13781-37-8

Basic information

• Product Name: 2-iodo-5-phenylthiophene
• Synonyms: 2-iodo-5-phenylthiophene;Thiophene, 2-iodo-5-phenyl- (Related Reference)
• CAS NO: 13781-37-8
• Molecular Formula: C₁₀H₇IS
• Molecular Weight: 286.13205
• Mol File: 13781-37-8.mol

Chemical Properties

• Melting Point: 82.0 to 86.0 °C
• Boiling Point: 329.1±30.0 °C(Predicted)
• Appearance: /
• Density: 1.720±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• CAS DataBase Reference: 2-iodo-5-phenylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-iodo-5-phenylthiophene(13781-37-8)
• EPA Substance Registry System: 2-iodo-5-phenylthiophene(13781-37-8)

Safety Data

• Hazardous Substances Data: 13781-37-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
2-iodo-5-phenylthiophene is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its unique structure and reactivity. Its presence in the molecular framework allows for the development of new compounds with potential therapeutic and pesticidal properties.
Used in Organic Synthesis:
As a building block in organic synthesis, 2-iodo-5-phenylthiophene is utilized for the preparation of a wide range of organic compounds. Its reactivity and structural features enable the formation of diverse molecular architectures, contributing to the discovery of new chemical entities with potential applications in various fields.
Used in Materials Science:
2-iodo-5-phenylthiophene is employed in materials science for the development of novel materials with specific properties. Its incorporation into polymers, coatings, and other materials can enhance their performance, leading to improved applications in electronics, sensors, and other industries.
Used as a Ligand in Transition Metal-Catalyzed Cross-Coupling Reactions:
In the field of organic chemistry, 2-iodo-5-phenylthiophene serves as a promising ligand for transition metal-catalyzed cross-coupling reactions. Its ability to form stable complexes with transition metals facilitates the formation of carbon-carbon and carbon-heteroatom bonds, enabling the synthesis of complex molecular structures with high selectivity and efficiency. This application expands the scope of organic synthesis and contributes to the development of new methodologies and catalyst systems.

Upstream product

• 825-55-8 2-phenylthiophene 
• 7553-56-2 iodine 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1665-31-2 5-phenyl-[2,2'-bithienyl] 
• 492-97-7 2,2'-Bithiophene 
• 83495-30-1 5,5′-diphenyl-2,2′-bithiophene 
• 1665-32-3 5,5-diphenyl-2,2':5',2-terthiophene 
• 1204-82-6 2-Phenyl-5-(1'-propynyl)-thiophene 
• 256342-39-9 1,4-bis(5-phenylthiophene-2-yl)benzene 
• 641609-90-7 C₃₅H₂₂F₆S₄ 
• 641609-91-8 C₃₉H₃₀F₆S₄ 
• 1665-35-6 5-ethynyl-2-phenylthiophene 
• 94742-70-8 2-phenyl-5-(3-buten-1-ynyl)thiophen 
• 96924-60-6 (E)-3-chloro-2-methyl-3-(5-phenyl-2-thienyl)acrolein 
• 96924-61-7 (Z)-3-chloro-2-methyl-(5-phenyl-2-thienyl)acrolein 
• 62404-17-5 N-(5-phenyl-2-thenoyl)piperidine 
• 17361-89-6 5-phenyl-2-thiophene carbonyl chloride 

Relevant articles and documents

Synthesis of thiophene/phenylene co-oligomers. I. Phenyl-capped oligothiophenes

We report the synthesis of phenyl-capped oligothiophenes via improved synthetic schemes. These schemes are based on the Grignard coupling reaction and enable us to obtain the target compounds at high yields. The resulting materials have been fully charact

Regiospecific palladium-catalyzed cross-coupling reactions using the operational equivalent of 1,3-dilithiopropyne

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Light-controlled reversible modulation of frontier molecular orbital energy levels in trifluoromethylated diarylethenes

Among bistable photochromic molecules, diarylethenes (DAEs) possess the distinct feature that upon photoisomerization they undergo a large modulation of their pelectronic system, accompanied by a marked shift of the HOMO/LUMO energies and hence oxidation/

The preparations and some properties of mixed aryl-thienyl oligomers and polymers

The syntheses by transition metal coupling reactions of a large number of oligomers constructed from benzene and thiophene rings are described. The first use of arylcadmium chlorides for such coupling reactions is reported. The routes chosen allow for rational variation in the modes of linkage, the substitution and the proportions of the two units. The benzene and thiophene rings are always joined in a known order and may bear a wide variety of regularly spaced functional groups. Additionally the shape of the oligomers may be varied at will. In all cases p-type doping with iodine or ferric chloride leads to large enhancements in conductivity.

PALLADIUM-CATALYZED SYNTHESES OF NATURALLY-OCCURRING ACETYLENIC THIOPHENS AND RELATED COMPOUNDS

5-(3-buten-1-ynyl)-2,2'-bithienyl (1a), a natural product first isolated from Tagetes roots which shows nematicidal and photo-induced fungicidal activity, and 2-phenyl-5-(3-buten-1-ynyl) thiophen (1b) have been synthesized using two different methods.The first one (Method A) involves the palladium-catalyzed cross-coupling of vinyl bromide with the Grignard reagents derived from 5-ethynyl-2,2'-bithienyl (6a) and 2-ethynyl-5-phenylthiophen (6b).The second method (Method B) utilizes the coupling reaction of vinyl bromide with 6a and 6b, respectively, in the presence of a catalytic amount of (PPh3)4Pd and CuI.Such reaction, which was carried out under phase-transfer conditions employing BnEt3N(+)Cl(-) as phase transfer agent and 2.5N aq NaOH as base, has been also employed to prepare a large number of heterocyclic acetylene derivatives including some naturally-occuring compounds.The experimental conditions of Method B allow also the direct production of heterocyclic acetylene derivatives (1) starting from 1-alkynyltrimethylsilanes (5) and organic halides (2).