16939-04-1

Basic information

• Product Name: (4-THIEN-2-YLPHENYL)METHANOL
• Synonyms: 4-(Thien-2-yl)benzyl alcohol;2-p-Tolylthiophene;2-p-Tolyl-thiophene(7CI,8CI);(4-(Thiophen-2-yl)phenyl)Methanol;4-(Thien-2-yl)toluene, 1-Methyl-4-(thien-2-yl)benzene
• CAS NO: 16939-04-1
• Molecular Formula: C₁₁H₁₀S
• Molecular Weight: 190.2615
• Mol File: 16939-04-1.mol

Chemical Properties

• Boiling Point: 338.5 °C at 760 mmHg
• Flash Point: 158.5 °C
• Appearance: /
• Density: 1.204 g/cm³
• Vapor Pressure: 3.8E-05mmHg at 25°C
• Refractive Index: 1.622
• Storage Temp.: Room temperature.
• CAS DataBase Reference: (4-THIEN-2-YLPHENYL)METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (4-THIEN-2-YLPHENYL)METHANOL(16939-04-1)
• EPA Substance Registry System: (4-THIEN-2-YLPHENYL)METHANOL(16939-04-1)

Safety Data

• Hazard Codes: Harmful:
• Hazardous Substances Data: 16939-04-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(4-THIEN-2-YLPHENYL)METHANOL serves as a key building block in the creation of various pharmaceuticals. Its unique structure allows it to be a fundamental component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Organic Synthesis:
In the realm of organic synthesis, (4-THIEN-2-YLPHENYL)METHANOL is utilized for the preparation of different types of compounds, such as ketones, esters, and amines. Its reactivity and chemical properties make it an indispensable tool for organic chemists.
Used in Antimicrobial Applications:
(4-THIEN-2-YLPHENYL)METHANOL has been investigated for its potential as an antimicrobial agent. Its ability to combat microorganisms makes it a promising candidate for use in various industries, including healthcare and pharmaceuticals, to develop new treatments and preventive measures against infections.
Used in Anti-Inflammatory Applications:
(4-THIEN-2-YLPHENYL)METHANOL has also demonstrated potential as an anti-inflammatory agent. This property opens up opportunities for its use in the development of medications aimed at reducing inflammation and managing inflammatory conditions.
Overall, (4-THIEN-2-YLPHENYL)METHANOL's unique structure and potential applications make it a valuable asset in the fields of organic chemistry and medicinal research, with broad implications for the development of new pharmaceuticals and other organic compounds.

InChI:InChI=1/C11H10OS/c12-8-9-3-5-10(6-4-9)11-2-1-7-13-11/h1-7,12H,8H2

Upstream product

• 188290-36-0 thiophene 
• 51274-57-8 1-(4-Methylphenyl)-3,3-(1,5-pentanediyl)triazene 
• 96-43-5 2-thienyl chloride 
• 108-88-3 toluene 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 3027-21-2 dimethoxy(methyl)phenylsilane 
• 624-31-7 4-tolyl iodide 
• 17881-88-8 methoxydimethylphenylsilane 
• 696-61-7 4-tolylmagnesium chloride 
• 1003-09-4 2-bromothiophene 
• 5720-05-8 4-methylphenylboronic acid 
• 106-49-0 p-toluidine 
• 3437-95-4 2-Iodothiophene 
• 6729-64-2 tri(p-tolyl)bismuth dichloride 

Downstream Products

• 101093-85-0 4-oxo-4-[5-(p-tolyl)-2-thienyl]butanoic acid 
• 859055-63-3 1-(5-p-tolyl-[2]thienyl)-propan-1-one 
• 855631-70-8 phenyl[5-(4-methylphenyl)thiophene-2-yl]methanone 
• 860367-85-7 (4-methoxy-phenyl)-(5-p-tolyl-[2]thienyl)-ketone 
• 51335-91-2 1-[5-(4-methylphenyl)thiophene-2-yl]ethanone 
• 854468-05-6 1-(5-p-tolyl-[2]thienyl)-butan-1-one 
• 845753-53-9 2-bromo-5-(4-methylphenyl)thiophene 
• 83495-22-1 5,5'-Di-p-tolyl-[2,3']bithiophenyl 
• 38401-68-2 5-(4-methylphenyl)thiophene-2-carbaldehyde 
• 61100-11-6 ethyl 5-(p-tolyl) thiophene-2-carboxylate 
• 40808-21-7 5-(4-methylphenyl)thiophene-2-carboxylic acid 
• 184041-10-9 5-(4'-methylphenyl)-thiophene-2-sulfonyl chloride 

Relevant articles and documents

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TiPd alloys have been found to be novel heterogeneous palladium catalysts for organic cross-coupling reactions. Catalyst preactivation is not necessary, resulting in facile recovery and reuse of the catalysts. Palladium is not leached into the reaction solution and the catalysts can be recycled several times without losing their catalytic activity.

[{Pd(μ-OH)Cl(IPr)}2]—A Highly Efficient Precatalyst for Suzuki–Miyaura Coupling also Able To Act under Base-Free Conditions

[{Pd(μ-OH)Cl(IPr)}2] [IPr=N,N-bis(2,6-diisopropylphenyl)imidazol-2-ylidene] was found to be a highly efficient precatalyst for Suzuki–Miyaura coupling that is able to act under base-free conditions.

4-Amino-1,2,4-triazoles-3-thiones and 1,3,4-oxadiazoles-2-thiones·palladium(II) recoverable complexes as catalysts in the sustainable Suzuki-Miyaura cross-coupling reaction

The Suzuki-Miyaura cross-coupling reaction using 4-amino-1,2,4-triazoles and 1,3,4-oxadiazoles-2-thiones·palladium (II) is studied. The reaction is optimized and the most appropriate catalytic complex is tested with several aryl halides, boronic acids in an environmentally benign solvent system (H2O/EtOH). The recovery of the catalytic species is also surveyed because of the nature of the employed solvent. A domino process is efficiently carried out following the standard conditions. Several surface parameters of the ligands are analyzed and the resulting values are extrapolated to the insoluble palladium catalyst.

Hypervalent iodine in synthesis XXXIII: Palladium-catalyzed cross- coupling reaction of potassium aryltrifluoroborates with diaryliodonium salts and hydroxy(tosyloxy)iodobenzene

Potassium aryltrifluoroborates react smoothly with diaryliodonium salts and hydroxy(tosyloxy)iodobenzene, PhI(OH)OTs, under mild conditions in the presence of a palladium catalyst and without added base to afford biaryls in excellent yields.

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Direct C-H arylation of unactivated heteroaromatics with aryl halides catalyzed by cobalt porphyrin is reported. The reaction is proposed to go through a homolytic aromatic substitution reaction. The aryl radical is electrophilic and a SOMO-HOMO interaction is predominant in the aryl radical addition process.

Synthesis and characterization of palladium nanoparticles immobilized on graphene oxide functionalized with triethylenetetramine or 2,6-diaminopyridine and application for the Suzuki cross-coupling reaction

Graphene oxide (GO) was functionalized with two organic ligands, triethylenetetramine (TETA) or 2,6-diaminopyridine (DAP), followed by palladium nanoparticles (Pd NPs) for the synthesis of Pd NPs/GO-TETA and Pd NPs/GO-DAP nanocomposites, respectively. The two heterogeneous nanocomposites were fully characterized and their efficiency was investigated for C[sbnd]C bond formation for the synthesis of biaryl compounds via the Suzuki cross-coupling reaction of aryl halides with arylboronic acid derivatives. The obtained results indicated that the Pd NPs/GO-TETA nanocomposite was more effective in the Suzuki coupling reaction as compared to Pd NPs/GO-DAP. Thus, the Suzuki cross-coupling reaction of different aryl halides with arylboronic acid derivatives using Pd NPs/GO-TETA nanocomposite catalyst in the presence of Na2CO3 as base in DMF/H2O (1/1) as solvent at 90 °C was carried out to afford the desired biaryl compounds in high to excellent yields (81–100%) and short reaction times (10–90 min). Additionally, Pd NPs/GO-TETA nanocomposite can be recovered and reused for 8 consecutive runs without any apparent loss of its catalytic activity, proving its high stability and potential use in organic transformations.

Suzuki-Miyaura Cross-Coupling Reaction with Potassium Aryltrifluoroborate in Pure Water Using Recyclable Nanoparticle Catalyst

This paper describes the Suzuki Miyaura cross-coupling reaction of aryl bromides with potassium aryltrifluoroborates in water catalyzed by linear polystyrene-stabilized PdO nanoparticles (PSPdONPs). The reaction of aryl bromides having electron-withdrawing groups or electron-donating groups took place smoothly to give the corresponding coupling product in high yields. The catalyst recycles five times without significant loss of catalytic activity although a little bit increase in size of PdNPs was observed after the reaction.

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

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A photocatalytic ensemble HP-T?Au-Fe3O4: Synergistic and balanced operation in Kumada and Heck coupling reactions

A supramolecular catalytic ensemble HP-T?Au-Fe3O4 supported by highly branched assemblies of hexaphenylbenzene (HPB) derivatives has been developed. The as-prepared HP-T?Au-Fe3O4 nanohybrid material serves as an efficient catalytic system to prepare biaryl derivatives through the Kumada cross-coupling reaction using aryl chlorides as one of the coupling partners under mild reaction conditions (visible light irradiation, aqueous media, aerial conditions, short reaction time). Through the cooperative effect of Au NPs and Fe3O4 NPs, dual activation of aryl chlorides for the generation of aryl radical intermediates is achieved. On the other hand, oligomeric assemblies contributed significantly to the enhancement of the reaction rate and yield of the product by facilitating the reductive elimination step. Different mechanistic studies confirm the involvement of Au NPs, Fe3O4 NPs and oligomeric assemblies in the synergistic and balanced operation of HP-T?Au-Fe3O4 nanohybrid materials in the efficient completion of the catalytic cycle of the Kumada coupling reaction. Being magnetic, the catalytic ensemble could be recycled for up to five catalytic cycles. The as-prepared supramolecular photocatalytic ensemble also works efficiently in Heck coupling reactions involving aryl chlorides and aryl iodides as the coupling partner.