2,5-Dibromo-3,4-dinitrothiophene

Name: 2,5-Dibromo-3,4-dinitrothiophene
Brand: ChemScene
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CAS No. 52431-30-8
Cat. No. CS-W013934
Purity≥98%
MDL No.MFCD00015537

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2,5-Dibromo-3,4-dinitrothiophene|CS-W013934

Structure of 52431-30-8

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General Information

CAS No. 52431-30-8
Cat. No. CS-W013934
Purity ≥98%
MDL No. MFCD00015537
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄Br₂N₂O₄S
Molecular Weight 331.93
Synonym(s) NSC 84661; 2,5-Dibromo-3,4-dinitrothiophene
SMILES O=[N+](C1=C(Br)SC(Br)=C1[N+]([O-])=O)[O-]

Description

2,5-Dibromo-3,4-dinitrothiophene features a highly electron-deficient thiophene core stabilized by dual bromine and nitro substituents. This configuration enables robust coupling in transition-metal-catalyzed reactions, particularly in cross-coupling protocols requiring high reactivity. The molecule exhibits enhanced stability under standard handling conditions while maintaining strong electrophilic character at the ring positions.

Application

2,5-Dibromo-3,4-dinitrothiophene serves as a versatile building block for heterocyclic synthesis, enabling direct functionalization at the 2- and 5-positions via palladium-catalyzed cross-coupling reactions. The dinitro groups enhance electrophilicity at C-3 and C-4, facilitating nucleophilic substitution under mild conditions. Its bench-stable crystalline form supports straightforward handling and purification, making it well-suited for iterative synthesis of complex thiophene-based scaffolds in medicinal chemistry and materials science applications.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 86.28
LogP 3.0895
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Nitro compounds

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Thiophene compounds

Key Words

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2,5-Dibromo-3,4-dinitrothiophene

CAS No. 52431-30-8

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