4,5-DIAZAFLUOREN-9-ONE Chemical Properties

Melting point:

214-217 °C (lit.)

Boiling point:

396.3±17.0 °C(Predicted)

Density 

1.387±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Soluble in dichloromethane, tetrahydrofuran, chloroform, benzene, toluene and polar organic solvents. Insoluble in diethyl ether and alkanes.

form 

powder to crystal

pka

1.22±0.20(Predicted)

color 

Light yellow to Yellow to Orange

λmax

340nm(H2O)(lit.)

InChIKey

PFMTUGNLBQSHQC-UHFFFAOYSA-N

CAS DataBase Reference

50890-67-0

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

4,5-DIAZAFLUOREN-9-ONE Usage And Synthesis

Chemical Properties

Yellow crystal

Uses

4,5-Diazafluoren-9-one behaves like cyclopentadienones and reacts with [Cp*Co(C2H4)2] to form air -stable sandwich-type complexes [Cp*Co(η4-2)].

Synthesis

The general procedure for the synthesis of 4,5-diazafluoren-9-one from 1,10-phenanthroline was as follows: 1,10-phenanthroline (4.0 g, 22.2 mmol) and potassium hydroxide (KOH, 4.0 g, 71.3 mmol) were dissolved in water (250 mL), heated to boiling and maintained for 1 hour. Subsequently, a hot solution of potassium permanganate (KMnO4, 10.0 g, 63.3 mmol) dissolved in water (150 mL) was added slowly and dropwise over about 1 hour. The reaction mixture was continued to be boiled for 2 hours and then thermally filtered. After cooling the orange colored filtrate, it was extracted with chloroform. The organic extracts were combined and dried with anhydrous sodium sulfate (Na2SO4). After removal of solvent, the crude product was obtained. Further purification was carried out by silica gel column chromatography using acetone/petroleum ether (2:1, v/v) as eluent, resulting in pure 4,5-diazafluoren-9-one as a yellow solid (2 g, 50% yield).1H NMR (CDCl3) data were as follows: δ= 8.80 (d, 2H), 7.96 (d, 2H), 7.35 (d, 2H).

References

[1] Organic Letters, 2005, vol. 7, # 10, p. 1979 - 1982
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 2000, # 6, p. 971 - 980
[3] Doklady Chemistry, 2012, vol. 442, # 2, p. 50 - 56
[4] Polyhedron, 2015, vol. 87, p. 135 - 140
[5] Chemistry of Materials, 2012, vol. 24, # 4, p. 643 - 650

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