2,5-Bis(trimethylstannyl)thieno[3,2-b]thiophene

Base Information

• Chemical Name: 2,5-Bis(trimethylstannyl)thieno[3,2-b]thiophene
• CAS No.: 469912-82-1
• Molecular Formula: C12H20S2Sn2
• Molecular Weight: 465.843
• European Community (EC) Number: 807-949-7
• Mol file: 469912-82-1.mol

Synonyms:469912-82-1;2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene;2,5-Bis(trimethylstannyl)-thieno[3,2-b]thiophene;MFCD22200503;trimethyl-(5-trimethylstannylthieno[3,2-b]thiophen-2-yl)stannane;2,5(c)\ bis(triMethylstannyl)th ieno[3,2(c)\b]thiophene;bis(triMethylstannyl)th;Stannane, thieno[3,2-b]thiophene-2,5-diylbis[trimethyl-;ieno[3,2-b]thiophene;SCHEMBL1278927;HDZULVYGCRXVNQ-UHFFFAOYSA-N;AMY18765;AKOS025401937;CS-W018456;AC-27448;SY035196;B4536;FT-0747441;F20562;2,5-bis-trimethylstannyl-thieno[3,2-b]thiophene;2,5-Bis-trimethylstannylthieno[3,2-b]thiophene;2,5-Bistrimethylstannyl-thieno[3,2-b]thiophene;2,5?Bis(Trimethylstannyl)th ieno[3,2?b]thiophene;J-507265;2,5-Bis(trimethylstannyl)-thieno[3,2-b]thiophene, 97%;2 pound not5-Bis(trimethylstannyl)thieno[3 pound not2-b]thiophene

Chemical Property of 2,5-Bis(trimethylstannyl)thieno[3,2-b]thiophene

Chemical Property:

• Melting Point: 127-132 °C
• Boiling Point: 383.8±52.0 °C(Predicted)
• PSA: 56.48000
• LogP: 4.05320
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 465.90445
• Heavy Atom Count: 16
• Complexity: 239

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): T+,N
• Hazard Codes: T+,N
• Statements: 26/27/28-50/53
• Safety Statements: 26-27-28-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Sn](C)(C)C1=CC2=C(S1)C=C(S2)[Sn](C)(C)C
• Description: 2,5-bis(trimethylstannyl)thieno[3,2-b]thiophene can be prepared by using thieno[3,2-b]thiophene?as starting material, further reaction with dibromo compounds (Stille Coupling) to form oligomers or polymers which can be used for organic electronic devices.
• Uses: 2,5-Bis(trimethylstannyl)-thieno[3,2-b]thiophene can be used as a copolymer in the synthesis of thiophene based materials for the fabrication of organic electronic devices such as organic field effect transistors (OFETs), organic thin film transistors(OTFTs) and organic photovoltaic cells (OPVs).

Technology Process of 2,5-Bis(trimethylstannyl)thieno[3,2-b]thiophene

There total 7 articles about 2,5-Bis(trimethylstannyl)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: 68.0%

thieno[3,2-b]thiophene (251-41-2) + trimethyltin(IV)chloride (1066-45-1) → trimethyl[5-(trimethylstannyl)thieno[3,2-b]thiophen-2-yl]stannane (469912-82-1)

Guidance literature:

thieno[3,2-b]thiophene; With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 4h;

trimethyltin(IV)chloride; In tetrahydrofuran; at -78 - 20 ℃; for 16.5h;

Reference yield: 66.0%

2,5-dibromothieno[3,2-b]thiophene (25121-87-3) + trimethyltin(IV)chloride (1066-45-1) → trimethyl[5-(trimethylstannyl)thieno[3,2-b]thiophen-2-yl]stannane (469912-82-1)

Guidance literature:

With n-butyl lithium; In diethyl ether; hexane; byproducts: LiBr; to a soln. of Br-compound in diethyl ether was added a soln. of BuLi in hexane at 0°C under Ar, after 10 min a soln. of (CH3)3SnCl in diethyl ether was added, stirred at 0°C for 105 min; poured into water, etxd. with diethyl ether, dried over MgSO4, evapd., the residue was dissolved in benzene, treated with activated carbon, evapd., recrystd. from ehanol; elem. anal.;

DOI:10.1016/S0022-328X(02)01375-X

Reference yield:

3-bromo-2-thiophenecarboxaldehyde (930-96-1) → trimethyl[5-(trimethylstannyl)thieno[3,2-b]thiophen-2-yl]stannane (469912-82-1)

Guidance literature:

Multi-step reaction with 5 steps

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

2: sodium hydroxide / tetrahydrofuran

3: copper; hydrogenchloride; quinoline

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

5: n-butyllithium / tetrahydrofuran

With quinoline; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; copper; potassium carbonate; sodium hydroxide; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

trimethyltin(IV)chloride

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

thieno[3,2-b]thiophene

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

Downstream raw materials:

2,5-bis(3-hexylthiophen-2-yl)thieno[3,2-b]thiophene