ChemicalBook Product Catalog Chemical Reagents Organic reagents The polycyclic compound 4,5-DIAZAFLUOREN-9-ONE

4,5-DIAZAFLUOREN-9-ONE

Product Name4,5-DIAZAFLUOREN-9-ONE
CAS50890-67-0
MFC11H6N2O
MW182.18
EINECS
MOL File50890-67-0.mol

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.)
InChI	1S/C11H6N2O/c14-11-7-3-1-5-12-9(7)10-8(11)4-2-6-13-10/h1-6H
InChIKey	PFMTUGNLBQSHQC-UHFFFAOYSA-N
SMILES	O=C1c2cccnc2-c3ncccc13
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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English

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

66-71-7

50890-67-0

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

4,5-DIAZAFLUOREN-9-ONE

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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