1445-78-9

Basic information

• Product Name: 2,5-DIPHENYLTHIOPHENE
• Synonyms: 2,5-DIPHENYLTHIOPHENE;THIOPHENE, 2,5-DIPHENYL-
• CAS NO: 1445-78-9
• Molecular Formula: C₁₆H₁₂S
• Molecular Weight: 236.33
• Product Categories: Sulphur Derivatives
• Mol File: 1445-78-9.mol
• Article Data: 94

Chemical Properties

• Melting Point: 153 °C
• Boiling Point: 366.6°Cat760mmHg
• Flash Point: 130.9°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 3.06E-05mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: 2-8°C
• Solubility: soluble in Toluene
• CAS DataBase Reference: 2,5-DIPHENYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-DIPHENYLTHIOPHENE(1445-78-9)
• EPA Substance Registry System: 2,5-DIPHENYLTHIOPHENE(1445-78-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1445-78-9(Hazardous Substances Data)

Usage

Description

2,5-Diphenylthiophene is an organic sulfur compound, characterized by the presence of a thiophene ring with two phenyl groups attached at the 2nd and 5th positions. It is derived from ethylbenzene and sulfur, and is known for its unique chemical properties and potential applications in various industries.

Uses

Used in Chemical Synthesis:
2,5-Diphenylthiophene is used as a key intermediate in the synthesis of various organic compounds, particularly those with sulfur-containing structures. Its unique molecular configuration allows for the creation of a wide range of products, including pharmaceuticals, dyes, and specialty chemicals.
Used in Electronics Industry:
In the electronics industry, 2,5-diphenylthiophene is utilized as a material for the development of organic semiconductors and optoelectronic devices. Its electronic properties, such as its ability to conduct electricity and its light-emitting characteristics, make it a promising candidate for applications in organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs).
Used in Polymer Industry:
2,5-Diphenylthiophene is also used as a monomer in the polymer industry for the production of novel polymers with specific properties. These polymers can be tailored for various applications, such as in the development of high-performance materials for coatings, adhesives, and composites.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,5-diphenylthiophene serves as a building block for the synthesis of therapeutic agents with potential biological activities. Its unique chemical structure allows for the design of new drugs targeting various diseases and medical conditions.
Used in Environmental Applications:
2,5-Diphenylthiophene can be employed in environmental applications, such as in the development of materials for pollution control and remediation. Its sulfur-containing structure may offer advantages in the adsorption and removal of heavy metals and other contaminants from the environment.

Synthesis Reference(s)

The Journal of Organic Chemistry, 57, p. 1722, 1992 DOI: 10.1021/jo00032a024Tetrahedron Letters, 20, p. 243, 1979

InChI:InChI=1/C16H12S/c1-3-7-13(8-4-1)15-11-12-16(17-15)14-9-5-2-6-10-14/h1-12H

Upstream product

• 100-42-5 styrene 
• 512-22-1 2,4,6-trimethyl-2,4,6-triphenyl-[1,3,5]trithiane 
• 621-82-9 Cinnamic acid 
• 98-86-2 acetophenone 
• 495-71-6 phenacylacetophenone 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 42963-87-1 2,5-diphenyl-[1,4]dithiin-1,1-dioxide 
• 536-74-3 phenylacetylene 
• 53268-89-6 1-hydro-1-methyldibenzosilole 
• 140-10-3 (E)-3-phenylacrylic acid 
• 625-88-7 2,5-diiodothiophene 
• 24388-23-6 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole 
• 825-55-8 2-phenylthiophene 
• 108-86-1 bromobenzene 

Downstream Products

• 51092-02-5 2,5-bis(phenyl)-thiophene-1,1-dioxide 
• 23852-94-0 3,4-dichloro-2,5-diphenyl-thiophene 
• 874511-95-2 3,4-dibromo-2,5-diphenylthiophene 
• 959-27-3 (Z)-1,4-diphenylbut-2-ene-1,4-dione 
• 65-85-0 benzoic acid 
• 188483-20-7 5-benzoyl-3-phenylisothiazole 
• 7688-03-1 1,1-dimethyl-2,5-diphenylsilole 
• 437606-44-5 2,5-diphenyl-3-thiophenecarbonitrile 
• 494840-44-7 5,7-diphenyl-1,4-dihydro-1H-3λ⁴-thieno[3,4-d][2,3]-oxathiin-3-oxide 

Relevant articles and documents

A Rational Design of Highly Controlled Suzuki-Miyaura Catalyst-Transfer Polycondensation for Precision Synthesis of Polythiophenes and Their Block Copolymers: Marriage of Palladacycle Precatalysts with MIDA-Boronates

Herein, we report a highly efficient Suzuki-Miyaura catalyst-transfer polycondensation (SCTP) of 3-alkylthiophenes using bench-stable but highly active Buchwald dialkylbiarylphospine Pd G3 precatalysts and N-methylimidodiacetic (MIDA)-boronate monomers. Initially, the feasibility of the catalyst-transfer process was examined by screening various dialkylbiarylphospine-Pd(0) species. After optimizing a small molecule model reaction, we identified both RuPhos and SPhos Pd G3 precatalysts as excellent catalyst systems for this purpose. On the basis of these model studies, SCTP was tested using either RuPhos or SPhos Pd G3 precatalyst, and 5-bromo-4-n-hexylthien-2-yl-pinacol-boronate. Poly(3-hexylthiophene) (P3HT) was produced with controlled molecular weight and narrow dispersity for a low degree of polymerization (DP) only, while attempts to synthesize P3HT having a higher DP with good control were unsuccessful. To improve the control, slowly hydrolyzed 5-bromo-4-n-hexylthien-2-yl-MIDA-boronate was introduced as a new monomer. As a result, P3HT and P3EHT (up to 17.6 kg/mol) were prepared with excellent control, narrow dispersity, and excellent yield (>90%). Detailed mechanistic investigation using 31P NMR and MALDI-TOF spectroscopy revealed that both fast initiation using Buchwald precatalysts and the suppression of protodeboronation due to the protected MIDA-boronate were crucial to achieve successful living polymerization of P3HT. In addition, a block copolymer of P3HT-b-P3EHT was prepared via SCTP by sequential addition of each MIDA-boronate monomer. Furthermore, the same block copolymer was synthesized by one-shot copolymerization for the first time by using fast propagating pinacol-boronate and slow propagating MIDA-boronate.

Thiophene 1-Oxides. V [1], [2], [3], [4]. Comparison of the Crystal Structures and Thiophene Ring Aromaticity of 2,5-Diphenylthiophene, its Sulfoxide and Sulfone

The detailed preparation of 2,5-diphenylthiophene 1-oxide (2) is reported as well as the comparative study of the crystal structures of 2,5-diphenylthiophene, 1, its sulfoxide 2 and sulfone 3 obtained by X-ray diffraction. This work represents the first e

Synthesis of heterocyclic compounds with adamantane-like cage structures consisting of phosphorus, sulfur, and carbon

The synthesis of novel adamantane-like cage compounds consisting of phosphorus, sulfur, and carbon atoms was developed. We examined the reaction of a variety of acetophenone derivatives with P4S10 in refluxing benzene. A novel noradamantane-like cage compound was also synthesized, when the reaction of 2’-methoxyacetophenone with P4S10 was performed in refluxing toluene. In addition, by using the adamantane-like cage compound, 4,4’-dimethoxybenzophenone and N,N-dimethylbenzamide were successfully transformed into the corresponding thioketone (98%) and benzothioamide (89%), respectively.

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Diels-alder reaction and double phenylation in reaction of thiophenes with diphenyliodonium triflate

The reaction of 2,5-dimethylthiophene with diphenyliodonium triflate in the presence of N-phenylmaleimide and a catalytic amount of Cu(OAc)2 gave 1:1 and 1:2 cycloadducts with N-phenylmaleimide. The similar reactions of 2,5-bis(trimethylsilyl)thiophene, 3-phenylthiophene, and thiophene afforded 2,5-diphenylthiophene, 2,3,5-triphenylthiophene, and 2,5-diphenylthiophene, respectively. The cycloadducts and 2,5-diphenylated thiophenes are considered to be formed via S-phenylation of thiophenes affording 1-phenylthiophenium triflates.

Silver-Catalyzed Regio- and Stereoselective Thiocyanation of Haloalkynes: Access to (Z)-Vinyl Thiocyanates

A regio- and stereoselective method for the preparation of (Z)-vinyl thiocyanate derivatives by silver-catalyzed thiocyanation of haloalkynes is reported. This method features practical, free of ligand, broad substrate scope, excellent stereoselectivity and gram-scale synthesis. Significantly, the halogen atom of haloalkynes is retained, which allows the synthesis of 2,5-diphenylthiophene, thiazol-2-amine and trifluoromethyl sulfides derivatives via simple transformation. (Figure presented.).

Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles

An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles.

Photocatalytic Activation of Elemental Sulfur Enables a Chemoselective Three-Component Thioesterification

A mild and chemoselective three-component thioesterification using olefins, α-ketoacids, and elemental sulfur has been developed. The photocatalytic activation of elemental sulfur, a cheap and abundant sulfur source, enables the rapid installation of a su