25664-48-6

Basic information

• Product Name: Benzofuran, 2-(4-methylphenyl)-
• CAS NO: 25664-48-6
• Molecular Formula: C15H12O
• Molecular Weight: 208.26
• Mol File: 25664-48-6.mol

Chemical Properties

• CAS DataBase Reference: Benzofuran, 2-(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzofuran, 2-(4-methylphenyl)-(25664-48-6)
• EPA Substance Registry System: Benzofuran, 2-(4-methylphenyl)-(25664-48-6)

Safety Data

• Hazardous Substances Data: 25664-48-6(Hazardous Substances Data)

Upstream product

• 60785-20-8 α,β-dichlorovinyl phenyl ether 
• 5720-05-8 4-methylphenylboronic acid 
• 98437-24-2 benzofuran-2-boronic acid 
• 624-31-7 4-tolyl iodide 
• 533-58-4 2-Iodophenol 
• 4186-14-5 1-(2-(trimethylsilyl)ethynyl)toluene 
• 190182-16-2 2-[2-(4-methylphenyl)vinyl]phenol 
• 2378-86-1 4-methylbenzyltriphenylphosphonium bromide 
• 459-44-9 4-methylbenzenediazonium tetrafluoroborate 
• 81787-62-4 o-((trimethylsilyl)ethynyl)phenol 
• 141-32-2 acrylic acid n-butyl ester 
• 259739-70-3 2-(2-phenylethynyl)phenol 
• 1257326-15-0 (E)-(1,2-dichlorovinyloxy)-2-deuteriobenzene 
• 1245947-03-8 (Z)-1-chloro-2-phenoxy-2-(4-methylphenyl)ethylene 

Downstream Products

• 50498-41-4 1-(2-p-tolyl-benzofuran-3-yl)-ethanone 
• 65203-77-2 4-[4-(4-benzofuran-2-yl-styryl)-phenyl]-2,5-diphenyl-2H-[1,2,3]triazole 
• 59151-67-6 4-[4-(4-benzofuran-2-yl-styryl)-phenyl]-2-phenyl-2H-[1,2,3]triazole 
• 71943-19-6 5-[4-(4-benzofuran-2-yl-styryl)-phenyl]-1,3-diphenyl-1H-pyrazole 
• 71943-11-8 3-[4-(4-benzofuran-2-yl-styryl)-phenyl]-1,5-diphenyl-1H-pyrazole 
• 71942-86-4 3-[4-(4-benzofuran-2-yl-styryl)-phenyl]-1-phenyl-1H-pyrazole 
• 71943-41-4 3-[4-(4-benzofuran-2-yl-styryl)-phenyl]-1-(4-chloro-phenyl)-1H-pyrazole 
• 53389-89-2 2-(4-(bromomethyl)phenyl)benzofuran 
• 1224447-56-6 2-(4-methylphenyl)-3-(4-fluorophenyl)benzofuran 
• 1224447-55-5 3-(3-methoxyphenyl)-2-(p-tolyl)benzofuran 
• 58491-52-4 2-(4-methylphenyl)benzofuran-3-carboxylic acid 

Relevant articles and documents

Synthesis, biological evaluation and molecular docking analysis of 2-phenyl-benzofuran-3-carboxamide derivatives as potential inhibitors of Staphylococcus aureus Sortase A

In Gram-positive bacteria, Sortase A (Srt A) is a critical cysteine transpeptidase that is responsible for recognizing and assembling surface virulence proteins through the recognition of a LPXTG (leucine, proline, X, threonine, and glycine, where X is an

Nickel/β-CD-catalyzed Suzuki–Miyaura cross-coupling of aryl boronic acids with aryl halides in water

In this study, a convenient nickel-catalyzed protocol has been introduced for the Suzuki–Miyaura coupling reaction. A simple mixture of Ni(II) and unfunctionalized β-cyclodextrin (β-CD) was used to cross-coupling of aryl halides with aryl boronic acids for the synthesis of biaryls in water. β-CD is a water-soluble seminatural cyclic oligosaccharide, environmentally friendly biomaterial, inexpensive, and commercially available ligand. This ligand with low solubility in usual organic solvents has been used for the synthesis of biaryls in good to excellent yields. The cross-coupling results in the presence of Ni(II)/β-CD catalytic system showed that the coupling reaction carried out with appropriate yields for both electron-rich and electron-deficient aryl halides. The coupling reaction completed in water as a green solvent. The catalyst was also recycled for four runs with a small decrease in its catalytic activity. The presented new method allows an easier and more cost-efficient synthesis of biaryls from the reaction of arylboronic acids with various aryl halides in water.

Room Temperature C-H Arylation of Benzofurans by Aryl Iodides

A robust method of room temperature direct arylation for benzofuran is reported. This discovery allows for mild arylation by commercially available aryl iodides with complete C-2 regioselectivity and tolerates a range of functional groups, including heat sensitive groups. Mechanistically, a Heck-type oxyarylation product from a direct arylation process is reported as a key piece of evidence for a carbopalladation intermediate.

One-pot Tandem Heck alkynylation/cyclization reactions catalyzed by Bis(Pyrrolyl)pyridine based palladium pincer complexes

Ligand assisted palladium catalyzed one-pot tandem Heck alkynylation/cyclization reactions for the synthesis of benzofurans was reported in this paper. Well-defined palladium-pincer complexes exhibited excellent catalytic activities for the one-pot tandem Heck alkynylation/cyclization reactions yielding benzofuran derivatives using 0.1 molpercent catalyst. All the catalytic reactions are performed in air. The effects of variables such as solvents, the temperature on the catalytic activity are also reported. High product conversion was obtained for differently substituted 2-iodophenol at 120 °C in 10 h.

Palladium complexes with an annellated mesoionic carbene (MIC) ligand: Catalytic sequential Sonogashira coupling/cyclization reaction for one-pot synthesis of benzofuran, indole, isocoumarin and isoquinolone derivatives

Two Pd(ii) complexes (1 and 2) featuring a fused π-conjugated imidazo[1,2-a][1,8]naphthyridine-based mesoionic carbene ligand have been synthesized and structurally characterized. Both complexes effectively catalyze the one-pot synthesis of benzofuran starting from phenylacetylene and 2-iodophenol under mild conditions. Complex 1 is found to be an excellent catalyst for the straightforward access to a library of benzofuran, indole, isocoumarin and isoquinolone derivatives by the reaction of terminal alkynes with 2-iodo derivates of phenol, N-methyl aniline, benzoic acid and N-methyl benzamide, respectively. The general utility of the catalytic method is demonstrated using a variety of diversely substituted terminal alkynes and the corresponding desired products are obtained in good to excellent yields. On the basis of control experiments, a two-cycle mechanism is proposed which involves the Sonogashira coupling of 2-iodo derivatives with alkynes and the subsequent cyclization of the corresponding 2-alkynyl compounds.

Method for synthesizing 2-aryl benzofuran and derivatives thereof

The invention relates to a method for synthesizing 2-aryl benzofuran and derivatives thereof. According to the method, cheap and easily available 2, 3-dihydrobenzofuran compounds, an organic boron reagent and bromo-aromatic hydrocarbon are taken as raw materials, and a two-step cascade reaction is carried out under mild conditions, so that the 2-aryl benzofuran product can be conveniently prepared. At present, the reported synthesis methods of 2-aryl benzofuran and derivatives thereof mainly have the problems of long synthesis route, expensive raw materials, harsh reaction conditions and the like. Compared with reported methods, the synthesis method has the advantages of specific reaction selectivity, short reaction route and the like, and a convenient and efficient synthesis strategy is provided for laboratory preparation or industrial production of 2-arylbenzofuran products.

PALLADIUM ACYCLIC DIAMINOCARBENE COMPLEXES AS PRECATALYSTS FOR HIYAMA COUPLING AND THE TANDEM ONE-POT FLUORIDE FREE HIYAMA COUPLING/CYCLIZATION FOR THE SYNTHESIS OF BIOLOGICALLY RELEVANT

The present invention provides Acyclic diaminocarbene complex of formula (I): Wherein, M is palladium; X is monoanionic ligand selected from Cl, Br or I; Where R1 is different from R2; R1 is selected from the group consisting of alkyl or aryl, each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms; R2 is selected from the group consisting of alkyl, or aryl each of which have 4 to 20 carbon atoms, and may optionally contain one or more heteroatoms. The said palladium diamino carbine complex of the present invention are particularly useful as catalyst from Hiyama cross-coupling reaction.

Transition-Metal-Free Synthesis of Heterobiaryls through 1,2-Migration of Boronate Complex

The synthesis of a diverse range of heterobiaryls has been achieved by a transition-metal-free sp2–sp2 cross-coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.

Direct suzuki-miyaura coupling with naphthalene-1,8-diaminato (dan)-substituted organoborons

The actually direct Suzuki-Miyaura coupling with "protected" R-B(dan) (dan = naphthalene-1,8-diaminato) was demonstrated to smoothly occur without in situ deprotection of the B(dan) moiety. The use of t-BuOK (Ba(OH)2 in some cases) as a base under anhydrous conditions is the key to the successful cross-coupling, where R-B(dan) is readily converted into a transmetalation-active borate-form, regardless of the well-accepted diminished boron-Lewis acidity.

Ligand-Free Pd-Catalyzed Synthesis of 3-Allylbenzofurans by Merging Decarboxylative Allylation and Nucleophilic Cyclization

A new single Pd-catalyzed decarboxylative allylation-nucleophilic cyclization relay is reported by using α-alkynyl arylols and vinylethylene carbonates (or vinyl carbamates), and a wide range of 3-allyl benzofurans with generally good yields were stereoselectively synthesized under mild conditions, among which the complete stereoselectivity of some cases was also observed. Notably, the present catalysts can tolerate air conditions without any ligand, additive, or base, opening new avenues to build up oxa-heterocycle frameworks through catalytic difunctionalization of internal alkynes.