2,8-Dibromodibenzothiophene Chemical Properties

Melting point:

226°C

Boiling point:

436.5±25.0 °C(Predicted)

Density 

1.905

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

almost transparency in hot Toluene

form 

powder to crystal

color 

White to Almost white

InChI

InChI=1S/C12H6Br2S/c13-7-1-3-11-9(5-7)10-6-8(14)2-4-12(10)15-11/h1-6H

InChIKey

WNEXSUAHKVAPFK-UHFFFAOYSA-N

SMILES

C12=CC=C(Br)C=C1C1=CC(Br)=CC=C1S2

CAS DataBase Reference

31574-87-5(CAS DataBase Reference)

Safety Information

Risk Statements 

20

Safety Statements 

22-26-36-24/25

RIDADR 

UN2811

HazardClass 

6.1

HS Code 

29420000

2,8-Dibromodibenzothiophene Usage And Synthesis

Uses

2,8-Dibromodibenzothiophene is used as a starting material or intermediate for synthesizing novel 2,8-disubstituted dibenzothiophenes via palladium-catalyzed C-N or C-C bond formation. 2,8-Dibromodibenzothiophene is also used as a starting material to create organic electroluminescent derivatives.

Chemical Properties

White to light yellow solid

Uses

2,8-Dibromodibenzothiophene is used as a starting material or intermediate for synthesizing novel 2,8-disubstituted dibenzothiophenes via palladium-catalyzed C-N or C-C bond formation. 2,8-Dibromodibenzothiophene is also used as a starting material to create organic electroluminescent derivatives.

Synthesis

The general procedure for the synthesis of 2,8-dibromodibenzothiophene from dibenzothiophene was as follows: dibenzothiophene (15.1552 g, 82.25 mmol) was dissolved in chloroform (150 mL) and bromine (13.0 mL, 253.72 mmol) was slowly added dropwise at 0 °C in an ice bath. After the dropwise addition, the reaction mixture was kept at 0 °C for 2 hours. Subsequently, the reaction system was slowly warmed to room temperature and stirring was continued for 3 days. After completion of the reaction, excess methanol was added to the mixture and stirred for 30 min to precipitate the product. The white solid product was collected by vacuum filtration and washed with excess methanol to finally obtain 2,8-dibromodibenzothiophene (22.87 g, 66.86 mmol, 81% yield).

References

[1] Chemistry - An Asian Journal, 2017, vol. 12, # 5, p. 552 - 560
[2] Patent: WO2017/13420, 2017, A1. Location in patent: Page/Page column 11
[3] Journal of Materials Chemistry, 2003, vol. 13, # 6, p. 1351 - 1355
[4] Journal of the American Chemical Society, 2010, vol. 132, # 12, p. 4466 - 4476
[5] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2096 - 2105

2,8-Dibromodibenzothiophene(31574-87-5)Related Product Information

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• 4,6-DIMETHYLDIBENZOTHIOPHENE
• 3,4-Dibromothiophene
• DBDCB
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• 1,2-Dibromopropane
• 2,5-Dibromothiophene
• 5-Bromobenzo[c]thiophene
• 2-BROMODIBENZOTHIOPHENE
• Bromine
• Thiophene
• 2,8-Dibromodibenzothiophene 5,5-dioxide