42926-53-4

Basic information

• Product Name: Benzofuran, 2-(2-methoxyphenyl)-
• CAS NO: 42926-53-4
• Molecular Formula: C15H12O2
• Molecular Weight: 224.259
• Mol File: 42926-53-4.mol

Chemical Properties

• CAS DataBase Reference: Benzofuran, 2-(2-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzofuran, 2-(2-methoxyphenyl)-(42926-53-4)
• EPA Substance Registry System: Benzofuran, 2-(2-methoxyphenyl)-(42926-53-4)

Safety Data

• Hazardous Substances Data: 42926-53-4(Hazardous Substances Data)

Upstream product

• 273720-79-9 (E)-2-methoxy-α-(2-methoxyphenyl)cinnamic acid 
• 89122-68-9 2-[2-(2-methoxyphenyl)vinyl]phenol 
• 5293-78-7 2,2'-dimethoxytolane 
• 271-89-6 1-benzofurane 
• 766-51-8 2-Chloroanisole 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 54008-77-4 2-bromo-1-benzofuran 
• 150-76-5 4-methoxy-phenol 
• 529-28-2 4-iodoanisol 
• 90-02-8 salicylaldehyde 
• 90-01-7 salicylic alcohol 
• 70340-04-4 (2-hydroxybenzyl)triphenylphosphonium bromide 
• 21615-34-9 2-Methoxybenzoyl chloride 

Relevant articles and documents

B(C6F5)3-Catalyzed Hydroarylation of Aryl Alkynes for the Synthesis of 1,1-Diaryl and Triaryl Substituted Alkenes

A new strategy for the synthesis of 1,1-diaryl and triarylsubstituted alkenes has been developed utilizing B(C6F5)3-catalyzed hydroarylation of alkynes with phenols. The method provides a direct route to ortho-alkenylated phenols with both terminal and internal alkynes. The reactions show excellent regioselectivity, and good stereoselectivity was observed for the hydroarylation of internal alkynes. Computational and experimental studies suggest that for the reaction of internal alkynes and phenols, an acid-catalyzed isomerization mechanism involving two tertiary carbonium ion intermediates is responsible for the formation of Z-triaryl substituted alkenes.

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.

Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents

A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Synthesis and in vitro study of nitro- and methoxy-2-phenylbenzofurans as human monoamine oxidase inhibitors

A new series of 2-phenylbenzofuran derivatives were designed and synthesized to determine relevant structural features for the MAO inhibitory activity and selectivity. Methoxy substituents were introduced in the 2-phenyl ring, whereas the benzofuran moiety was not substituted or substituted at the positions 5 or 7 with a nitro group. Substitution patterns on both the phenyl ring and the benzofuran moiety determine the affinity for MAO-A or MAO-B. The 2-(3-methoxyphenyl)-5-nitrobenzofuran 9 was the most potent MAO-B inhibitor (IC50 = 0.024 μM) identified in this series, whereas 7-nitro-2-phenylbenzofuran 7 was the most potent MAO-A inhibitor (IC50 = 0.168 μM), both acting as reversible inhibitors. The number and position of the methoxyl groups on the 2-phenyl ring, have an important influence on the inhibitory activity. Molecular docking studies confirmed the experimental results and highlighted the importance of key residues in enzyme inhibition.

Synthesis of benzofurans from terminal alkynes and iodophenols catalyzed by recyclable palladium nanoparticles supported on N,O-dual doped hierarchical porous carbon under copper- and ligand-free conditions

We herein report that a stable and recyclable heterogeneous catalyst, consisting of Pd nanoparticles supported on N,O-dual doped hierarchical porous carbon derived from naturally available and renewable biomass-bamboo shoots, which allows for highly efficient one-pot tandem reaction of o-iodophenols with terminal alkynes to synthesize biologically active 2-benzofuran derivatives under copper- and ligand-free conditions. The catalyst performed superior catalytic performance compared with the analogous Pd/C and supported on other metal oxides under otherwise identical conditions. A broad set of aryl and alkyl terminal alkynes can be effectively coupled /cyclized with various o-iodophenols to afford their corresponding 2-benzofurans in good to high yields with good tolerance of multiple functional groups. Moreover, the catalyst showed good stability and could be reused several times without significant loss of activity.

Visible light mediated desilylative C(sp2)-C(sp2) cross-coupling reactions of arylsilanes with aryldiazonium salts under Au(i)/Au(iii) catalysis

Desilylative C(sp2)-C(sp2) cross-coupling reactions of arylsilanes with aryldiazonium salts under Au(i)/photoredox catalysis have been reported. The addition of Cu-salts as catalysts was found to be crucial for the success of this tr

Unexpected one-step synthesis of 3-benzoyl-2-phenylbenzofurans under Wittig conditions

The reaction of 2-hydroxybenzyltriphenylphosphonium bromide with substituted benzoyl chlorides under Wittig conditions, led to 2-phenylbenzofuran derivatives 4a–p and the unexpected formation of 3-benzoyl-2-phenylbenzofuran derivatives 5a–p. Benzoyl chlorides possessing electron-withdrawing groups afforded 3-benzoyl-2-phenylbenzofuran derivatives in higher yields than those with electron-donating groups. This reaction represents a simple and regioselective, one-pot route towards the preparation of deactivated 3-benzoyl-2-phenylbenzofuran compounds which are difficult to obtain by the direct acylation of 2-phenylbenzofurans.

1,2,3-Triazole based bisphosphine, 5-(diphenylphosphanyl)-1-(2-(diphenylphosphanyl)-phenyl)-4-phenyl-1: H -1,2,3-triazole: An ambidentate ligand with switchable coordination modes

The reaction of 1-(2-bromophenyl)-4-phenyl-1H-1,2,3-triazole (1) with Ph2PCl yielded bisphosphine, 5-(diphenylphosphanyl)-1-(2-(diphenylphosphanyl)phenyl)-4-phenyl-1H-1,2,3-triazole (2). Bisphosphine 2 exhibits ambidentate character in either the κ2-P,N or κ2-P,P coordination mode. Treatment of 2 with [M(CO)4(piperidine)2] (M = Mo and W) yielded κ2-P,N and κ2-P,P coordinated Mo0 and W0 complexes [M(CO)4(2)] [M = W-κ2-P,N (4); Mo-κ2-P,P (5); W-κ2-P,P (6)] depending on the reaction conditions. Formation and stability of κ2-P,P coordinated Mo0 and W0 complexes were assessed by time dependent 31P{1H} NMR experiments and DFT studies. The complex 4 on treatment with [AuCl(SMe2)] afforded the hetero-bimetallic complex [μ-PN,P-{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2AuCl)}-κ2-P,N}W(CO)4] (7). The 1:1 reaction between 2 and [CpRu(PPh3)2Cl] yielded [(η5-C5H5)RuCl{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}}-κ2-P,P] (8), whereas the similar reaction with [Ru(η6-p-cymene)Cl2]2 in a 2:1 molar ratio produced a cationic complex [(η6-p-cymene)RuCl{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}}-κ2-P,N]Cl (9). Similarly, treatment of 2 with [M(COD)(Cl)2] (M = Pd and Pt) in a 1:1 molar ratio yielded PdII and PtII complexes [{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}-κ2-P,P}PdCl2] (10) and [{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}-κ2-P,P}PtCl2] (11). The reaction of 2 with 2 equiv. of [AuCl(SMe2)] afforded [Au2Cl2{o-Ph2P(C6H4){1,2,3-N3C(Ph)C(PPh2)}}-μ-P,P] (12). Most of the complexes have been structurally characterized. Palladium complex 10 shows excellent catalytic activity towards Cu-free Sonogashira alkynylation/cyclization reactions.

Fluorination of 2-substituted benzo[b]furans with Selectfluor

An efficient protocol was developed to access 3-fluoro-2-hydroxy-2-substituted benzo[b]furans with Selectfluor as the fluorinating reagent in MeCN and water. By utilizing SOCl2/Py as the dehydrating agent, the compounds above were readily conve

N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed Direct C-H Bond Arylation of Benzo[b]furans with Aryl Chlorides

The first example of sole direct C-H bond arylation of benzo[b]furans with aryl chlorides was achieved catalyzed by a well-defined NHC-Pd(II)-Im complex. Under the suitable conditions, all reactions involving kinds of benzo[b]furans and (hetero)aryl chlor