERTIES

• Acid pKa: 10.56809
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.081358
• LogD (pH = 7.4): 2.0810814
• Log P: 2.0813615
• Molar Refractivity: 51.9837 cm^3
• Polarizability: 20.167452 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 173 - 178°C; 173-178 °C(lit.); 173-178°C
• Hydrophobicity(logP): 1.802

Safety Information

• Storage Warning: Harmful/Irritant
• RTECS: DE3202000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%
• Grade: technical grade
• Empirical Formula (Hill Notation): C11H7NO

DETAILS

Sigma Aldrich - 336467

Packaging
1, 5 g in glass bottle
Application

• Reactant in photo-Fries rearrangement1
• Reactant in preparation of potential antitumor agents2
• Reactant in synthesis of inhibitors of thymidylate synthase3