2,5-Bis(trimethylstannyl)thiophene

Base Information

• Chemical Name: 2,5-Bis(trimethylstannyl)thiophene
• CAS No.: 86134-26-1
• Molecular Formula: C10H20SSn2
• Molecular Weight: 409.755
• European Community (EC) Number: 687-880-5
• DSSTox Substance ID: DTXSID70511198
• Wikidata: Q82369885
• Mol file: 86134-26-1.mol

Synonyms:2,5-Bis(trimethylstannyl)thiophene;86134-26-1;Stannane, 1,1'-(2,5-thiophenediyl)bis[1,1,1-trimethyl-;trimethyl-(5-trimethylstannylthiophen-2-yl)stannane;Stannane, 2,5-thiophenediylbis[trimethyl-;SCHEMBL572368;DTXSID70511198;KKRPPVXJVZKJON-UHFFFAOYSA-N;2,5-bis(trimethylstannyl)-thiophene;2,5-bis-trimethylstannanyl-thiophene;MFCD01940352;(Thiene-2,5-diyl)bis(trimethylstannane);2,5(c)\ bis(triMethylstannyl)th iophene;SY100706;2,5-Bis(trimethylstannyl)thiophene, 97%;D81152;A934283;TRIMETHYL[5-(TRIMETHYLSTANNYL)THIOPHEN-2-YL]STANNANE

Chemical Property of 2,5-Bis(trimethylstannyl)thiophene

Chemical Property:

• Melting Point: 93-102°C
• Boiling Point: 311.5±52.0 °C(Predicted)
• PSA: 32.09000
• LogP: 1.51720
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 409.93238
• Heavy Atom Count: 13
• Complexity: 158

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,5-Bis(trimethylstannyl)thiophene 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T,N
• Statements: 21-25-36/38-48/23/25-50/53
• Safety Statements: 35-36/37/39-45-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Sn](C)(C)C1=CC=C(S1)[Sn](C)(C)C

Technology Process of 2,5-Bis(trimethylstannyl)thiophene

There total 3 articles about 2,5-Bis(trimethylstannyl)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: 93.0%

thiophene (188290-36-0,8014-23-1,25233-34-5) + trimethyltin(IV)chloride (1066-45-1) → 2,5-bis-trimethylstannanyl-thiophene (86134-26-1)

Guidance literature:

thiophene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; at 0 ℃; for 0.916667h; Reflux;

trimethyltin(IV)chloride; In tetrahydrofuran; hexane; at 24 ℃; for 15h;

DOI:10.1021/ol302571t

Reference yield: 90.0%

(trimethylstannyl)lithium (17946-71-3) + 2,5-dibromothiophen (3141-27-3) → 2,5-bis-trimethylstannanyl-thiophene (86134-26-1)

Guidance literature:

In tetrahydrofuran; Sn-compd. soln. addn. dropwise to org, compd. soln. at 0°C, stirring overnight at room temp., solvent vac. evapn., residue extn. (n-hexane); solvent evapn., solid recrystn. (hexane); elem. anal.;

Reference yield: 83.0%

2,5-dibromothiophen (3141-27-3) + trimethyltin(IV)chloride (1066-45-1) → 2,5-bis-trimethylstannanyl-thiophene (86134-26-1)

Guidance literature:

2,5-dibromothiophen; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

trimethyltin(IV)chloride; In tetrahydrofuran; hexane; at 20 ℃; Inert atmosphere;

upstream raw materials:

(trimethylstannyl)lithium

2,5-dibromothiophen

thiophene

trimethyltin(IV)chloride

Downstream raw materials:

2,5-Diphenyl-thiophene

2,5-diiodothiophene

2-iodo-5-methylthiophene

2,5-bis(4-nitrophenyl)thiophene

Refernces

Synthesis and antiparasitic evaluation of bis-2,5-[4-guanidinophenyl]thiophenes

10.1016/j.ejmech.2006.11.006

The research focuses on the development and evaluation of a series of bis-2,5-[4-guanidinophenyl]thiophenes as potential antiparasitic agents. The researchers synthesized these compounds through a five-step process starting from 2,5-bis[trimethylstannyl]thiophene, involving Stille coupling, reduction, and subsequent reactions to introduce guanidino groups. Key chemicals used in the synthesis include 4-bromonitrobenzene, stannous chloride, ethyl isothiocyanatoformate, and various amines for N-alkyl and N-aryl substitutions. The synthesized compounds were evaluated for their DNA affinity and in vitro efficacy against Trypanosoma brucei rhodesiense (T. b. r.), Plasmodium falciparum (P. f.), Leishmania donovani (L. d.), and Trypanosoma cruzi (T. c.), as well as in vivo efficacy against T. b. r. in a mouse model. The results showed that certain compounds exhibited promising in vitro activity against T. b. r. and P. f., with some demonstrating superior in vivo activity against T. b. r. compared to existing drugs like pentamidine and furamidine. The study concludes that these bis-2,5-[4-guanidinophenyl]thiophenes merit further investigation as potential new treatments for parasitic diseases due to their strong DNA affinity and effective antiparasitic activity.