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1,8-Diazafluoren-9-one

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1,8-Diazafluoren-9-one (DFO) is an aromatic ketone first synthesized in 1950. It is used to find fingerprints on porous surfaces.[1][2] It makes fingerprints glow when they are lit by blue-green light.[2]

1,8-Diazafluoren-9-one
1,8-Diazafluoren-9-one
Names
Preferred IUPAC name
9H-Cyclopenta[1,2-b:4,3-b′]dipyridin-9-one
Other names
DFO
9H-1,8-Diazafluoren-9-one
9H-Pyrido[3′,2′:3,4]cyclopenta[1,2-b]pyridin-9-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C11H6N2O/c14-11-9-7(3-1-5-12-9)8-4-2-6-13-10(8)11/h1-6H checkY
    Key: FOSUVSBKUIWVKI-UHFFFAOYSA-N checkY
  • InChI=1/C11H6N2O/c14-11-9-7(3-1-5-12-9)8-4-2-6-13-10(8)11/h1-6H
    Key: FOSUVSBKUIWVKI-UHFFFAOYAH
  • O=C1C3=C(C=CC=N3)C2=C1N=CC=C2
  • O=C3c1ncccc1c2c3nccc2
Properties
C11H6N2O
Molar mass 182.182 g·mol−1
Appearance Yellow powder
Melting point 229–233 °C (444–451 °F; 502–506 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

DFO reacts with amino acids present in the fingerprint to form highly fluorescent derivatives. Excitation with light at ~470 nm results in emission at ~570 nm.[2]

References

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  1. ^ Lewkowicz, Aneta; Baranowska, Karolina; Bojarski, Piotr; Józefowicz, Marek (2019). "Solvent dependent spectroscopic properties of fingerprint reagent - 1,8-Diazafluoren-9-one". Journal of Molecular Liquids. 285: 754–765. doi:10.1016/j.molliq.2019.04.110. S2CID 149852434.
  2. ^ a b c Pounds, C. Anthony; Grigg, Ronald; Mongkolaussavaratana, Theeravat (1 January 1990). "The Use of 1,8-Diazafluoren-9-one (DFO) for the Fluorescent Detection of Latent Fingerprints on Paper. A Preliminary Evaluation". Journal of Forensic Sciences. 35 (1): 169–175. doi:10.1520/JFS12813J.
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