2,5-Di(thiophen-2-yl)thieno[3,2-b]thiophene

Base Information

• Chemical Name: 2,5-Di(thiophen-2-yl)thieno[3,2-b]thiophene
• CAS No.: 21210-90-2
• Molecular Formula: C₁₄H₈S₄
• Molecular Weight: 304.482
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60471499
• Nikkaji Number: J1.988.790A
• Wikidata: Q82300016
• Mol file: 21210-90-2.mol

Synonyms:2,5-Di(thiophen-2-yl)thieno[3,2-b]thiophene;21210-90-2;2,5-Di(2-thienyl)thieno[3,2-b]thiophene;2,5-dithiophen-2-ylthieno[3,2-b]thiophene;2,5-Di-thiophen-2-yl-thieno[3,2-b]thiophene;SCHEMBL12921576;DTXSID60471499;MFCD11114556;AKOS015856673;AS-77098;CS-0179373;D4725;T70561;2,5-di(thiophen-2-yl)thieno [3,2-b]thiophene

Chemical Property of 2,5-Di(thiophen-2-yl)thieno[3,2-b]thiophene

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 258-259 °C
• Boiling Point: 486°C at 760 mmHg
• Flash Point: 187.504°C
• PSA: 112.96000
• Density: 1.436g/cm³
• LogP: 6.41980
• Storage Temp.: 2-8°C
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 303.95088495
• Heavy Atom Count: 18
• Complexity: 278

Purity/Quality:

97% ^*data from raw suppliers

2,5-Di(2-thienyl)thieno[3,2-b]thiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC(=C1)C2=CC3=C(S2)C=C(S3)C4=CC=CS4
• Uses: 2,5-Di(2-thienyl)thieno[3,2-b]thiophene is a useful intermediate for the preparation of thieno[3,2-b]thiophene derivatives used as semiconductor materials.

Technology Process of 2,5-Di(thiophen-2-yl)thieno[3,2-b]thiophene

There total 6 articles about 2,5-Di(thiophen-2-yl)thieno[3,2-b]thiophene 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: 72.0%

2,5-dibromothieno[3,2-b]thiophene (25121-87-3) + 2-thiopheneboronic acid pinacol ester (193978-23-3) → 2,5-di-thiophen-2-yl-thieno[3,2-b]thiophene (21210-90-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate; In tetrahydrofuran; water; for 60h; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1039/c7ra01793f

Reference yield: 63.0%

2,5-dibromothieno[3,2-b]thiophene (25121-87-3) + tributyl(thien-2-yl)stannane (54663-78-4) → 2,5-di-thiophen-2-yl-thieno[3,2-b]thiophene (21210-90-2)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 90 ℃; Schlenk technique; Inert atmosphere;

DOI:10.3390/molecules171012163

Reference yield:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → 2,5-di-thiophen-2-yl-thieno[3,2-b]thiophene (21210-90-2)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium carbonate / N,N-dimethyl-formamide

2: sodium hydroxide

3: copper; quinoline

4: N-Bromosuccinimide / N,N-dimethyl-formamide

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 90 °C / Schlenk technique; Inert atmosphere

With quinoline; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper; potassium carbonate; sodium hydroxide; In N,N-dimethyl-formamide;

DOI:10.3390/molecules171012163

upstream raw materials:

2,5-dibromothieno[3,2-b]thiophene

tributyl(thien-2-yl)stannane

3-bromo-2-thiophenecarboxaldehyde

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