5-BROMO-2 2'-BITHIOPHENE 96 Chemical Properties

Melting point:

29-32 °C(lit.)

Boiling point:

50 °C(Press: 0.006 Torr)

Density 

1.635±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

Appearance

Light yellow to green yellow Solid

InChIKey

OMOAIGVIYUXYAU-UHFFFAOYSA-N

Safety Information

WGK Germany 

3

5-BROMO-2 2'-BITHIOPHENE 96 Usage And Synthesis

Uses

5-Bromo-2,2′-bithiophene may be used in the synthesis of trimethyl-[2,2′;5′,2″;5″,2″]quaterthiophen-5-yl-silane (4TTMS) and 5-hexylsulfanyl-2,2′:5′,2′′-terthiophene.

General Description

5-Bromo-2,2′-bithiophene is a bromothiophene derivative. Its reaction with various aryl iodides bearing an electron-donating or electron-withdrawing substituent has been described. It can be synthesized from 2,2′-bithiophene.

Synthesis

General procedure for the synthesis of 5-bromo-2,2-bithiophene from bithiophene: 3 g (18 mmol) of 2,2'-bithiophene and 50 mL of N,N-dimethylformamide (DMF) were placed in a 250 mL two-necked round-bottomed flask and dissolved by stirring. A solution of 3.2 g (18 mmol) of N-bromosuccinimide (NBS) dissolved in 10 mL of DMF was added slowly and dropwise under cooling in an ice bath. After completion of the reaction, the reaction mixture was extracted with dichloromethane (DCM) and the organic phase was collected. Purification by recrystallization from methanol (MeOH) gave 2.5 g of light yellow solid product in 56% yield. The resulting intermediate (1) was characterized by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3, 400 MHz) with the following chemical shifts: δ= 6.91 (1H, d), 6.96 (1H, d), 7.00 (1H, dd), 7.22 (1H).

References

[1] Patent: US6342610, 2002, B2. Location in patent: Page column 58
[2] ACS Catalysis, 2016, vol. 6, # 2, p. 1113 - 1121
[3] RSC Advances, 2017, vol. 7, # 89, p. 56586 - 56593
[4] Chemistry of Materials, 2010, vol. 22, # 7, p. 2325 - 2332
[5] Journal of Organic Chemistry, 1996, vol. 61, # 20, p. 6906 - 6921

5-BROMO-2 2'-BITHIOPHENE 96(3480-11-3)Related Product Information

• ALPHA-SEXITHIOPHENE
• α,ω-Dihexylquaterthiophene, 5,5μ-Bis(3-hexyl-2-thienyl)-2,2μ-bithiophene, DH-4T
• O-QUARTERPHENYL
• 5,5''-dibromo-[2,2':5',2"]terthiohene
• 5,5'-Dibromo-2,2'-bithiophene
• 5-BROMO-2 2'-BITHIOPHENE 96
• 5-BROMO-2,2'-BITHIOPHENE-5'-CARBOXALDEHYDE
• 5''-BROMO-2,2':5',2''-TERTHIOPHENE-5-CARBOXALDEHYDE
• 5''-BROMO-3'-DECYL-2,2',5',2''-TERTHIOPHENE
• 5-BROMO-3'-DECYL-2,2':5',2''-TERTHIOPHENE
• 2-Bromoterthiophene
• RARECHEM AL BF 0485
• RARECHEM AL BE 0509
• RARECHEM AL BI 0485
• RARECHEM AL BI 0509
• RARECHEM AL BD 0509
• RARECHEM AL BK 0485
• SALOR-INT L164909-1EA