3480-11-3

Basic information

• Product Name: 5-BROMO-2 2'-BITHIOPHENE 96
• Synonyms: 5-BROMO-2 2'-BITHIOPHENE 96;5-Bromo-[2,2']bithiophenyl;5-BroMo-2,2'-bithiophene 96%;5-Bromo-alpha-dithienyl
• CAS NO: 3480-11-3
• Molecular Formula: C₈H₅BrS₂
• Molecular Weight: 245.16
• Product Categories: Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks;Building Blocks;C7 to C9;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 3480-11-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 29-32 °C(lit.)
• Boiling Point: 286 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.635 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 5-BROMO-2 2'-BITHIOPHENE 96(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2 2'-BITHIOPHENE 96(3480-11-3)
• EPA Substance Registry System: 5-BROMO-2 2'-BITHIOPHENE 96(3480-11-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 3480-11-3(Hazardous Substances Data)

Usage

Description

5-BROMO-2 2'-BITHIOPHENE 96 is an organic compound that consists of a bithiophene molecule with a bromine atom attached at the 5-position. It is a versatile building block in the synthesis of various organic compounds and materials.

Uses

Used in Organic Synthesis:
5-BROMO-2 2'-BITHIOPHENE 96 is used as a synthetic intermediate for the preparation of various organic compounds and materials. Its unique structure allows for the formation of new chemical bonds and the creation of novel molecules with potential applications in various fields.
Used in the Synthesis of Trimethyl-[2,2′;5′,2″;5″,2″]quaterthiophen-5-yl-silane (4TTMS):
5-BROMO-2 2'-BITHIOPHENE 96 is used as a key building block in the synthesis of 4TTMS, a quaterthiophene-based compound with potential applications in organic electronics, such as organic solar cells and organic field-effect transistors. The bromine atom in 5-BROMO-2 2'-BITHIOPHENE 96 can be replaced with other functional groups to modify the properties of the resulting 4TTMS compound.
5-BROMO-2 2'-BITHIOPHENE 96 is also used in the synthesis of 5-hexylsulfanyl-2,2′:5′,2′′-terthiophene, a terthiophene-based compound with potential applications in organic light-emitting diodes (OLEDs) and other optoelectronic devices. The introduction of the hexylsulfanyl group enhances the solubility and processability of the terthiophene compound, making it suitable for use in device fabrication.

Upstream product

• 110-86-1 pyridine 
• 1003-09-4 2-bromothiophene 
• 3141-27-3 2,5-dibromothiophen 
• 5713-61-1 thiophen-2-yl magnesium bromide 
• 492-97-7 2,2'-Bithiophene 
• 6165-68-0 thiophene boronic acid 
• 4805-22-5 5,5'-dibromo-2,2'-bisthiophene 

Downstream Products

• 151271-42-0 2-hexyl-5-(5-(thiophen-2-yl)thiophen-2-yl)thiophene 
• 327630-34-2 5-Perfluorohexyl-2,2'-dithiophene 
• 316127-65-8 8-([2,2'-bithiophen]-5-ylethynyl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran 
• 474787-51-4 4-(2-[2,2']bithienyl-5-ylvinyl)benzaldehyde 
• 492-97-7 2,2'-Bithiophene 
• 371149-37-0 5-piperidino-2,2'-bithiophene 
• 132898-95-4 2,2'-bithiophene-5-boronic acid 
• 256342-40-2 5-phenyl-2,2':5',2''-terthiophene 
• 259801-05-3 (1S)-1,4-anhydro-1,2-dideoxy-1-([2,2':5',2''-terthiophen]-5-yl)-3,5-di-O-(p-toluoyl)-D-erythro-pentitol 
• 259801-07-5 (1S)-1,4-anhydro-1,2-dideoxy-5-O-(4,4'-dimethoxytrityl)-1-([2,2':5',2''-terthiophen]-5-yl)-D-erythro-pentitol 
• 151271-43-1 α,ω-Dihexylsexithiophene 
• 113728-71-5 2,2':5',2'':5'',2''':5''',2'''':5'''',2''''':5''''',2'''''':5'''''',2'''''''-octithiophene 
• 479719-88-5 2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 7342-41-8 2,2':5',2''-terthiophene-5-carboxaldehyde 

Relevant articles and documents

PREPARATION OF α-QUATER-, α-SEXI, AND α-OCTITHIOPHENES

α-Quaterthiophene (1), α-sexithiophene (2), and α-octithiophene (3) (the highest member of α-oligothiophenes ever synthesized) were prepared from α-bithiophene, α-terthiophene, and α-quaterthiophene, respectively, via monobromination with N-bromosuccinimide followed by reductive coupling reaction with an activated nickel(0) reagent.

Green halogenation of aromatic heterocycles using ammonium halide and hydrogen peroxide in acetic acid solvent

The green generation of X+ (X = Br, I) using hydrogen peroxide in aqueous acetic acid allows access to aromatic heterocyclic halides in yields and purities comparable to syntheses employing N-bromosuccinimide. In activated and unsubstituted thiophene rings, regioselectivity is quantitative for positions α to the sulfur; pyrroles also give quantitative reactions, at least initially. Deactivated rings, including furans and thiazoles, as well as thiophenes with strongly electron-withdrawing groups showed little to no reactivity under the conditions investigated. The reaction shows remarkable functional group tolerance (to alcohol, nitro, alkyl, halo, and carbonyl groups), as shown through reaction with substituted phenols. In all bromination reactions, reaction yields and regiochemistry were very similar to reactions involving N-bromosuccinimide in tetrahydrofuran solvent.

A novel method for the bromination of thiophenes

A novel, fast and convenient method for the bromination of thiophenes and oligothiophenes with N-bromosuccinimide (NBS) using ultrasonic irradiation is elaborated. The yield of bromothiophenes strongly depends on the initial thiophene structure and nature of the solvent.