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

Uses

5-Bromo-2,2′-bithiophene may be used in the synthesis of trimethyl-[2,2′;5′,2″;5″,2″]quaterthiophen-5-yl-silane (4TTMS) and 5-hexylsulfanyl-2,2′:5′,2′′-terthiophene.

General Description

5-Bromo-2,2′-bithiophene is a bromothiophene derivative. Its reaction with various aryl iodides bearing an electron-donating or electron-withdrawing substituent has been described. It can be synthesized from 2,2′-bithiophene.

Upstream product

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

Downstream Products

• 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 
• 492-97-7 2,2'-Bithiophene 
• 371149-37-0 5-piperidino-2,2'-bithiophene 
• 316127-65-8 8-([2,2'-bithiophen]-5-ylethynyl)-3,3-diphenyl-3H-naphtho[2,1-b]pyran 
• 327630-34-2 5-Perfluorohexyl-2,2'-dithiophene 
• 151271-42-0 2-hexyl-5-(5-(thiophen-2-yl)thiophen-2-yl)thiophene 

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.