Production Method 1

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  24 h, rt

Reference

Effect of End-capping Functional Groups on the Optoelectronic Properties of Oligothiophene Derivatives

Zuo, Zhenyu; Sun, Hongjian; Li, Xiaoyan, Chinese Journal of Chemistry, 2012, 30(10), 2401-2410

Production Method 2

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  24 h, rt

Reference

Solvent Mixture Induced Self Assembly of a Terthiophene Based Rod-Coil Block Co-oligomer

Deepak, V. D.; Sundararajan, Pudupadi R., Journal of Physical Chemistry B, 2011, 115(26), 8458-8464

Production Method 3

3480-11-3

3141-27-3

94581-95-0

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ;  -78 °C
1.2 Reagents: Indium trichloride ;  -78 °C → rt
1.3 Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: Tetrahydrofuran ;  12 h, 80 °C

Reference

Synthesis of functionalized thiophenes and oligothiophenes by selective and iterative cross-coupling reactions using indium organometallics

Montserrat Martinez, M.; Pena-Lopez, Miguel; Sestelo, Jose Perez; Sarandeses, Luis A., Organic & Biomolecular Chemistry, 2012, 10(19), 3892-3898

Production Method 4

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  24 h, rt

Reference

Non-symmetrical oligothiophenes with 'incompatible' substituents

Didier, Delphine; Sergeyev, Sergey; Geerts, Yves Henri, Tetrahedron, 2007, 63(4), 941-946

Production Method 5

161726-69-8

94581-95-0

Reaction Conditions

1.1 Catalysts: Potassium tert-butoxide Solvents: Tetrahydrofuran

Reference

Base-promoted decarbonylation of bithiophene and terthiophene aldehydes

Mohanakrishnan, A. K.; Lakshmikantham, M. V.; Cava, M. P., Sulfur Letters, 1998, 21(6), 247-252

Production Method 6

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Chloroform ;  2 min, rt; 2.5 h, 0 °C

Reference

Mechanistic Insight into Thiophene Catalyst-Transfer Polymerization Mediated by Nickel Diimine Catalysts

Leone, Amanda K.; Souther, Kendra D.; Vitek, Andrew K.; LaPointe, Anne M.; Coates, Geoffrey W. ; et al, Macromolecules (Washington, 2017, 50(23), 9121-9127

Production Method 7

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide

Reference

3D-Hybrid networks with controllable electrical conductivity from the electrochemical deposition of terthiophene-functionalized polyphenylene dendrimers

John, Hermann; Bauer, Roland; Espindola, Pamela; Sonar, Prashant; Heinze, Juergen; et al, Angewandte Chemie, 2005, 44(16), 2447-2451

Production Method 8

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  5 h, -20 °C; 90 min, -20 °C; 14 h, rt

Reference

Fluorescent nucleoside analogs and combinatorial fluorophore arrays comprising same

, World Intellectual Property Organization, , ,

Production Method 9

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Acetic acid ,  Chloroform ;  16 h, rt

Reference

Preparation of thiophene compounds as antiinflammatory and antitumor agents

, United States, , ,

Production Method 10

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide ;  -20 °C; 20 h, -20 °C

Reference

Toward the Rational Design of Conjugated Oligomers and Polymers: Systematic Study of the Substituent Effect in Oligothiophenes

Zamoshchik, Natalia; Sheynin, Yana; Bendikov, Michael, Israel Journal of Chemistry, 2014, 54(5-6), 723-735

Production Method 11

1081-34-1

94581-95-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Solvents: Dimethylformamide

Reference

Solution-Phase Microwave-Assisted Synthesis of Unsubstituted and Modified α-Quinque- and Sexithiophenes

Melucci, M.; Barbarella, G.; Zambianchi, M.; Di Pietro, P.; Bongini, A., Journal of Organic Chemistry, 2004, 69(14), 4821-4828

Production Method 12

94581-95-0

Reaction Conditions

Reference

Novel nucleoside analogues with fluorophores replacing the DNA base

Strassler, Christoph; Davis, Newton E.; Kool, Eric T., Helvetica Chimica Acta, 1999, 82(12), 2160-2171

Production Method 13

94581-95-0

Reaction Conditions

Reference

Preparation of thiophene derivatives as immunostimulants

, United States, , ,

Production Method 14

94581-95-0

Reaction Conditions

Reference

Preparation of thiophene derivatives as drugs

, United States, , ,

Production Method 15

94581-95-0

Reaction Conditions

Reference

thiophene compounds as antivirus, antiinflammatory, and immunoregulatory agents

, Japan, , ,

Production Method 16

94581-95-0

Reaction Conditions

Reference

Selective synthesis of α-substituted oligothiophenes

Baauerle, Peter; Wuerthner, Frank; Goetz, Gunther; Effenberger, Franz, Synthesis, 1993, (11), 1099-103

Production Method 17

94581-95-0

Reaction Conditions

Reference

Preparation of terthienyls and analogs as phototoxic insecticides

, United States, , ,

Production Method 18

94581-95-0

Reaction Conditions

Reference

Selective and efficient syntheses of phototoxic 2,2':5',2''-terthiophene derivatives bearing a functional substituent in the 3'- or the 5-position

Rossi, Renzo; Carpita, Adriano; Ciofalo, Maurizio; Lippolis, Vito, Tetrahedron, 1991, 47(39), 8443-60

Production Method 19

1081-34-1

94581-95-0

98057-08-0

Reaction Conditions

1.1 Reagents: 2,4,5-Trichloro-3(2H)-pyridazinone Catalysts: Iron chloride (FeCl3) Solvents: Dichloromethane ;  10 min, rt

Reference

Rapid and effective multihalogenations of 2,2',5',2''-terthiophene with 2-halo-4,5-dichloropyridazin-3(2H)-ones under ambient conditions

Kim, Eun Jung; Jung, Kwang-Ju; Lee, In-Hye; Kim, Bo Ram; Kim, Jeum-Jong; et al, Bulletin of the Korean Chemical Society, 2010, 31(10), 2985-2988

Production Method 20

1081-34-1

94581-95-0

98057-08-0

Reaction Conditions

1.1R:Bromosuccinimide, S:CHCl3, S:AcOH

Reference

Preparation of α-quater-, α-sexi-, and α-octithiophenes

By Nakayama, Juzo et al, Heterocycles, 1987, 26(7), 1793-6

2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene Raw materials

• 5-Bromo-2,2-bithiophene 96%
• 2,2':5',2''-Terthiophene
• 2,5-Dibromothiophene
• 5''-Bromo-2,2':5',2''-terthiophene-5-carbaldehyde

2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene Preparation Products

• 2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene (94581-95-0)
• 5,5''-Dibromo-2,2':5',2''-terthiophene (98057-08-0)

• 1. Exclusive self-aligned β-phase PVDF films with abnormal piezoelectric coefficient prepared via phase inversion?
  N. Soin,D. Boyer,K. Prashanthi,S. Sharma,A. A. Narasimulu,J. Luo,T. H. Shah,E. Siores,T. Thundat Chem. Commun., 2015,51, 8257-8260
• 2. Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France)
  Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
• 3. Exceptional activity of sub-nm Pt clusters on CdS for photocatalytic hydrogen production: a combined experimental and first-principles study?
  Qiyuan Wu,Shangmin Xiong,Peichuan Shen,Shen Zhao,Alexander Orlov Catal. Sci. Technol., 2015,5, 2059-2064
• 4. Elusive 2-aminofuran Diels–Alder substrates for a straightforward synthesis of polysubstituted anilines?
  Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555
• 5. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341

Professional Introduction to 2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene (CAS No. 94581-95-0)

2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene, identified by the CAS number 94581-95-0, is a significant compound in the field of organic synthesis and pharmaceutical research. This molecule, featuring a unique thiophene core structure, has garnered considerable attention due to its potential applications in the development of advanced materials and bioactive molecules.

The structural composition of 2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene consists of a central thiophene ring substituted with a bromine atom at the 2-position and a bifurcated thiophene-thiophene unit at the 5-position. This distinctive arrangement imparts unique electronic and steric properties, making it a valuable intermediate in synthetic chemistry. The presence of multiple aromatic rings enhances its reactivity, allowing for further functionalization and derivatization, which is crucial for pharmaceutical applications.

In recent years, there has been growing interest in thiophene-based compounds due to their diverse biological activities and potential in medicinal chemistry. Research has demonstrated that thiophenes can exhibit antimicrobial, anti-inflammatory, and anticancer properties, depending on their structural modifications. The compound 2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene is no exception, and its unique structure suggests promising applications in drug discovery.

One of the most compelling aspects of 2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene is its role as a building block in the synthesis of more complex molecules. The bromine substituent at the 2-position provides a reactive site for cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, which are widely used in constructing biaryl structures. These types of reactions are fundamental in the preparation of many pharmaceuticals and agrochemicals.

The bifurcated thiophene unit at the 5-position adds an additional layer of complexity and functionality to the molecule. This feature allows for the creation of polycyclic systems that can mimic natural products or bioactive scaffolds. Such systems are often investigated for their potential to interact with biological targets, leading to novel therapeutic agents.

Recent studies have highlighted the importance of thiophene derivatives in developing organic electronic materials. The conjugated system inherent in thiophenes contributes to their semiconducting properties, making them suitable for use in organic light-emitting diodes (OLEDs), organic photovoltaics (OPVs), and field-effect transistors (OFETs). The compound 2-bromo-5-(5-thiophen-2-ylthiophen-2-yl)thiophene, with its extended π-conjugation, could be particularly useful in these applications.

The synthesis of 2-bromo-5-(5-thiophen-2-ylthiophen-2-yll)thiophene involves multi-step organic transformations that showcase the ingenuity of synthetic chemists. The process typically begins with the preparation of monosubstituted thiophenes, followed by sequential functionalization to introduce the bromine atom and the bifurcated thiophene unit. Advanced techniques such as palladium-catalyzed cross-coupling reactions are often employed to achieve these transformations with high selectivity and yield.

The versatility of 2-bromo-5-(5-thiophen-2-yllthiophen)-2-yll)thiop h ene extends beyond its role as a synthetic intermediate. Its unique structural features make it a candidate for further investigation as a lead compound in drug discovery programs. By leveraging computational methods and high-throughput screening, researchers can rapidly assess its biological activity against various targets. This approach accelerates the identification of novel therapeutic candidates and reduces the time-to-market for new drugs.

In conclusion, 2-bromo--(bromothieno[3',4':4',3']thieno[3',4']thieno[3'] thiop h ene) is a multifaceted compound with significant potential in both synthetic chemistry and pharmaceutical research. Its structural features enable diverse applications, from advanced material science to drug development. As research continues to uncover new methodologies and applications for thiophene derivatives, compounds like this are poised to play an increasingly important role in addressing global challenges in medicine and technology.

• 4805-22-5(5,5’-Dibromo-2,2-bithiophene)
• 647835-93-6(2,2':5',2'':5'',2''':5''',2'''':5'''',2'''''-Sexithiophene, 5,5'''''-dibromo-)
• 3480-11-3(5-Bromo-2,2-bithiophene 96%)
• 651329-41-8(Thiophene, 2,2'-[5-(2-thienyl)-1,3-phenylene]bis[5-bromo-)
• 146796-00-1(2,2'-Bithiophene, 5-bromo-5'-methyl-)
• 110046-60-1(5'-Bromo-2,2'-bithiophene-5-carbaldehyde)
• 29488-24-2(2-Bromo-5-phenylthiophene)
• 106925-97-7(2,2'-Bithiophene, 5-bromo-5'-phenyl-)
• 144153-60-6(2,2':5',2'':5'',2''':5''',2''''-Quinquethiophene, 5,5''''-dibromo-)
• 98057-08-0(5,5''-Dibromo-2,2':5',2''-terthiophene)