80079-25-0

Basic information

• Product Name: 2-Ethyl-3-methylbenzofuran
• Synonyms: 2-Ethyl-3-methylbenzofuran;Benzofuran, 2-ethyl-3-methyl-
• CAS NO: 80079-25-0
• Molecular Formula: C11H12O
• Molecular Weight: 160.21
• Product Categories: Heterocycles;Heterocyclic Compound
• Mol File: 80079-25-0.mol

Chemical Properties

• Boiling Point: 240 °C
• Flash Point: 97 °C
• Appearance: /
• Density: 1.030
• Refractive Index: 1.566
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Ethyl-3-methylbenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethyl-3-methylbenzofuran(80079-25-0)
• EPA Substance Registry System: 2-Ethyl-3-methylbenzofuran(80079-25-0)

Safety Data

• Hazardous Substances Data: 80079-25-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H12O/c1-3-10-8(2)9-6-4-5-7-11(9)12-10/h4-7H,3H2,1-2H3

Upstream product

• 91970-24-0 3-Phenoxy-pentanon-⁽²⁾ 
• 815-48-5 3-bromopentan-2-one 
• 108-95-2 phenol 
• 97139-96-3 2'-propanoyloxyacetophenone 
• 90-02-8 salicylaldehyde 
• 1646-26-0 1-(benzo[b]furan-2-yl)ethanone 
• 3131-63-3 2-ethylbenzofuran 
• 19244-42-9 2-allyloxystyrene 
• 553380-60-2 3-pentanone O-phenyloxime 
• 6092-80-4 phenoxyamine hydrochloride 
• 96-22-0 pentan-3-one 
• 10035-41-3 2-ethylbenzofuran-3-carbaldehyde 

Relevant articles and documents

NEW METHOD FOR THE REDUCTION OF BENZOFURANS

A new method for the reduction of benzofurans with potassium and sodium borohydrides in CF3COOH was developed.It is shown by gas-liquid chromatography and PMR spectroscopy that mixtures (ca. 2:3) of the cis and trans isomers of dihydro derivatives of benzofuran are formed in the reduction.The mechanism of the reduction includes intermolecular transfer of a hydride ion to the protonated form of the benzofuran.

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.

Short communication: Titanium-induced synthesis of benzofurans

Ketoesters derived from the acylation of o-hydroxyacetophenone with aliphatic as well as aromatic acid chlorides undergo intramolecular cyclization in the presence of low-valent titanium to afford benzofurans in good yields. The reduction of titanium trichloride with dry zinc powder in refluxing THF takes place in the presence of the ketoester which simultaneously cyclizes as the titanium catalyst is formed, rendering the pre-reduction of titanium trichloride in a separate step unnecessary.

Direct preparation of benzofurans from O-arylhydroxylamines

Reaction of O-arylhydroxylamine hydrochlorides with either cyclic or acyclic ketones in the presence of methanesulfonic acid leads directly to the benzofuran derivative via a proposed one-pot condensation-rearrangement- cyclisation reaction sequence in good to excellent yields. Georg Thieme Verlag Stuttgart.

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans

A new synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic or acyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP system is found to be the most effective for constructing various benzofurans. Synthetic utility of this reaction is demonstrated by the short synthesis of natural benzofurans without protection of the hydroxy group. The synthesis of Stemofuran A was accomplished via condensation of ketones with aryloxyamine and subsequent reaction with TFAT-DMAP in a four-step synthesis with 72% overall yield. Similarly, Eupomatenoid 6 and Coumestan were synthesized through the reaction of oxime ether with TFAT-DMAP. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Cycloisomerization promoted by the combination of a ruthenium-carbene catalyst and trimethylsilyl vinyl ether, and its application in the synthesis of heterocyclic compounds: 3-Methylene-2,3-dihydroindoles and 3-methylene-2,3- dihydrobenzofurans

Substituted N and O heterocycles have been synthesized by the cycloisomerization of dienes using a ruthenium-carbene catalyst. The products obtained with and without trimethylsilyl vinyl ether differ (see scheme, Cy = cyclohexyl, Mes = 2,4,6-trimethylphenyl, Ts = p-toluenesulfonyl).

Efficient [3,3]-sigmatropic rearrangement accelerated by a trifluoroacetyl group: Synthesis of benzofurans under mild conditions

The [3,3]-sigmatropic rearrangement took place smoothly during the course of trifluoroacetylation of O-phenyl-oxime at below room temperature to give the dihydrobenzofuran or benzofuran as a result of concomitant cyclization.