63574-85-6

Usage

Uses

Used in Electronic Materials Industry:
2,5-bis(4-bromophenyl)thiophene is used as a building block for the synthesis of new electronic materials, such as organic semiconductors and conductive polymers, due to its bromine substituents that allow for further functionalization and modification of the compound.
Used in Material Science Research:
2,5-bis(4-bromophenyl)thiophene is used as a research compound in material science to explore its properties and potential applications in the development of advanced materials with tailored electronic, optical, or mechanical properties.
Used in Organic Synthesis:
2,5-bis(4-bromophenyl)thiophene is used as an intermediate in the synthesis of various organic compounds, taking advantage of the reactivity of its bromine substituents for further chemical reactions and transformations.

Synthetic route

1,4-bis(4-bromophenyl)-1,4-butanedione (2461-83-8) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6)

Conditions	Yield
With Lawessons reagent; 1,1,1,3',3',3'-hexafluoro-propanol for 18h; Paal-Knorr Pyrrole Synthesis; Inert atmosphere; Reflux;	83%
With hydrogenchloride; chloroform; hydrogen sulfide; tin(IV) chloride

2,5-bis(4-trimethylsilylphenyl)thiophene (141775-93-1) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6)

Conditions	Yield
With N-Bromosuccinimide In tetrahydrofuran; acetic acid at 60℃; for 0.5h;	82%

1,4-bis(4-bromodiphenyl)buta-1,3-diyne (959-88-6) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6)

Conditions	Yield
With sulfur; sodium t-butanolate In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere; Schlenk technique;	63%

1,4-bis(4-bromodiphenyl)buta-1,3-diyne (959-88-6) + sodium triisopropylsilanethiolate → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6) + 2,5-bis(4-bromophenyl)-3-(triisopropylsilyl)thiophene (1426938-85-3)

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; for 1h; Schlenk technique; Inert atmosphere;	A 46% B 53%

1-(4'-bromophenyl)-2-{5-[(2-(4-bromophenyl)-2-oxoethyl)sulfanyl]-2-thioxo-1,3-dithiol-4-ylsulfanyl}ethanone (337533-82-1) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6) + 6-(4-bromophenyl)thieno[2,3-d][1,3]dithiole-2-thione (625851-29-8) + 5-(4'-bromophenyl)-[1,3]dithiolo[4,5-b][1,4]dithiin-2-thione (337533-83-2)

Conditions	Yield
With tetraphosphorus decasulfide In toluene Heating;	A 10% B 2% C 40%

para-bromoacetophenone (99-90-1) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6) + 7-(4-bromophenyl)-2,4,6,8,9-pentathia-1,3,5-triphosphaadamantane-1,3,5-trisulfide

Conditions	Yield
With tetraphosphorus decasulfide In benzene for 20h; Reflux;	A 16% B 32%

1.4-dibromobenzene (106-37-6) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6)

Conditions

Yield

Multi-step reaction with 3 steps 1.1: n-BuLi / diethyl ether / 1 h / -10 °C 1.2: 90 percent / diethyl ether / 1 h / -10 - 20 °C 2.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / diethyl ether / 1 h / -65 °C 2.2: ZnCl2 / diethyl ether; tetrahydrofuran / 1 h / 25 °C 2.3: 32 percent / Pd(PPh3)4 / diethyl ether; tetrahydrofuran / 7 h / 50 °C 3.1: 82 percent / NBS / tetrahydrofuran; acetic acid / 0.5 h / 60 °C View Scheme

1-bromo-4-(trimethylsilyl)benzene (6999-03-7) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / diethyl ether / 1 h / -65 °C 1.2: ZnCl2 / diethyl ether; tetrahydrofuran / 1 h / 25 °C 1.3: 32 percent / Pd(PPh3)4 / diethyl ether; tetrahydrofuran / 7 h / 50 °C 2.1: 82 percent / NBS / tetrahydrofuran; acetic acid / 0.5 h / 60 °C View Scheme

para-bromoacetophenone (99-90-1) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) chloride; triethylamine; ethanol / toluene / 168 h / 20 °C / Inert atmosphere 2: Lawessons reagent; 1,1,1,3',3',3'-hexafluoro-propanol / 18 h / Inert atmosphere; Reflux View Scheme

para-bromophenacyl bromide (99-73-0) → 2,5-Bis(p-bromophenyl)thiophene (63574-85-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: zinc(II) chloride; triethylamine; ethanol / toluene / 168 h / 20 °C / Inert atmosphere 2: Lawessons reagent; 1,1,1,3',3',3'-hexafluoro-propanol / 18 h / Inert atmosphere; Reflux View Scheme

2,5-Bis(p-bromophenyl)thiophene (63574-85-6) + bis(pinacol)diborane (73183-34-3) → 2,5-bis(4-pinacolborylphenyl)thiophene

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In toluene at 90℃; for 24h; Miyaura Borylation Reaction; Inert atmosphere;	89.1%

2,5-Bis(p-bromophenyl)thiophene (63574-85-6) + 2-phenylthiophen-5-ylboronic acid (306934-95-2) → 2,5-bis[4-(5'-phenylthiophen-2'-yl)phenyl]thiophene

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In various solvent(s) at 80℃; for 8h; Suzuki coupling reaction;	15%

2,5-Bis(p-bromophenyl)thiophene (63574-85-6) → 2, 5-bis(4-aminophenyl)thiophene (70010-49-0)

Conditions	Yield
With ammonium hydroxide; copper(I) bromide at 230℃;

2,5-Bis(p-bromophenyl)thiophene (63574-85-6) → 3,4-dibromo-2,5-bis-(4-bromo-phenyl)-thiophene

Conditions	Yield
With chloroform; bromine

2,5-Bis(p-bromophenyl)thiophene (63574-85-6) + 1-(tri-n-butylstannyl)-4-n-hexylbenzene → 2,5-bis[4(4'-n-hexylphenyl)phenyl]thiophene (56316-92-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 90℃;

Upstream product

• 2461-83-8 1,4-bis(4-bromophenyl)-1,4-butanedione 
• 141775-93-1 2,5-bis(4-trimethylsilylphenyl)thiophene 
• 99-73-0 para-bromophenacyl bromide 
• 99-90-1 para-bromoacetophenone 
• 959-88-6 1,4-bis(4-bromodiphenyl)buta-1,3-diyne 
• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 
• 106-37-6 1.4-dibromobenzene 
• 337533-82-1 1-(4'-bromophenyl)-2-{5-[(2-(4-bromophenyl)-2-oxoethyl)sulfanyl]-2-thioxo-1,3-dithiol-4-ylsulfanyl}ethanone 

Downstream Products

• 70010-49-0 2, 5-bis(4-aminophenyl)thiophene 
• 56316-92-8 2,5-bis[4(4'-n-hexylphenyl)phenyl]thiophene 

Relevant academic research and scientific papers

Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles

An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles.

Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon

The synthesis of novel adamantane-like cage compounds consisting of phosphorus, sulfur, and carbon atoms was developed. We examined the reaction of a variety of acetophenone derivatives with P4S10 in refluxing benzene. A novel noradamantane-like cage compound was also synthesized, when the reaction of 2’-methoxyacetophenone with P4S10 was performed in refluxing toluene. In addition, by using the adamantane-like cage compound, 4,4’-dimethoxybenzophenone and N,N-dimethylbenzamide were successfully transformed into the corresponding thioketone (98%) and benzothioamide (89%), respectively.

Trisulfur radical anion as the key intermediate for the synthesis of thiophene via the interaction between elemental sulfur and NaO t Bu

A facile base-promoted sulfur-centered radical generation mode and a single-step protocol for the synthesis of thiophene derivatives using 1,3-diynes via the interaction between elemental sulfur and NaOtBu has been reported. EPR experiments revealed that the trisulfur radical anion acts as a key intermediate of this process. A plausible mechanism has been proposed.

Sulfur heterocyclization and 1,3-migration of silicon in reaction of 1,3-diynes with sodium triisopropylsilanethiolate: One-pot synthesis of 2,5-disubstituted 3-(triisopropylsilyl)thiophenes

Sulfur heterocyclization and 1,3-migration of silicon have been realized in the reactions of a range of 1,3-diynes with sodium triisopropylsilanethiolate in N,N-dimethylformamide. These provided 40-72% yields of 2,5-disubstituted 3-(triisopropylsilyl)thiophenes and up to 50% yield of 2,5-disubstituted thiophenes. Georg Thieme Verlag Stuttgart, New York.

Synthesis of Thiophene/phenylene Co-oligomers. IV [1]. 6- to 8-Ring Molecules

We report the synthesis of various thiophene/phenylene co-oligomers with total number of thiophene and benzene (phenylene) rings of 6 to 8. These compounds include a phenyl-capped sexithiophene, a thienyl-capped quaterphenylene, as well as block and alternating co-oligomers. The synthesis is based on either the Suzuki coupling reaction or the direct dimerization coupling. The latter method produces symmetric molecules with an even total ring number. These reaction schemes enables us to obtain the target compounds in high quality. Although the resulting materials are difficult to dissolve in organic solvents and therefore difficult to identify by usual 1H nmr spectroscopy, they have successfully been identified through Fourier-transform ir spectroscopy. The specific group frequencies of ring-stretching and out-of plane deformation modes are characteristic of the substitution pattern of the individual thiophene and benzene rings.

An in depth study of the formation of new tetrathiafulvalene derivatives from 1,8-diketones

A detailed study of the reactions of phosphorus pentasulfide and Lawesson's reagent with a series of 4,5-bis(RCOCH 2S)-1,3-dithiole-2-thiones (R=Ph, 4-MeOC6H4, 4-Br C6H4, Me) has been carried out. These reactions lead to fusion of either an unsaturated 1,4-dithiin ring or a thiophene to the dithiole; the former in higher yield, while the latter is a significant product in the reactions with Lawesson's reagent; as well as small amounts of minor products. A mechanistic rationalization of these products is discussed in some detail. The new fused dithioles have been converted to novel series of fused TTF derivatives.