ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Thiophene compounds 2,5-DIBROMO-3,4-DINITROTHIOPHENE

2,5-DIBROMO-3,4-DINITROTHIOPHENE

Product Name2,5-DIBROMO-3,4-DINITROTHIOPHENE
CAS52431-30-8
MFC4Br2N2O4S
MW331.93
EINECS676-535-4
MOL File52431-30-8.mol

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
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ALFA	English

Usage And Synthesis

Chemical Properties

Light Orange Solid

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.

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.

Synthesis

3141-27-3

52431-30-8

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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