2,6-DICHLOROQUINOLINE Chemical Properties

Melting point:

161-164 °C (lit.)

Boiling point:

172°C/13mmHg(lit.)

Density 

1.407±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-0.48±0.43(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29334900

MSDS

• Language:English Provider:SigmaAldrich

2,6-DICHLOROQUINOLINE Usage And Synthesis

Chemical Properties

White to orange to tan crystal or powder

Uses

2,6-Dichloroquinoline may be used in the preparation of poly(quinoline-2,6-diyl), via electrochemical polymerization.

Synthesis Reference(s)

The Journal of Organic Chemistry, 67, p. 7884, 2002 DOI: 10.1021/jo016196i

General Description

2,6-Dichloroquinoline can be synthesized from 6-chloroquinoline. It can also be prepared from the corresponding 2-vinylaniline.

Synthesis

Synthesis of 2,6-dichloroquinoline: 180 mg of 6-chloroquinolin-2(1H)-one was dissolved in 3 mL of phosphorus oxychloride (POCl3) and the reaction mixture was heated to reflux for 3 h. The reaction was carried out on a rotary evaporator. Upon completion of the reaction, the excess POCl3 was removed by rotary evaporator.After the reaction mixture was cooled to room temperature, the residue was treated with ice water and the precipitated solid was collected by filtration and dried to give the product in the form of a green powder in 90% yield. The synthesis of the compound followed the general method described in claim 5. The theoretical mass-to-charge ratio (m/z) of the compound C9H5Cl2N was 198; the measured value was 198. LC-MS analysis showed that the m/z of the molecular ion peak [M+2]+ was 200.1. 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.04 (1H, d, J = 7.8 Hz), 7.97 (1H, d, J = 8.8 Hz), 7.81 (1H, d, J = 1.9 Hz), 7.68 (1H, dd, J = 9.8 Hz, J = 2.9 Hz), 7.42 (1H, d, J = 8.8 Hz).

References

[1] Patent: US2011/190343, 2011, A1. Location in patent: Page/Page column 27
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7220 - 7231
[3] Journal of Medicinal Chemistry, 2002, vol. 45, # 14, p. 3130 - 3137
[4] Ann. Inst. Pasteur, 1930, vol. 44, p. 719,737

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