625-88-7

Basic information

• Product Name: 2,5-DIIODOTHIOPHENE
• Synonyms: 2,5-DIIODOTHIOPHENE;2,5-Diiodothiophene,99%;2,5-DIIODOTHIOPHENE,98%;2,5-Diiodothiophene 98%
• CAS NO: 625-88-7
• Molecular Formula: C₄H₂I₂S
• Molecular Weight: 335.93
• EINECS: 210-915-9
• Product Categories: Heterocycles series;Thiophene&Benzothiophene;Thiophens;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks
• Mol File: 625-88-7.mol

Chemical Properties

• Melting Point: 37-41 °C(lit.)
• Boiling Point: 139-140 °C(lit.)
• Flash Point: 205 °F
• Appearance: /solid
• Density: 2.6310 (estimate)
• Vapor Pressure: 0.00976mmHg at 25°C
• Refractive Index: 1.756
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 109915
• CAS DataBase Reference: 2,5-DIIODOTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIIODOTHIOPHENE(625-88-7)
• EPA Substance Registry System: 2,5-DIIODOTHIOPHENE(625-88-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 625-88-7(Hazardous Substances Data)

Usage

Uses

Used in Electronics Industry:
2,5-Diiodothiophene is used as a material for the preparation of oligothiophene films, which are essential components in the development of electronic devices and systems. The application reason is its ability to form thin films with desired electronic properties, contributing to the performance of the devices.
Used in Polymer Science:
2,5-Diiodothiophene is used as a monomer in the synthesis of oligothiophene and polythiophene micropatterns. The application reason is its chemical properties, which allow for the formation of well-defined and ordered micropatterns with potential applications in various fields, such as sensors, displays, and photovoltaics.
Used in Maskless Fabrication:
2,5-Diiodothiophene is used as a material for maskless fabrication of periodic patterns of a conjugated polymer. The application reason is its compatibility with maskless fabrication techniques, enabling the creation of complex and precise patterns without the need for a physical mask, thus reducing costs and increasing design flexibility.

InChI:InChI=1/C4H2I2S/c5-3-1-2-4(6)7-3/h1-2H

Upstream product

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Downstream Products

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• 1665-32-3 5,5-diphenyl-2,2':5',2-terthiophene 
• 527-72-0 2-thiophenylcarboxylic acid 
• 854477-35-3 2,5-bis-(2-carboxy-phenylsulfanyl)-thiophene 
• 30955-94-3 2-acetyl-5-iodothiophene 
• 19259-10-0 2,3,5-triiodothiophene 
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• 4282-31-9 Thiophene-2,5-dicarboxylic acid 
• 58386-20-2 2,5-bismethoxythiophene 
• 1081-34-1 2,2':5',2''-terthiophene 
• 75882-52-9 (2,5-thiophenediyl)bis(triphenylphosphonium iodide) 
• 79109-69-6 2,5-bis-(trimethylsilyl)ethynylthiophene 
• 492-97-7 2,2'-Bithiophene 

Relevant articles and documents

Solvent-Free and Liquid-Phase Iodination of Thiophene Derivatives with Potassium Dichloroiodate Monohydrate

Iodination of a series of benzene and thiophene derivatives by potassium dichloroiodate monohydrate was studied with and without a solvent. The liquid substrates tend to be more reactive in water while the solid substrates afford better yields in dichloromethane or under the solvent-free conditions. The 2-substituted thiophenes show good to excellent yields whereas the yield for 3-substituted and 3,4- or 2,4-disubstituted thiophenes and benzene derivatives are significantly lower. The mechanochemical reaction of 5-carbaldehyde-2,2′-bithiophene shows excellent yields, while 2,2′-bithiophene gives practical yields only in dichloromethane. In the case of thiophene and N -acetyl- p -toluidine, electrophilic iodination is accompanied by a small extent of chlorination.

Clean and Efficient Iodination of Thiophene Derivatives

Iodination of thiophene derivatives is realized using a simple, fast, and efficient methodology. Iodination of thiophene and 2- or 3-substituted or 3,4-disubstituted thiophenes with N-iodosuccinimide (NIS) activated with 4-toluenesulfonic acid in ethanol gives pure iodinated products that require no further purification.

New approach to electrochemical iodination of arenes exemplified by the synthesis of 4-iodopyrazoles of different structures

The two-stage electrosynthesis of 4-iodosubstituted pyrazole derivatives was performed. At the first stage, KIO3 was obtained at the Ni anode under the undivided galvanostatic conditions of electrolysis of an aqueous alkaline solution of KI (or I2) at the Ni anode. At the second stage, pyrazole and its derivatives were iodinated in the heterophase (H2O-CHCl3 (CCl4)) medium by the KIO3-KI (or KIO3-I2) system in the presence of H2SO4. The yields of iodopyrazoles were 74-92%. The electrochemical iodination of anisole, 2-methylpyrazole, and thiophene was carried out to form 4-iodoanisole (88% yield), 4,5-diiodo-2-methylimidazole (54% yield), and a mixture of 2-iodothiophene (60% yield) and 2,5-diiodothiophene (4% yield).

Potassium-alkyl magnesiates: Synthesis, structures and Mg-H exchange applications of aromatic and heterocyclic substrates

Using structurally well-defined dipotassium-tetra(alkyl)magnesiates, a new straightforward methodology to promote regioselective Mg-H exchange reactions of a wide range of aromatic and heteroaromatic substrates is disclosed. Contacted ion pair intermediates are likely to be involved, with K being the key to facilitate the magnesiation processes. This journal is

Ultrasound-promoted rapid and efficient iodination of aromatic and heteroaromatic compounds in the presence of iodine and hydrogen peroxide in water

A rapid and efficient ultrasound-promoted protocol for iodination of aromatic and heteroaromatic compounds, using molecular iodine in the presence of aqueous hydrogen peroxide in water without any cosolvent, has produced versatile iodinated organic molecules with potential application in organic synthesis and medicine in short reaction times and good to excellent yields. Copyright

Efficient and eco-friendly synthesis of iodinated aromatic building blocks promoted by iodine and hydrogen peroxide in water: A mechanistic investigation by mass spectrometry

The reaction of aromatic and heteroaromatic compounds with molecular iodine in the presence of aqueous hydrogen peroxide using water without any co-solvent at 50 °C for 24 h produced versatile iodinated organic molecules with potential application in organic synthesis and medicine in very good yields. In addition, a mechanistic investigation for the iodination process was carried out by mass spectrometry.

METHOD OF PRODUCING IODIZING AGENT, AND METHOD OF PRODUCING AROMATIC IODINE COMPOUND

A method of the present invention, for producing an iodizing agent, includes the step of electrolyzing iodine molecules in a solution by using an acid as a supporting electrolyte. This realizes (i) a method of producing an iodine cation suitable for use as an iodizing agent that does not require a sophisticated separation operation after iodizing reaction is completed, and (ii) an electrolyte used in the method. Further, a method of the present invention, for producing an aromatic iodine compound, includes the step of causing an iodizing agent, and an aromatic compound whose nucleus has one or more substituent groups and two or more hydrogen atoms, to react with each other under the presence of a certain ether compound. This realizes such a method of producing an aromatic iodine compound that position selectivity in iodizing reaction of an aromatic compound is improved.

Deprotonative metalation of substituted benzenes and heteroaromatics using amino/alkyl mixed lithium-zinc combinations

Different homoleptic and heteroleptic lithium-zinc combinations were prepared, and structural elements obtained on the basis of NMR spectroscopic experiments and DFT calculations. In light of their ability to metalate anisole, pathways were proposed to justify the synergy observed for some mixtures. The best basic mixtures were obtained either by combining ZnCl 2·TMEDA (TMEDA = N,N,N',N'tetramethylethylenediamine) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 3 equiv) or by replacing one of the tmp in the precedent mixture with an alkyl group. The reactivity of the aromatic lithium zincates supposedly formed was next studied, and proved to be substrate-, base-, and electrophile-dependent. The aromatic lithium zincates were finally involved in palladium-catalyzed cross-coupling reactions with aromatic chlorides and bromides.

Co-thermolysis: A one-pot synthetic method for novel 2-substituted-5- (trifluoromethoxy)thiophenes

A new 'green' process to obtain trifluoromethoxylated compounds by a gas-phase method has been accomplished. Through it, new 2-substituted-5- (trifluoromethoxy)thiophenes have been obtained in moderate to good yields. Though the reaction occurs in the gas-phase and radicals are involved, an electron transfer mechanism is also postulated to explain the appearance of all detected products.

Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species

In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.