17059-52-8

Usage

Uses

Used in Pharmaceutical Industry:
7-Methylbenzofuran is used as a key intermediate in the synthesis of mammalian target of rapamycin (mTOR) inhibitors. These inhibitors are important in the development of drugs for the treatment of various diseases, including cancer, autoimmune disorders, and neurodegenerative conditions. 7-methylbenzofuran plays a crucial role in the production of these therapeutic agents, contributing to their efficacy and potential clinical applications.

InChI:InChI=1/C9H8O/c1-7-3-2-4-8-5-6-10-9(7)8/h2-6H,1H3

Upstream product

• 117516-63-9 1-(2,2-diethoxyethoxy)-2-methylbenzene 
• 95333-18-9 2-methylphenoxyacetaldehyde dimethyl acetal 
• 121045-21-4 6-<2-hydroxy-1-(isopropylthio)ethyl>-o-cresol 
• 95-48-7 ortho-cresol 
• 99179-39-2 (2-methylphenoxy)acetaldehyde 
• 6161-86-0 2-methylphenoxyethanol 
• 95-46-5 2-methylphenyl bromide 
• 110-00-9 furan 
• 534-22-5 2-methylfuran 

Downstream Products

• 50543-55-0 7-methyl-2-phenylbenzofuran 
• 90484-22-3 7-benzofuranylcarboxylic acid 
• 1027281-66-8 4-[4-(7-methyl-benzofuran-2-yl)-4-oxo-butyryl]-benzoic acid methyl ester 

Relevant academic research and scientific papers

CONFORMATIONAL ANALYSIS OF ORGANIC CARBONYL COMPOUNDS. PART 4. A (1)H AND (13)C NUCLEAR MAGNETIC RESONANCE STUDY OF FORMYL AND ACETYL DERIVATIVES OF BENZOFURAN

A conformational study of formyl and acetyl derivatives of benzofuran provides evidence that in the case of 2- and 7-derivatives the E,Z-conformational mixture is solvent dependent, the Z-form prevailing in solvents with higher polarity.The presence of the same substituents in the 3- and 4-position gives compounds with predominantly Z-conformation and no change is caused by solvents.These results show an interestingly different behaviour by carbonyl derivatives of benzofuran with respect to the same benzothiophene derivatives.The conformational analysis was carried out by the n.m.r. method by employing (1)H and (13)C chemical shifts, long-range proton-proton coupling constants, and lanthanide-induced shifts (LIS) simulation.For the derivatives substituted in position 7, the LIS method is not a suitable approach for the determination of the conformer populations since, in solution, a chelate is formed where bonding of Eu to the oxygen atoms of the carbonyl and of the heterocyclic ring stabilizes the Z-form.A quantitative approach for determining the relative conformer populations of benzofuran-7-carbaldehyde was set up by statistical manipulation of long-range proton-proton coupling constants, proton chemical shifts, and the classical of dielectrics.

Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles

A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.

Preparation method of benzofuran compound

The invention relates to a preparation method of a benzofuran compound. The preparation method comprises the following steps: putting a furan compound, acetic acid and a Lewis acid catalyst in a reaction vessel, reacting for 0.5-24 h at 80-160 DEG C, and separating and purifying to obtain the benzofuran compound. According to the preparation method provided by the invention, the furan compound isused as a reaction raw material, an acetic acid water solution is used as a solvent, Lewis acid is used as a catalyst, and at a mild reaction temperature (80-160 DEG C), the benzofuran compound is directly obtained through one-step reaction. The preparation method provided by the invention can synthesize the benzofuran compound with a corresponding structure and functional groups based on the structure and functional groups of the furan compound as a raw material, the raw material components are simple , and the process is convenient to operate; wherein the selectivity of the obtained benzofuran is as high as 99% in the process of synthesizing benzofuran by using furan, so that the method has industrial application prospects.

Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N′-Acyl Arylhydrazines

A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N′-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.

Palladium-Catalyzed Dearomatizing Difunctionalization of Indoles and Benzofurans

A palladium-catalyzed dearomatizing difunctionalization of N-Boc-indoles and benzofurans to give tricyclic indolines and 2,3-dihydrobenzofurans with a fully substituted carbon center is described. Product formation occurs under mild conditions at room temperature with commercially available aryl boronic acids and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as a mild oxidant in good yields. 2-Carboxyalkyl-substituted indoles and benzofurans react under Pd-catalysis with aryl boronic acids and TEMPO through dearomatizing arylation/cyclization to the corresponding indolines and dihydrobenzofurans containing a lactone moiety bearing a fully substituted carbon center.

A Pincer Ruthenium Complex for Regioselective C-H Silylation of Heteroarenes

A pincer Ru(II) catalyst for the highly efficient undirected silylation of O- and S-heteroarenes with (TMSO)2MeSiH and Et3SiH is described, producing heteroarylsilanes with exclusive C2-regioselectivity, good functional-group tolerance, and high turnover numbers (up to 1960). The synthetic utility of the silylated products is demonstrated by Pd-catalyzed Hiyama-Denmark cross-coupling under mild conditions. One-pot, two-step silylation and coupling procedures have been also developed.

OXADIAZINE COMPOUNDS AND METHODS OF USE THEREOF

The present disclosure relates to oxadiazine compounds, pharmaceutical compositions comprising an effective amount of an oxadiazine compound and methods for using an oxadiazine compound in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of an oxadiazine compound.

Copper(ii)-catalyzed C-O coupling of aryl bromides with aliphatic diols: Synthesis of ethers, phenols, and benzo-fused cyclic ethers

A highly efficient copper-catalyzed C-O cross-coupling reaction between aryl bromides and aliphatic diols has been developed employing a cheaper, more efficient, and easily removable copper(ii) catalyst. A broad range of aryl bromides were coupled with aliphatic diols of different lengths using 5 mol% CuCl2 and 3 equivalents of K2CO3 in the absence of any other ligands or solvents to afford the corresponding hydroxyalkyl aryl ethers in good to excellent yields. In this newly developed protocol, aliphatic diols have multilateral functions as coupling reactants, ligands, and solvents. The resulting hydroxyalkyl aryl ethers were further readily converted into the corresponding phenols, presenting a valuable alternative way to phenols from aryl bromides. Furthermore, it was demonstrated that they are useful intermediates for more advanced molecules such as benzofurans and benzo-fused cyclic ethers. This journal is

Discovery of novel and potent retinoic acid receptor α agonists: Syntheses and evaluation of benzofuranyl-pyrrole and benzothiophenyl-pyrrole derivatives

In the course of our studies on retinoic acid receptor (RAR) agonists, we have designed and synthesized a series of benzofuran and benzothiophene derivatives. Some of these compounds (1a,b,e,f,j) markedly inhibited LPS- induced B-lymphocyte proliferation and exerted RARα selectivity. One of them, 4-[5-(4,7-dimethylbenzofuran-2-yl)pyrrol-2-yl]benzoic acid (1b), when orally administered significantly inhibited mouse antibody production and delayed type hypersensitivity (DTH) responses from a dose of 0.1 mg/kg.

PREPARATION AND CYCLIZATION OF ARYLOXYACETALDEHYDE ACETALS; A GENERAL SYNTHESIS OF 2,3-UNSUBSTITUTED BENZOFURANS

A improved method for the preparation of 2,3-unsubstituted benzofurans is described.Specifically, the PPA catalysed cyclization of aryloxyacetaldehyde acetals to give (4-7)-substituted benzofurans has been achieved.