21535-97-7

Basic information

• Product Name: 3-Methylbenzofuran
• Synonyms: RARECHEM AM LA 0012;3-METHYLBENZO[B]FURAN;3-METHYLBENZOFURAN;3-Methylbenzofurane;3-METHYL-1-BENZOFURAN;3-Methylbenzofuran, GC 98%;3-Methylbenzofuran,98%;3-Methylbenzofuran, 98% 1GR
• CAS NO: 21535-97-7
• Molecular Formula: C₉H₈O
• Molecular Weight: 132.16
• EINECS: 244-427-2
• Product Categories: Furans, Benzofurans & Dihydrobenzofurans;Furans, Benzofurans & Dihydrobenzofurans
• Mol File: 21535-97-7.mol

Chemical Properties

• Boiling Point: 75°C/14mm
• Flash Point: 73.2 °C
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.046 g/mL at 25 °C
• Vapor Pressure: 0.608mmHg at 25°C
• Refractive Index: 1.5535-1.5555
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Methylbenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methylbenzofuran(21535-97-7)
• EPA Substance Registry System: 3-Methylbenzofuran(21535-97-7)

Safety Data

• Hazard Codes: T,Xn
• Statements: 10-41-22
• Safety Statements: 24/25-39-26
• RIDADR: 1993
• WGK Germany: 3
• Hazardous Substances Data: 21535-97-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Methylbenzofuran is used as a key intermediate in the enantioselective preparation of benzoheterocycles. This application is particularly relevant in the field of pharmaceuticals and organic chemistry, where the synthesis of chiral molecules with specific stereochemistry is of great importance.
Used in Enantioselective Synthesis:
In the enantioselective synthesis of benzoheterocycles, 3-Methylbenzofuran serves as a valuable starting material. The enantioselective preparation of these compounds is crucial for the development of new drugs and pharmaceuticals, as the stereochemistry of a molecule can significantly influence its biological activity and efficacy.
Used in Iridium-Catalyzed Hydrogenation:
3-Methylbenzofuran is utilized in the iridium-catalyzed hydrogenation of indole and benzofuran derivatives. This process is an essential step in the synthesis of various biologically active compounds and has applications in the fields of medicinal chemistry and drug discovery.
Used in Pharmaceutical Industry:
The enantioselective preparation of benzoheterocycles using 3-Methylbenzofuran is particularly relevant in the pharmaceutical industry. These synthesized compounds can be used as potential drug candidates, targeting various diseases and medical conditions.
Used in Research and Development:
3-Methylbenzofuran is also used in research and development for the exploration of new synthetic routes and methodologies in organic chemistry. Its unique chemical properties make it an interesting compound for studying reaction mechanisms and developing novel catalytic systems.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 5588, 1995 DOI: 10.1021/jo00122a046Tetrahedron Letters, 27, p. 2303, 1986 DOI: 10.1016/S0040-4039(00)84514-1

InChI:InChI=1/C9H8O/c1-3-8-4-6-9(10-2)7-5-8/h1,4-7H,2H3

Upstream product

• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 917-64-6 methyl magnesium iodide 
• 24673-56-1 3-methyl-1-benzofuran-2-carboxylic acid 
• 88-69-7 2-(1-methylethyl)phenol 
• 36638-16-1 2,3-dihydro-3-methylenebenzofuran 
• 63815-27-0 2-(2'-acetylphenoxy)acetic acid ethyl ester 
• 24892-63-5 1-allyloxy-2-iodobenzene 
• 60333-75-7 O-allyl-2-bromophenol 
• 41876-99-7 1-iodo-2-(2-propynyloxy)benzene 
• 81500-61-0 o-allyloxyphenylmercury chloride 
• 38770-76-2 1-bromo-2-(prop-2-yn-1-yloxy)benzene 
• 167558-60-3 1,1-Dichloro-2-(o-hydroxyphenyl)propene 
• 167558-56-7 1,1-Dibromo-2-(o-hydroxyphenyl)propene 
• 621-87-4 3-phenoxy-2-propanone 

Downstream Products

• 118-93-4 o-hydroxyacetophenone 
• 67382-14-3 2-Bromo-1-(3-methylbenzofuran-2-yl)ethanone 
• 127776-71-0 2-(3-methoxyphenyl)-3-methylbenzofuran 
• 79517-74-1 2-(o-methoxyphenyl)-3-methylbenzofuran 
• 23911-56-0 2-acetyl-3-methylbenzofuran 
• 128753-83-3 2a,7b-Dihydro-7b-methyl-1,2-dioxeto<3,4-b>benzofuran 
• 87977-35-3 methyl-3 nitro-2 benzofuranne 
• 159588-09-7 2-(methoxyphenylmethyl)-3-methylbenzofuran 
• 4687-25-6 1-benzofuran-3-carbaldehyde 
• 134940-29-7 3-methyl-3H-benzofuran-2-one 
• 4687-23-4 3-hydroxymethylbenzofuran 
• 1001421-88-0 6-(4-tert-butylphenyl)-5-(4-(5,5-dimethyl-1,3-dioxan-2-yl)but-1-enyl)-1-(3-methylbenzofuran-2-yl)butyl)-4-ethyl-2H-pyran-2-one 
• 1189752-75-7 N,N-dimethyl-4,4-bis(3-methylbenzofuran-2-yl)-1-phenylcyclohexanamine 
• 38281-49-1 3-bromomethylbenzofuran 

Relevant articles and documents

Electrochemical Intramolecular Reductive Cyclisation Catalysed by Electrogenerated Ni(cyclam)(2+)

The intramolecular cyclisation of a series of o-halogenated aromatic compounds containing unsaturated side-chains has been developed using electrosynthesis, combined with organometallic catalysis by Ni(cyclam)Br2.

Synthesis of benzofurans in ionic liquid by a PdCl2-catalyzed intramolecular Heck reaction

PdCl2-catalyzed intramolecular Heck reaction was conducted in ionic liquid, 1-n-butyl-3-methylimidazolium tetraborate ([BMIm] BF4), substituted benzofurans were obtained in modest to satisfactory yields. The ionic liquid containing Pd catalyst can be used four times with a little loss of activity.

The Synthesis of 3-Methylene-2,3-dihydrobenzofuran Stabilised as its Tricarbonylchromium Complex

The title complex has been synthesised in two steps by the palladium-catalysed coupling of o-lithiated η6-fluorobenzenetricarbonylchromium(0) with 2-bromo-1-trimethylsiloxyprop-2-ene and cyclisation of the product with fluoride ion.

Electrochemical partial fluorination of organic compounds. 74. Efficient anodic synthesis of 2-fluoro- and 2,3-difluoro-2,3-dihydrobenzofuran derivatives

Anodic fluorination of 3-substituted benzofuran derivatives in a variety of fluoride salts resulted in the formation of three fluorinated products; two stereoisomers of 2,3-difluoro-2,3-dihydrobenzofuran (cis and trans) and cis-2-fluoro-3-hydroxy-2,3-dihydrobenzofuran derivatives. Dehydrofluorination of the main products, cis-difluoro derivatives, furnished the nonaromatic 2-fluoro-3-benzofuranyledene derivatives instead of the aromatic 2-fluorobenzofuran derivatives.

Enantio- and Diastereoselective, Complete Hydrogenation of Benzofurans by Cascade Catalysis

We report an enantio- and diastereoselective, complete hydrogenation of multiply substituted benzofurans in a one-pot cascade catalysis. The developed protocol facilitates the controlled installation of up to six new defined stereocenters and produces architecturally complex octahydrobenzofurans, prevalent in many bioactive molecules. A unique match of a chiral homogeneous ruthenium-N-heterocyclic carbene complex and an in situ activated rhodium catalyst from a complex precursor act in sequence to enable the presented process.

Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening

The generation of metal carbenoids via ring opening of cyclopropenes by transition metals offers a simple entry into highly reactive intermediates. Herein, we describe a diastereoselective intermolecular rhodium-catalyzed cyclopropanation of heterocycles and alkenes using cyclopropenes as carbene precursors with a low loading of a commercially available rhodium catalyst. The reported method is scalable and could be performed with catalyst loadings as low as 0.2 mol %, with no impact to the reaction yield or selectivity.

Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent

Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.

Mercapto-amide boronic acid derivative and application thereof as MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase) inhibitor

The invention provides a compound of a formula (I) shown in the specification, or a conformational isomer, or an optical isomer or a pharmaceutically acceptable salt thereof. The compound of the formula (I) shown in the specification has excellent broad-spectrum inhibitory activity on MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase), and can be used for preparing MBL and/or SBL inhibitors. Moreover, the compound disclosed by the invention has excellent antibacterial activity on multiple drug-resistant bacteria and is capable of reversing drug resistance of carbapenem drug-resistant bacteria, and the antibacterial effect of the compound is prior to those of positive control products such as L-captopril and tazobactam. The compound disclosed by the invention has very great potential in preparation of MBL/SBL dual inhibitors and medicines reversing drug resistance of carbapenem drug-resistance bacteria.

Structure-based development of (1-(3′-Mercaptopropanamido)methyl)boronic Acid Derived Broad-Spectrum, Dual-Action Inhibitors of Metallo- And Serine-β-lactamases

The emergence and spread of bacterial pathogens acquired metallo-β-lactamase (MBL) and serine-β-lactamase (SBL) medicated β-lactam resistance gives rise to an urgent need for the development of new dual-action MBL/SBL inhibitors. Application of a pharmacophore fusion strategy led to the identification of (2′S)-(1-(3′-mercapto-2′-methylpropanamido)methyl)boronic acid (MS01) as a new dual-action inhibitor, which manifests broad-spectrum inhibition to representative MBL/SBL enzymes, including the widespread VIM-2 and KPC-2. Guided by the VIM-2:MS01 and KPC-2:MS01 complex structures, further structural optimization yielded new, more potent dual-action inhibitors. Selectivity studies indicated that the inhibitors had no apparent inhibition to human angiotensin-converting enzyme-2 and showed selectivity across serine hydrolyases in E. coli and human HEK293T cells labeled by the activity-based probe TAMRA-FP. Moreover, the inhibitors displayed potentiation of meropenem efficacy against MBL- or SBL-positive clinical isolates without apparent cytotoxicity. This work will aid efforts to develop new types of clinically useful dual-action inhibitors targeting MBL/SBL enzymes.

Decarboxylation method for heterocyclic carboxylic acid compounds

The invention relates to a decarboxylation method for heterocyclic carboxylic acid compounds. The method comprises the following steps: dissolving the heterocyclic carboxylic acid compounds in an aprotic polar solvent N,N-dimethylformamide, and performing decarboxylation at 85-150 DEG C with an organic acid as a catalyst. The method in the invention allows the yield of decarboxylation products obtained after a reaction to be higher than the yield of the products obtained through decarboxylation methods in the prior art, and does not need an expensive metal catalyst; and the solvent (DMF) in the present invention is more stable than DMSO, is not prone to decompose at a high temperature, and it can be recycled, so the cost is reduced. The method has the advantages of simple operation process, zero pollution, greenness, environmental protection and excellent application prospect.