33527-26-3

Basic information

• Product Name: 3,4-Thiophenedicarbonyl dichloride (9CI)
• Synonyms: 3,4-Thiophenedicarbonyl dichloride (9CI);Thiophene-3,4-dicarbonyl dichloride
• CAS NO: 33527-26-3
• Molecular Formula: C₆H₂Cl₂O₂S
• Molecular Weight: 209.05
• Product Categories: ACIDHALIDE
• Mol File: 33527-26-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 293.2±20.0 °C(Predicted)
• Appearance: /
• Density: 1.586±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 3,4-Thiophenedicarbonyl dichloride (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Thiophenedicarbonyl dichloride (9CI)(33527-26-3)
• EPA Substance Registry System: 3,4-Thiophenedicarbonyl dichloride (9CI)(33527-26-3)

Safety Data

• Hazardous Substances Data: 33527-26-3(Hazardous Substances Data)

Upstream product

• 4282-35-3 dimethyl thiophene-3,4-dicarboxylate 
• 20946-32-1 3,4-dimethyl 2,5-dihydrothiophene-3,4-dicarboxylate 
• 80356-26-9 (E/Z)-Dimethyl 2,3-bis-butenedioate 
• 13314-92-6 dimethyl (Z)-2,3-dimethyl-2-butenedioate 
• 766-39-2 2,3-Dimethylmaleic anhydride 
• 73926-95-1 diethyl 2-formyl-3-(diethoxymethyl)succinate 
• 53229-47-3 diethyl thiophene-3,4-dicarboxylate 
• 18853-32-2 3,4-dicyanothiophene 
• 4282-29-5 thiophene-3,4-dicarboxylic acid 

Downstream Products

• 33527-20-7 4,9-Dihydronaphtho<2,3c>thiophen-4,9-dion 
• 18354-73-9 [4-(hydroxymethyl)-3-thienyl]methanol 

Relevant articles and documents

Direct C–H Arylation as a Chemoselective Single-Step Access to π–Acceptor–π Type Building Blocks

Different from the traditional multi-step synthesis, a chemoselective direct C–H arylation is reported for the single-step synthesis of various useful π–acceptor–π (π–A–π) type building blocks for use in organic electronics. This well-optimized C–H heteroarylation exhibits good product yields, broad substrate scope, and high functional group compatibility. Applications in the efficient synthesis of a new metal-free dye sensitizer for dye-sensitized solar cells (DSSCs) are also demonstrated. (Figure presented.).

Single precursor for the synthesis of donor and acceptor units of the low band gap polymers: Synthesis of benzodithiophene and thienopyrroledione from maleic anhydride

An efficient route was developed to synthesize dimethyl thiophene-3,4-dicarboxylate from maleic anhydride. Dimethyl thiophene-3,4-dicarboxylate was used as a single precursor for synthesis of benzo[1,2-b:4,5-b′]dithiophene (BDT) and Thieno[3,4-c]pyrrole-4,6-dione (TPD) derivatives. BDT and TPD derivatives have been highly exploited as donor and acceptor units, respectively, to synthesize important donor-acceptor (D-A) conjugated polymers. BDT-based polymers were found to be one of the most efficient conjugated polymers for organic photovoltaic application. Synthesis of quinone precursor of the dihydroxybenzothiophene was accomplished by a new and unconventional methodology which includes reaction of 3,4-thiophene dicarboxylate with sodium hydride in THF. Dithienobenzoquinone dicarboxylate and dihydroxybenzodithiophene dicarboxylate were characterized structurally by single-crystal X-ray diffraction. Both compounds show strong π-stacking interaction and arrange in the parallel molecular sheets in the crystals.

Acetic anhydride mediated condensation of aromatic o-diacid dichlorides with benzimidazoles to provide electro-reducible p-dione adducts

Acetic anhydride mediates a facile and rapid condensation of benzimidazole with aromatic o-diacid dichlorides to precipitate p-dione adducts in excellent yields. Condensation with pyridine-3,4-dicarbonyl dichloride produced a 1:1 mixture of isomeric p-diones. The X-ray crystal structure of one of the latter isomers revealed unusual high density, and inter-layer separation similar to graphite. Cyclic voltammetry demonstrated that p-dione is capable of two consecutive one-electron-reductions with formal potentials influenced by the fused (hetero)aromatic and substituent effects.