6-Bromothiochroman-4-one Chemical Properties

Melting point:

66-69℃

Boiling point:

356.7±42.0 °C(Predicted)

Density 

1.638±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Appearance

Off-white to light yellow Solid

Safety Information

Risk Statements 

43

Safety Statements 

36/37

HS Code 

29349990

6-Bromothiochroman-4-one Usage And Synthesis

Chemical Properties

Orange solid

Synthesis

General procedure for the synthesis of 6-bromothiochroman-4-one and 6,8-dibromothiochroman-4-one from thiochroman-4-one: Anhydrous aluminum trichloride (1.81 g, 13.5 mmol) and methylene chloride (1 mL) were added to a round bottom flask at room temperature. After stirring for about 7 min under nitrogen protection, a solution of thiocolchroman-4-one (1.11 g, 6.77 mmol) in dichloromethane (1 mL) was slowly added. Stirring was continued for 10 minutes and then a solution of bromine (1.19 g, 7.44 mmol) in dichloromethane (2 mL) was added dropwise. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was poured into ice water (50 mL) and the aqueous phase was extracted with ethyl acetate three times. The organic phases were combined, washed once with saturated saline and dried over anhydrous sodium sulfate. The crude product was purified by fast column chromatography (15% ethyl acetate/85% hexane) to give a mixture of 6-bromothiochroman-4-one (0.648 g, 34% purity, 13% yield) and 6,8-dibromothiochroman-4-one (66% purity, 20% yield).The NMR data for 6,8-dibromothiochroman-4-one were as follows:1H NMR (300 MHz , CDCl3, δ): 8.18 (dd, J = 2.2, 0.7 Hz, Ar-H, 1H), 7.77 (dd, J = 2.2, 0.7 Hz, Ar-H, 1H), 3.22 (m, CH2, 2H), 2.94 (m, CH2, 2H). 13C NMR (75 MHz, CDCl3): δ 192.0, 142.5 , 139.1, 136.0, 131.0, 122.2, 118.2, 37.8, 26.0.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 16, p. 4405 - 4409
[2] Patent: US2009/76076, 2009, A1. Location in patent: Page/Page column 24

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