2,5-DIBROMO-3,4-DINITROTHIOPHENE Chemical Properties

Melting point:

137°C

Boiling point:

341.2±37.0 °C(Predicted)

Density 

2.459±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetone, Methanol

form 

Solid

color 

Light Orange

Water Solubility 

Insoluble in water.

BRN 

218219

InChI

InChI=1S/C4Br2N2O4S/c5-3-1(7(9)10)2(8(11)12)4(6)13-3

InChIKey

AHGHPBPARMANQD-UHFFFAOYSA-N

SMILES

C1(Br)SC(Br)=C([N+]([O-])=O)C=1[N+]([O-])=O

CAS DataBase Reference

52431-30-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:ALFA

2,5-DIBROMO-3,4-DINITROTHIOPHENE Usage And Synthesis

Chemical Properties

Light Orange Solid

Uses

Reatant in the synthesis of bromodinitro compound, polymers via stille coupling. 3,4-diaminothiophene was obtained from the reduction of 2,5-dibromo-3,4-dinitrothiophene.

Uses

This monomer is useful in the Pd catalyzed Stille coupling to make conjugated thiophene oligomers or co-oligomers. The corresponding amine(s) can be obtained by subsequent reduction.

Synthesis

GENERAL STEPS: Preparation The synthesis of 2,5-dibromo-3,4-dinitrothiophene from 2,5-dibromothiophene in Example 1 was carried out as follows: firstly, a mixed acid was prepared by mixing 11 mL of fuming nitric acid with 20 mL of fuming sulfuric acid. Subsequently, 13 mL of concentrated sulfuric acid was added to this mixed acid to prepare a reaction solution. To this solution, 7.5 g (31 mmol) of 2,5-dibromothiophene was slowly added dropwise while maintaining the reaction temperature between 20 and 30 °C by means of a water bath with continuous stirring for 3 hours. Upon completion of the reaction, the reaction solution was transferred to a vessel containing 90 g of ice to terminate the reaction. The resulting solid product was collected by filtration and purified by recrystallization with methanol to give the final target product 2,5-dibromo-3,4-dinitrothiophene. The yield based on 2,5-dibromothiophene was 66%.

References

[1] Journal of Chemical Crystallography, 2007, vol. 37, # 6, p. 387 - 398
[2] Dyes and Pigments, 2012, vol. 92, # 1, p. 674 - 680
[3] Patent: KR2018/17709, 2018, A. Location in patent: Paragraph 0173; 0176; 0180-0182
[4] European Journal of Organic Chemistry, 2012, # 28, p. 5540 - 5551
[5] Macromolecules, 2010, vol. 43, # 2, p. 697 - 708

2,5-DIBROMO-3,4-DINITROTHIOPHENE(52431-30-8)Related Product Information

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