[2,2'-Bithiophene]-5,5'-dicarboxylic acid

Base Information

• Chemical Name: [2,2'-Bithiophene]-5,5'-dicarboxylic acid
• CAS No.: 3515-34-2
• Molecular Formula: C10H6 O4 S2
• Molecular Weight: 254.28
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20353742
• Nikkaji Number: J2.107.076I
• Wikidata: Q82131499
• Mol file: 3515-34-2.mol

Synonyms:3515-34-2;[2,2'-Bithiophene]-5,5'-dicarboxylic acid;[2,2'-Bithiophene]-5,5'-dicarboxylicacid;5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid;2,2'-BITHIOPHENE-5,5'-DICARBOXYLIC ACID;CBDivE_010512;Ammoniumfluoride;SCHEMBL593023;YSZC1256;DTXSID20353742;HMS1579D19;AKOS000122932;BS-51740;CS-0170578;2,2''-Bithiophene-5,5''-dicarboxylic acid;F74294;SR-01000201292;SR-01000201292-1

Chemical Property of [2,2'-Bithiophene]-5,5'-dicarboxylic acid

Chemical Property:

• Boiling Point: 538.7°Cat760mmHg
• Flash Point: 279.6°C
• PSA: 131.08000
• Density: 1.601g/cm³
• LogP: 2.87300
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 253.97075102
• Heavy Atom Count: 16
• Complexity: 277

Purity/Quality:

99%, ^*data from raw suppliers

2,2'-BITHIOPHENE-5,5'-DICARBOXYLIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(SC(=C1)C(=O)O)C2=CC=C(S2)C(=O)O

Technology Process of [2,2'-Bithiophene]-5,5'-dicarboxylic acid

There total 6 articles about [2,2'-Bithiophene]-5,5'-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: 70.8%

carbon dioxide (124-38-9,18923-20-1) + 2,2'-Bithiophene (492-97-7) → 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid (3515-34-2)

Guidance literature:

2,2'-Bithiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -70 ℃; for 4h; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; hexane; at -70 - 20 ℃; Inert atmosphere;

DOI:10.1134/S002247662011013X

Reference yield: 70.0%

5-bromothiophene-2-carboxylic acid (7311-63-9) + tris(3,5-dimethoxyphenyl)aluminum → 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid (3515-34-2) + C13H12O4S

Guidance literature:

With Co(1,10-phenanthroline)Cl₂; In tetrahydrofuran; for 6h; chemoselective reaction; Inert atmosphere; Reflux; Schlenk technique;

DOI:10.1039/d1cc04002b

Reference yield: 37.0%

2,2'-Bithiophene (492-97-7) → 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid (3515-34-2)

Guidance literature:

2,2'-Bithiophene; With n-butyllithium; In diethyl ether; hexane; at -78 ℃; for 2h; Inert atmosphere;

With carbon dioxide; In diethyl ether; hexane; at -78 - 20 ℃;

DOI:10.1039/c9nj06202e

upstream raw materials:

carbon dioxide

2,2'-Bithiophene

5,5'-dibromo-2,2'-bisthiophene

5-bromothiophene-2-carboxylic acid

Downstream raw materials:

5-(thien-2-yl)thiophene-2-carboxylic acid

N-{5-[5-(4-amidinophenoxycarbonyl)thiophen-2-yl]thiophen-2-ylcarbonyl}-L-aspartic acid trifluoroacetic acid salt

Refernces

• 1、 Dubskikh, V. A.,Dybtsev, D. N.,Fedin, V. P.,Lysova, A. A.,Ryadun, A. A.,Samsonenko, D. G.,Samsonov, V. A.. "STRUCTURE AND LUMINESCENT PROPERTIES OF COORDINATION POLYMERS CONTAINING LEAD(II) AND THIOPHENE LIGANDS". . p. 1800 - 1809. Retrieved 2020/12/28.
• 2、 Einkauf, Jeffrey D.,Ortega, Raul E.,Mathivathanan, Logesh,De Lill, Daniel T.. "Nitroaromatic sensing with a new lanthanide coordination polymer [Er2(C10H4O4S2)3(H2O)6]:N assembled by 2,2′-bithiophene-5,5′-dicarboxylate". supporting information. p. 10929 - 10934. Retrieved 2017/10/03.