Thiophene-3,4-dicarbonyl dichloride

Base Information

• Chemical Name: Thiophene-3,4-dicarbonyl dichloride
• CAS No.: 33527-26-3
• Molecular Formula: C6H2 Cl2 O2 S
• Molecular Weight: 209.05
• DSSTox Substance ID: DTXSID10565655
• Wikidata: Q82450869
• Mol file: 33527-26-3.mol

Synonyms:33527-26-3;Thiophene-3,4-dicarbonyl dichloride;thiophene-3,4-dicarbonyl chloride;3,4-Thiophenedicarbonyl dichloride (9CI);DTXSID10565655

Chemical Property of Thiophene-3,4-dicarbonyl dichloride

Chemical Property:

• Boiling Point: 293.2±20.0 °C(Predicted)
• PSA: 62.38000
• Density: 1.586±0.06 g/cm3(Predicted)
• LogP: 2.50610
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 207.9152559
• Heavy Atom Count: 11
• Complexity: 175

Purity/Quality:

99%min ^*data from raw suppliers

Thiophene-3,4-dicarbonyldichloride 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=CS1)C(=O)Cl)C(=O)Cl

Technology Process of Thiophene-3,4-dicarbonyl dichloride

There total 11 articles about Thiophene-3,4-dicarbonyl dichloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

thiophene-3,4-dicarboxylic acid (4282-29-5) → thiophene-3,4-dicarboxylic acid chloride (33527-26-3)

Guidance literature:

With oxalyl dichloride; In N,N-dimethyl-formamide; toluene; at 111 ℃; for 2h; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.201602392

Reference yield:

3,4-dicyanothiophene (18853-32-2) → thiophene-3,4-dicarboxylic acid chloride (33527-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / KOH / ethane-1,2-diol / 4 h / Heating

2: thionyl chloride / 1 h / Heating

With potassium hydroxide; thionyl chloride; In ethylene glycol;

Reference yield:

diethyl thiophene-3,4-dicarboxylate (53229-47-3) → thiophene-3,4-dicarboxylic acid chloride (33527-26-3)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / ethanol / Heating

2: thionyl chloride / 1 h / Heating

With sodium hydroxide; thionyl chloride; In ethanol;

upstream raw materials:

thiophene-3,4-dicarboxylic acid

3,4-dicyanothiophene

diethyl thiophene-3,4-dicarboxylate

diethyl 2-formyl-3-(diethoxymethyl)succinate

Downstream raw materials:

4,9-Dihydronaphtho<2,3c>thiophen-4,9-dion

[4-(hydroxymethyl)-3-thienyl]methanol

Refernces

• 1、 Takeda, Youhei,Hatanaka, Kota,Nishida, Takuya,Minakata, Satoshi. "Thieno[3,4-c]phosphole-4,6-dione: A Versatile Building Block for Phosphorus-Containing Functional π-Conjugated Systems". supporting information. p. 10360 - 10364. Retrieved 2016/07/22.
• 2、 Braunecker, Wade A.,Owczarczyk, Zbyslaw R.,Garcia, Andres,Kopidakis, Nikos,Larsen, Ross E.,Hammond, Scott R.,Ginley, David S.,Olson, Dana C.. "Benzodithiophene and imide-based copolymers for photovoltaic applications". experimental part. p. 1346 - 1356. Retrieved 2012/08/28.