Thieno[2,3-b]thiophene-2-carboxylic acid

Base Information

• Chemical Name: Thieno[2,3-b]thiophene-2-carboxylic acid
• CAS No.: 14756-75-3
• Molecular Formula: C7H4O2S2
• Molecular Weight: 184.24
• Hs Code.: 2934999090
• European Community (EC) Number: 692-051-6
• DSSTox Substance ID: DTXSID10372321
• Wikidata: Q72508456
• Mol file: 14756-75-3.mol

Synonyms:thieno[2,3-b]thiophene-2-carboxylic acid;14756-75-3;thieno[2,3-b]thiophene-5-carboxylic acid;Thieno[2,3-b] thiophene-2-carboxylic acid;Thieno[2,3-b]thiophene-2-carboxylicacid;SCHEMBL1761579;DTXSID10372321;JXHSGSLIUHNKRC-UHFFFAOYSA-N;MFCD00111552;AKOS006229467;BS-49278;CS-0217179;FT-0758653;E78347;EN300-702736;A884422;J-524928;thieno[2,3-b]thiophene-2-carboxylic acid, AldrichCPR;Z1198150636;2-CHLORO-4-(METHYLSULFONYL)-OXO-1-CYCLOHEXEN-1-YLBENZOICACID

Chemical Property of Thieno[2,3-b]thiophene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 236 °C
• Refractive Index: 1.77
• Boiling Point: 389.495 °C at 760 mmHg
• PKA: 3.41±0.30(Predicted)
• Flash Point: 189.36 °C
• PSA: 93.78000
• Density: 1.602 g/cm³
• LogP: 2.66100
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 183.96527171
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

98%min ^*data from raw suppliers

Thieno[2,3-b]thiophene-2-carboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC2=C1C=C(S2)C(=O)O

Technology Process of Thieno[2,3-b]thiophene-2-carboxylic acid

There total 7 articles about Thieno[2,3-b]thiophene-2-carboxylic 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: 100.0%

methyl thieno[2,3-b]thiophene-2-carboxylate (20969-37-3) → thieno<2,3-b>thiophene-2-carboxylic acid (14756-75-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; for 24h;

DOI:10.1021/jm980722p

Reference yield:

3-thiophene carboxaldehyde (498-62-4) → thieno<2,3-b>thiophene-2-carboxylic acid (14756-75-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene-4-sulfonic acid / toluene / 6 h / 165 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 °C / Schlenk technique; Inert atmosphere

2.2: 1 h / 25 °C / Schlenk technique; Inert atmosphere

2.3: 2 h / 25 °C / Schlenk technique; Inert atmosphere

3.1: toluene-4-sulfonic acid / acetone / 1 h / 25 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C

5.1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C

With n-butyllithium; water; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene;

DOI:10.1039/c9ob00487d

Reference yield:

2-(thiophen-3-yl)-1,3-dioxolane (13250-82-3) → thieno<2,3-b>thiophene-2-carboxylic acid (14756-75-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 °C / Schlenk technique; Inert atmosphere

1.2: 1 h / 25 °C / Schlenk technique; Inert atmosphere

1.3: 2 h / 25 °C / Schlenk technique; Inert atmosphere

2.1: toluene-4-sulfonic acid / acetone / 1 h / 25 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C

4.1: lithium hydroxide; water / tetrahydrofuran / 4 h / 100 °C

With n-butyllithium; water; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hydroxide; In tetrahydrofuran; hexane; dichloromethane; acetone;

DOI:10.1039/c9ob00487d

upstream raw materials:

2-(1-oxoethyl)thieno<2,3-b>thiophene

methyl thieno[2,3-b]thiophene-2-carboxylate

3-thiophene carboxaldehyde

2-(thiophen-3-yl)-1,3-dioxolane

Downstream raw materials:

4-(2-{5-[(S)-2-(3-Benzyl-ureido)-2-methoxycarbonyl-ethylcarbamoyl]-thieno[2,3-b]thiophen-2-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester

4-{2-[5-(2-benzenesulfonylamino-2-carboxy-ethylcarbamoyl)-thieno[2,3-b]thiophen-2-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Egbertson, Melissa S.,Cook, Jacquelynn J.,Bednar, Bohumil,Prugh, John D.,Bednar, Rodney A.,Gaul, Stanley L.,Gould, Robert J.,Hartman, George D.,Homnick, Carl F.,Holahan, Marie A.,Libby, Laura A.,Lynch Jr., Joseph J.,Lynch, Robert J.,Sitko, Gary R.,Stranieri, Maria T.,Vassallo, Laura M.. "Non-peptide GPIIb/IIIa inhibitors. 20. Centrally constrained thienothiophene α-sulfonamides are potent, long acting in vivo inhibitors of platelet aggregation". . p. 2409 - 2421. Retrieved 2007/10/03.