2-BROMOBENZO[B]THIOPHENE Chemical Properties

Melting point:

44.5-45℃

Boiling point:

284.7±13.0 °C(Predicted)

Density 

1.649±0.06 g/cm3(Predicted)

Flash point:

>110℃

storage temp. 

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

form 

solid

color 

White

InChI

InChI=1S/C8H5BrS/c9-8-5-6-3-1-2-4-7(6)10-8/h1-5H

InChIKey

WIFMYMXKTAVDSQ-UHFFFAOYSA-N

SMILES

C1(Br)SC2=CC=CC=C2C=1

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-36-22

Safety Statements 

22-26-36/37/39

WGK Germany 

3

Hazard Note 

Harmful

HS Code 

29349990

2-BROMOBENZO[B]THIOPHENE Usage And Synthesis

Chemical Properties

White solid

Uses

2-Bromobenzo[b]thiophene is used in the stereoselective preparation of halogenated benzoxazines via enantioselective halocyclization of o-anilidostyrenes using chiral anion phase-transfer catalysts.

Synthesis

To a solution of benzo[b]thiophene (2.0 g, 15 mmol) in tetrahydrofuran (20 mL) was slowly added n-butyllithium (2.5 M hexane solution, 12 mL, 30 mmol) dropwise at -70 °C and under nitrogen protection. The reaction mixture was stirred continuously at this temperature for 30 minutes. Subsequently, N-bromosuccinimide (5.3 g, 30 mmol) was added and the reaction system was slowly warmed from -70 °C to room temperature over 1 hour. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (20 mL) followed by extraction with ethyl acetate (3 x 30 mL). The organic phases were combined, concentrated in vacuum, and the residue was purified by silica gel column chromatography [eluent: petroleum ether/ethyl acetate = 100:1] to afford 2-bromobenzothiophene (0.50 g, 16% yield) as a white solid.

References

[1] Patent: WO2006/56418, 2006, A2. Location in patent: Page/Page column 68-69
[2] Chemistry - An Asian Journal, 2014, vol. 9, # 9, p. 2542 - 2547,6
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 3034 - 3038
[4] Patent: WO2017/69980, 2017, A1. Location in patent: Paragraph 00274; 00275
[5] Journal of the American Chemical Society, 1952, vol. 74, p. 664

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