Thieno[2,3-b]pyridine (8CI,9CI) Chemical Properties

Boiling point:

236.5±13.0 °C(Predicted)

Density 

1.272±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

pka

4.54±0.30(Predicted)

Appearance

Colorless to light yellow Liquid

Safety Information

HS Code 

2934999090

Thieno[2,3-b]pyridine (8CI,9CI) Usage And Synthesis

Synthesis

Thieno[2,3-b]pyridine was synthesized as follows: 1.08 g (8.3 mmol) of 2-nitrothiophene and 16 mL of concentrated hydrochloric acid were sequentially added to a vigorously stirred mixture at 30 °C. Subsequently, a total of 2.08 g of granulated tin was added in batches of 0.42 g. After most of the tin was dissolved, 6 mL of ethanol and 0.5 g of anhydrous zinc chloride were added to the mixture and the mixture was heated to 85°C. The mixture was then stirred vigorously at 30°C for 1 hour. Next, 1.4 g (6.5 mmol) of malonaldehyde tetraethyl acetal (purchased from Aldrich Chemical Co.) dissolved in 3 mL of ethanol was added all at once. The reaction mixture was maintained at 85 °C for 1 h before the reaction was quenched by pouring 9 g of ice. The aqueous mixture was alkalized with concentrated ammonia solution and subsequently extracted with three 5 mL dichloromethane. The organic phases were combined and distilled to give 0.4 g (44% yield) of the target product thieno[2,3-b]pyridine as a light yellow liquid.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 20, p. 1952 - 1956
[2] Patent: WO2011/79804, 2011, A1. Location in patent: Page/Page column 33
[3] Patent: US2012/245178, 2012, A1. Location in patent: Page/Page column 19

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