5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical Properties

Melting point:

98 °C

Boiling point:

306.5±42.0 °C(Predicted)

Density 

2.139±0.06 g/cm3(Predicted)

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

Grey to Dark Blue

CAS DataBase Reference

174508-31-7

Safety Information

Hazard Codes 

Xn

Risk Statements 

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

Safety Statements 

22-26-36/37/39-24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29349990

5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine Usage And Synthesis

Chemical Properties

Needle-like solid

Uses

5,7-Dibromo-2,3-dihydrothieno[3,4-b]-1,4-dioxine is used in the preparation of 3,4-ethylenedioxythiophene oligomers with optical and redox properties.

Uses

Used as a monomer in the synthesis of poly(3,4-ethylenedioxythiophene) (PEDOT) polymer which are used in electrochromic devices.

General Description

2,5-Dibromo-3,4-ethylenedioxythiophene (DBEDOT) is a monomer which is used in the synthesis of highly conducting poly(3,4-ethylenedioxythiophene) (PEDOT) polymer. This polymer is formed by solid-state polymerisation of DBEDOT and is used widely in organic-light emitting diodes and polymer field effect transistors. DBEDOT is a well-ordered crystalline monomer and produces PEDOT polymer which has a high degree of order.

Synthesis

The general procedure for the synthesis of 2,5-dibromo-3,4-ethenyldioxythiophene from 3,4-ethenyldioxythiophene was as follows: a solution of tetrahydrofuran (THF, 20 mL) with 3,4-ethenyldioxythiophene (1.42 g, 10.60 mmol), N-bromosuccinimide (3.74 g, 12.80 mmol), and acetic acid (20 mL) was added sequentially to a round bottomed flask. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the mixture was poured into distilled water and stirred with a glass rod to promote the formation of the precipitate. Subsequently, the precipitate was collected by filtration to afford the target product 2,5-dibromo-3,4-vinyl dioxythiophene (A4) as a white solid (2.50 g, 8.30 mmol, 83% yield). The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shift δ = 4.27 (s, 4H).

References

[1] Journal of the American Chemical Society, 2000, vol. 122, # 28, p. 6746 - 6753
[2] Journal of Organic Chemistry, 2003, vol. 68, # 13, p. 5357 - 5360
[3] Organic Letters, 2018, vol. 20, # 16, p. 4728 - 4731
[4] Journal of the American Chemical Society, 2000, vol. 122, # 41, p. 10121 - 10125
[5] Macromolecules, 2004, vol. 37, # 11, p. 4087 - 4098

5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine(174508-31-7)Related Product Information

• Tetrabutylammonium perchlorate
• Triethoxyvinylsilane
• N-Vinyl-2-pyrrolidone
• 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE
• 3,4-Ethylenedioxythiophene
• Isobutyl vinyl ether
• VINYL PROPIONATE
• Silicone rubber,methyl-vinyl
• Vinyl ester resin
• Vinyl resin
• 2,5-Dibromothiophene
• 3,4-Dimethoxythiophene
• 5-BROMO-2,3-DIHYDROTHIENO[3,4-B][1,4]DIOXINE
• 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine