2-{1-azatricyclo[7.3.1.05,13]trideca-5,7,9(13)-trien-7-ylmethylidene}propanedinitrile

• ChemBase ID: 155961
• Molecular Formular: C16H15N3
• Molecular Mass: 249.3104
• Monoisotopic Mass: 249.1265975
• SMILES: c1c(cc2c3c1CCCN3CCC2)C=C(C#N)C#N
• Canonical SMILES: N#CC(=Cc1cc2CCCN3c2c(c1)CCC3)C#N
• InChI: InChI=1S/C16H15N3/c17-10-13(11-18)7-12-8-14-3-1-5-19-6-2-4-15(9-12)16(14)19/h7-9H,1-6H2
• InChIKey: LROAUBRDKLVBCP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{1-azatricyclo[7.3.1.0^5,^1^3]trideca-5,7,9(13)-trien-7-ylmethylidene}propanedinitrile
• IUPAC Traditional name: 2-{1-azatricyclo[7.3.1.0^5,^1^3]trideca-5,7,9(13)-trien-7-ylmethylidene}propanedinitrile
• Synonyms: 9-Julolidinylmethylenemalononitrile; DCVJ; 9-(2,2-Dicyanovinyl)julolidine

Database IDs

• CAS Number: 58293-56-4
• MDL Number: MFCD01747392
• Beilstein Number: 413882
• PubChem SID: 162250099; 24886389
• PubChem CID: 2963

CALCULATED PROPERTIES

• Polarizability: 27.780691 Å^3
• Polar Surface Area: 50.82 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.203625
• LogD (pH = 7.4): 3.2489095
• Log P: 3.2495186
• Molar Refractivity: 77.3426 cm^3

PROPERTIES

Physical Property

• Solubility: chloroform: soluble; DMSO: soluble
• Fluorescence: λex 433 nm; λem 500 nm in 50 mM Tris pH 8.0; 40% glycerol

Safety Information

• RTECS: OO4445000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C16H15N3

DETAILS

Sigma Aldrich - 72335

Other Notes
Fluorescent probe for binding to proteins etc., quantum yield increases by decreasing free rotation; abs at ~450 nm, em at 480-505 nm (solvent dep.)1,2