1-[6-(dimethylamino)naphthalen-2-yl]propan-1-one

• ChemBase ID: 155889
• Molecular Formular: C15H17NO
• Molecular Mass: 227.30158
• Monoisotopic Mass: 227.13101417
• SMILES: CCC(=O)c1ccc2cc(ccc2c1)N(C)C
• Canonical SMILES: CCC(=O)c1ccc2c(c1)ccc(c2)N(C)C
• InChI: InChI=1S/C15H17NO/c1-4-15(17)13-6-5-12-10-14(16(2)3)8-7-11(12)9-13/h5-10H,4H2,1-3H3
• InChIKey: MPPQGYCZBNURDG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[6-(dimethylamino)naphthalen-2-yl]propan-1-one
• IUPAC Traditional name: prodan
• Synonyms: 2-(Dimethylamino)-6-propionylnaphthalene; 6-Propionyl-2-(dimethylamino)naphthalene; Prodan; N,N-Dimethyl-6-propionyl-2-naphthylamine; 1-[6-(Dimethylamino)-2-naphthalenyl]-1-propanone; 2-Propionyl-6-dimethyl-aminonaphthalene; 6-Propionyl-2-(N,N-dimethylamino)naphthalene; 6-Propanoyl-2-(N,N-dimethylamino)naphthalene; Prodan (fluorophore); Prodan

Database IDs

• CAS Number: 70504-01-7
• MDL Number: MFCD00056615
• Beilstein Number: 2723587
• PubChem SID: 24865986; 162250027
• PubChem CID: 107729

CALCULATED PROPERTIES

• Acid pKa: 16.61678
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.2195904
• LogD (pH = 7.4): 3.3273866
• Log P: 3.3289497
• Molar Refractivity: 71.9665 cm^3
• Polarizability: 28.31168 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetone: soluble; acetonitrile: soluble; DMF: soluble; methanol: soluble
• Melting Point: 137 °C(lit.)
• Fluorescence: λex 361 nm; λem 498 nm in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C15H17NO

DETAILS

Sigma Aldrich - 41525

Other Notes
Fluorescence of spectrin-bound Prodan1

Toronto Research Chemicals - P755865

Prodan is widely used as a fluorescent molecule probe because of its significant Stokes shift in polar solvents.

REFERENCES

• Weber, G., et al.: Biochemistry, 1979, 18, 3075 (1979)
• Chong, P., et al.: Biochemistry, 27, 399 (1979)
• Jurkiewicz, P., et al.: J. Fluoresc., 15, 883 (1979)