Thiophene-2,3-dicarboxylic acid

Base Information

• Chemical Name: Thiophene-2,3-dicarboxylic acid
• CAS No.: 1451-95-2
• Molecular Formula: C6H4O4S
• Molecular Weight: 172.161
• Hs Code.: 2934999090
• European Community (EC) Number: 820-356-8
• NSC Number: 81792
• UNII: 2V973J2YFE
• DSSTox Substance ID: DTXSID70292334
• Nikkaji Number: J802.991A
• Wikidata: Q82030604
• Mol file: 1451-95-2.mol

Synonyms:thiophene-2,3-dicarboxylic acid;1451-95-2;2,3-Thiophenedicarboxylic acid;Thiophene-2,3-dicarboxylicacid;thiophene dicarboxylic acid;NSC-81792;phenoperidinehydrochloride;SCHEMBL69159;2V973J2YFE;thiphene-2,3-dicarboxylic acid;DTXSID70292334;AMY18043;NSC81792;CCG-40466;GEO-02875;MFCD00034738;AKOS006237898;AS-60242;CS-0182734;FT-0697103;EN300-58883;AI-942/25034152;F2108-0183;Z877960192

Chemical Property of Thiophene-2,3-dicarboxylic acid

Chemical Property:

• Vapor Pressure: 0.206mmHg at 25°C
• Refractive Index: 1.666
• Boiling Point: 405.9 °C at 760 mmHg
• Flash Point: 199.3 °C
• PSA: 102.84000
• Density: 1.655 g/cm³
• LogP: 1.14450
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 171.98302978
• Heavy Atom Count: 11
• Complexity: 191

Purity/Quality:

98% ^*data from raw suppliers

Thiophene-2,3-dicarboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1C(=O)O)C(=O)O

Technology Process of Thiophene-2,3-dicarboxylic acid

There total 26 articles about Thiophene-2,3-dicarboxylic acid 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: 92.0%

2-(N-tert-butylcarbamoyl)thiophene-3-carboxylic acid (98331-03-4) → thiophene-2,3-dicarboxylic acid (1451-95-2)

Guidance literature:

With sulfuric acid; for 24h; Heating;

DOI:10.1021/jo00222a032

Reference yield: 92.0%

2-(3-carboxy-2-thienyl)-4,4-dimethyloxazoline (97759-73-4) → thiophene-2,3-dicarboxylic acid (1451-95-2)

Guidance literature:

With potassium hydroxide; sodium hypochlorite; tetra-tert-butylammonium hydrogen sulfate; 1.) ethyl acetate, water, 20 deg C, 12 h, 2.) water, MeOH, 20 deg C, 12 h;

Reference yield: 89.0%

3-bromothiophene-2-carboxylic acid (7311-64-0) + carbon dioxide (124-38-9,18923-20-1) → thiophene-2,3-dicarboxylic acid (1451-95-2)

Guidance literature:

3-bromothiophene-2-carboxylic acid; With n-butyllithium; In diethyl ether; at -78 ℃; for 0.166667h; Inert atmosphere;

carbon dioxide; In diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1039/c1cc14179a

upstream raw materials:

2-acetyl-3-methylthiophene

2-methylthiophene-3-carboxylic acid

2-thiophenylcarboxylic acid

carbon dioxide

Downstream raw materials:

thieno[3,4-b]thiophene

Refernces

• 1、 He. "Solvent evaporation method and crystal structure of thiophene-2,3-dicarboxylate". . p. 769 - 770. Retrieved 2015.
• 2、 Reinecke, Manfred G.,Newsom, James G.,Almqvist, K. Anders. "An Improved Synthesis of Thiophene-2,3-dicarboxylic Acid by Sequential Carboxylation". . p. 327 - 329. Retrieved 1980.
• 3、 Baumeister, S?ren,Schepmann, Dirk,Wünsch, Bernhard. "Thiophene bioisosteres of GluN2B selective NMDA receptor antagonists: Synthesis and pharmacological evaluation of [7]annuleno[b]thiophen-6-amines". . . Retrieved 2019/12/25.
• 4、 Postma, Tobias M.,Galloway, Warren R.J.D.,Cougnon, Fabien B. L.,Panto?, G. Dan,Stokes, Jamie E.,Spring, David R.. "Dynamic combinatorial chemistry with novel dithiol building blocks: Towards new structurally diverse and adaptive screening collections". supporting information. p. 765 - 769. Retrieved 2013/05/09.