4805-22-5

Basic information

• Product Name: 5,5'-Dibromo-2,2'-bithiophene
• Synonyms: 5,5'-DIBROMO-2,2'-BITHIOPHENE;SPECS AC-776/41252583;5,5'-dibromo-2,2'-dithiophene;5,5''-DIBROMO-2,2''-BITHIOPHENE: 99.8%;2,2'-Bi(5-bromothiophene);5,5'-Dibromo-2,2'-bithiophene,99%;2-broMo-5-(5-broMothiophen-2-yl)thiophene;2,5'-DibroMobithiophene
• CAS NO: 4805-22-5
• Molecular Formula: C₈H₄Br₂S₂
• Molecular Weight: 324.06
• EINECS: 1312995-182-4
• Product Categories: Thiophenes;Functional Materials;Reagents for Conducting Polymer Research;Thiophene Derivatives (for Conduting Polymer Research);Thiophen;Heterocycles;Halogenated Heterocycles;Heterocyclic Building Blocks;Organic Electronics and Photonics;Synthetic Tools and Reagents;Thiophene Monomers and Building BlocksHeterocyclic Building Blocks;ThiophenesBuilding Blocks;Thiophene Series
• Mol File: 4805-22-5.mol

Chemical Properties

• Melting Point: 144-146 °C(lit.)
• Boiling Point: 318.6 °C at 760 mmHg
• Flash Point: 146.5 °C
• Appearance: white to light yellow shiny flakes
• Density: 1.951 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 5,5'-Dibromo-2,2'-bithiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5'-Dibromo-2,2'-bithiophene(4805-22-5)
• EPA Substance Registry System: 5,5'-Dibromo-2,2'-bithiophene(4805-22-5)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4805-22-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5,5'-Dibromo-2,2'-bithiophene is used as an active pharmaceutical ingredient due to its potential applications in the development of new drugs. Its unique chemical structure allows it to be a valuable building block for creating novel therapeutic agents.
Used in OLED Industry:
In the field of organic light-emitting diode (OLED) technology, 5,5'-Dibromo-2,2'-bithiophene serves as an intermediate material. Its electronic properties make it suitable for use in the design and synthesis of advanced OLED materials, which are crucial for improving the performance and efficiency of OLED devices.
Used in Polymer Synthesis:
5,5'-Dibromo-2,2'-bithiophene is also utilized as a termination reagent in polymerization processes. Its chemical properties enable it to effectively control the molecular weight and dispersity of the resulting polymers, which is essential for achieving desired material properties and applications in various industries.

Upstream product

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• 29504-81-2 5-iodo-2-bromothiophene 
• 1003-09-4 2-bromothiophene 
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Downstream Products

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• 132814-91-6 3,3'-dihexyl-2,2':5',2:5,2'-quarterthiophene 
• 369599-42-8 5,5'-bis-(7-hexyl-9H-fluoren-2-yl)-[2,2']bithiophene 
• 212702-86-8 trans-PdBr(C₈H₄BrS₂-C)(PPh₃)2 
• 1067186-03-1 C₅₄H₄₀N₆O₄S₂ 
• 1067186-02-0 C₅₀H₃₂N₆S₂ 
• 1113063-40-3 5,5'-bis(4,4-di-p-tolyl-4H-indeno[1,2-b]thien-2-yl)-2,2'-bithiophene 
• 860435-89-8 5,5'-di(4-ethynyl-N,N-dimethylaniline)-2,2'-bithiophene 
• 51285-60-0 4,4’-dibromo-2,2’-bithiophene 
• 16303-58-5 5,5'-dimethyl-2,2'-dithiophene 
• 146796-00-1 5'-bromo-5-methyl-2,2'-bithiophene 
• 1059502-56-5 5-bromo-5-((hydroxy)phenylmethyl)-2,2-bithiophene 

Relevant articles and documents

Emission enhancement of a carbazole-based fluorophore on a quantum dot surface

A novel carbazole-based fluorophore 5-(carbazol-9-yl)-5′-mercapto-2, 2′-bithiophene (CBTSH) was synthesized. CBTSH exhibited emission enhancement when attached to the surface of CdSe quantum dots (QDs). The emission quantum yield of CBTSH attached to CdSe is almost 5 times larger than that of CBTSH alone. The emission enhancement of CBTSH on the CdSe surface is due to the restriction on the rotational and vibrational motions of the carbazolylbithienyl unit as a result of QD aggregation.

Synthesis and Characterization of α,α'-Bis(aminomethyl)oligothiophenes and Their Related Compounds

We have synthesized and characterized a series of novel compounds of α,α'-bis(aminomethyl)oligothiophenes and their related compounds whose degree of polymerization spans two (dimer) to five (pentamer). The compounds presented in our studies are α,α'-bis[(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopenthyl)methyl] oligothiophene, α,α'-bis(aminomethyl)oligothiophene dihydrochloride and α,α'- bis(aminomethyl)oligothiophene. These compounds exhibit desired chemical activity while maintaining controllable electronic properties. The synthetic processes of the oligothiophenes are as follows: 2-aminomethylthiophene is first 'protected' and the thiophene rings are coupled using standard Grignard methods. The protected groups are removed at the final stage of the reaction. The compounds show unique properties; for example α,α'-bis(aminomethyl)oligothiophene dihydrochloride is soluble in water. The results of electronic spectra and duration are also presented.

A star-shaped oligothiophene with triphenylamine as core and octyl cyanoacetate as end groups for solution-processed organic solar cells

A new star-shaped D-π-A molecule with triphenylamine (TPA) as core and donor unit, octyl cyanoacetate (CA) as end group and acceptor unit, and 2,2′-bithiophene vinylene (bTV) as π bridge, S(TPA-bTV-CA) was designed and synthesized for the application as donor materials in solution-processed bulk-heterojunction organic solar cells (OSCs). The compound is soluble in common organic solvents. The thermal, optical and electrochemical properties of the star molecule were studied. The OSC devices were fabricated by spin-coating the blend solution of the molecule as donor and PC70BM as acceptor (1:3, w/w). The OSC device based on S(TPA-bTV-CA)/PC70BM demonstrated a high open circuit voltage of 0.91 V, a short circuit current density of 4.64 mA/cm2, a fill factor (FF) of 50%, corresponding to a power conversion efficiency of 2.1%, under the illumination of AM 1.5, 100 mW/cm 2.

Improved synthesis of a quaterthiophene-triazine-diamine derivative, a promising molecule to study pathogenic prion proteins

The 6,6′-([2,2′:5′,2″:5″,2-quaterthiophene]-5,5-diyl)bis(1,3,5-triazine-2,4-diamine) (MR100), has been previously investigated in our research group through its biological activities toward pathogenic prion proteins (PrPSc). This compound presents a high affinity to protein strains and interacts selectively with at least one β-sheet rich isoform of prion protein. Herein we present the improved total synthesis of MR100, through a palladium-catalyzed direct double arylation using the concerted metalation deprotonation mechanism (CMD).

Synthesis of 2-Bromo-2′-phenyl-5,5′-thiophene: Suzuki reaction versus Negishi reaction

2-Bromo-2′-phenyl-5,5′-thiophene was synthesized by cross-coupling reaction of phenylboric acid and 2,2′-dibromo-5,5′-bithiophene with a Suzuki reaction; we found the Suzuki reaction to give a higher yield when compared to the Negishi reaction.

Synthesis and structure of tetrathiophene with a chiral 1,1′-binaphthyl kink

A chiral oligothiophene, possessing in-chain chirality, was prepared and its racemate was characterized by single crystal X-ray crystallography; the in-chain chiral 1,1′-binaphthyl moiety interrupts the π-conjugation and affects the solid state properties

Aryl halide and synthesis method and application thereof

The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.

Visible-light-promoted oxidative halogenation of (hetero)arenes

Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.

Pd-Catalyzed Aerobic Oxidative Coupling of Thiophenes: Synergistic Benefits of Phenanthroline Dione and a Cu Cocatalyst

Substituted bithiophenes are prominent fragments in functional organic materials, and they are ideally prepared via direct oxidative C-H/C-H coupling. Here, we report a novel PdII catalyst system, employing 1,10-phenanthroline-5,6-dione (phd) as the ancillary ligand, that enables aerobic oxidative homocoupling of 2-bromothiophenes and other related heterocycles. These observations represent the first use of phd to support Pd-catalyzed aerobic oxidation. The reaction also benefits from a Cu(OAc)2 cocatalyst, and mechanistic studies show that Cu promotes C-C coupling, implicating a role for CuII different from its conventional contribution to reoxidation of the Pd catalyst.

Sterically controlled C-H/C-H homocoupling of arenes: Via C-H borylation

A mild one-pot protocol for the synthesis of symmetrical biaryls by sequential Ir-catalyzed C-H borylation and Cu-catalyzed homocoupling of arenes is described. The regiochemistry of the biaryl formed is sterically controlled as dictated by the C-H borylation step. The methodology is also successfully extended to heteroarenes. Some of the products obtained by this approach are impossible to obtain via the Ullmann or the Suzuki coupling protocols. Finally, we have shown a one-pot sequence describing C-H borylation/Cu-catalyzed homocoupling/Pd-catalyzed Suzuki coupling to obtain π-extended arene frameworks.