QUINOXALINE-6-CARBALDEHYDE Chemical Properties

Melting point:

130-131 °C

Boiling point:

319.8±22.0 °C(Predicted)

Density 

1.299±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-0.24±0.30(Predicted)

form 

solid

color 

Pale brown

InChI

InChI=1S/C9H6N2O/c12-6-7-1-2-8-9(5-7)11-4-3-10-8/h1-6H

InChIKey

UGOIXUFOAODGNI-UHFFFAOYSA-N

SMILES

N1C2C(=CC(C=O)=CC=2)N=CC=1

CAS DataBase Reference

130345-50-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

26-39

HazardClass 

IRRITANT

HS Code 

2933998090

QUINOXALINE-6-CARBALDEHYDE Usage And Synthesis

Uses

Quinoxaline-6-carbaldehyde can be used as raw material or intermediate of organic synthesis. It is used in the synthesis of 6-(bromomethyl)quinoxaline and ligands for targeting RNA.

Synthesis

The general procedure for the synthesis of quinoxaline-6-carbaldehyde from quinoxaline-6-carbonyl chloride is as follows: in an 11-liter three-neck flask under argon protection, quinoxaline-6-carbonyl chloride was dissolved in 600 mL of 1,2-dimethoxyethane (DME). An equimolar amount of lithium tri-tert-butoxyaluminum hydride (LiAlH(Ot-Bu)3) was slowly added to this solution over a period of 1.5 hours at -78 °C. The reaction was stirred continuously at -78 °C for 5 hours. Upon completion of the reaction, the reaction was quenched by careful addition of ice water, followed by dilution of the reaction mixture with ethyl acetate (AcOEt) and filtration through a diatomaceous earth pad. The organic and aqueous layers were separated and the organic phase was washed with saturated sodium bicarbonate (NaHCO3) solution. After evaporation of the solvent under reduced pressure, quinoxaline-6-carbaldehyde was obtained in 73% yield and the product was a pale yellow solid. High performance liquid chromatography (HPLC) analysis showed a retention time of 1.49 min. Liquid chromatography-mass spectrometry (LC-MS) analysis showed a retention time of 0.81 min at m/z of 159.37 [M+H]+ in ESI positive ion mode. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3) data were as follows: δ 10.28 (s, 1H), 8.97 (s, 2H), 8.61 (s, 1H), 8.27 (q, J=6 Hz, 9 Hz, 2H).

References

[1] Patent: WO2004/7491, 2004, A1. Location in patent: Page 69

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