13391-28-1

Basic information

• Product Name: 5-Methoxybenzofuran
• Synonyms: 5-METHOXYBENZOFURAN;5-methoxy-benzofura;Benzofuran, 5-methoxy-;5-methoxy-1-benzofuran;5-Methoxybenzo[b]furan
• CAS NO: 13391-28-1
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.16
• Mol File: 13391-28-1.mol

Chemical Properties

• Melting Point: 31 °C
• Boiling Point: 123 °C
• Flash Point: 99.13 °C
• Appearance: /
• Density: 1.137 g/cm³
• Vapor Pressure: 0.181mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Methoxybenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxybenzofuran(13391-28-1)
• EPA Substance Registry System: 5-Methoxybenzofuran(13391-28-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 13391-28-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 19, p. 257, 1989 DOI: 10.1080/00397918908050977

InChI:InChI=1/C9H8O2/c1-10-8-2-3-9-7(6-8)4-5-11-9/h2-6H,1H3

Upstream product

• 68426-09-5 (4-methoxyphenoxy)acetaldehyde 
• 5394-57-0 2-(4-methoxyphenoxy)ethanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 23145-07-5 5-bromobenzofuran 
• 38050-71-4 9-methoxy-9-BBN 
• 33320-42-2 5-methoxy-2,3-dihydro-benzofuran-3-ol 
• 75717-53-2 2-chloro-1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 13196-10-6 benzofuran-5-ol 
• 74-88-4 methyl iodide 
• 935-50-2 4,4-dimethoxycyclohexa-2,5-dienone 
• 68426-08-4 1-(2,2-dimethoxyethoxy)-4-methoxybenzene 
• 93198-67-5 methyl (E)-3-(2-hydroxy-5-methoxyphenyl)acrylate 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 865759-99-5 2-allyl-1-(2-chloroethoxy)-4-methoxybenzene 

Downstream Products

• 36826-30-9 4-bromo-5-methoxybenzofuran 
• 551001-79-7 (5-methoxy-1-benzofuran-2-yl)boronic acid 

Relevant articles and documents

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.

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.

STABLE SOLID DISPERSIONS OF B-RAF KINASE DIMER INHIBITOR, METHODS OF PREPARATION, AND USES THEREFOR

Disclosed herein is a physically stable solid dispersion comprising Compound 1, i.e., the B-RAF kinase dimer inhibitor 1- ( (1S, 1aS, 6bS) -5- ( (7-oxo-5, 6, 7, 8-tetrahydro-1, 8-naphthyridin-4-yl) oxy) -1a,6b-dihydro-1H-cyclopropa [b] benzofuran-1-yl) -3- (2, 4, 5-trifluorophenyl) urea and a specific stabilizing polymer, the method for preparing the same, and the uses of the solid dispersion. Also disclosed herein is the crystalline form of Compound 1.

Method suitable for large-scale production of B-RAF kinase dimer inhibitor

The invention relates to a method for large-scale production of a B-RAF kinase dimer inhibitor 1-((1S, 1aS, 6bS)-5-((7-oxo-5, 6, 7, 8-tetrahydro-1, 8-diazanaphthalene-4-yl) oxy)-1a, 6b-dihydro-1H-cyclopropyl [b] benzofuran-1-yl)-3-(2, 4, 5- trifluorophenyl) urea (hereinafter sometimes referred to as a compound 1). The method enables impurities or by-products to be controlled to 0.05% or less without the use of expensive column chromatography operations. Thus, the method greatly reduces cost and is suitable for large-scale production.

Stable crystalline form A of B-RAF kinase dimer inhibitor

The invention relates to a stable crystalline form A of a B-RAF kinase dimer inhibitor 1-((1S, 1aS, 6bS)-5-((7-oxo-5, 6, 7, 8-tetrahydro-1, 8-diazanaphthalene-4-yl) oxy)-1a, 6b-dihydro-1H-cyclopropyl[b] benzofuran-1-yl)-3-(2, 4, 5- trifluorophenyl) urea (hereinafter sometimes referred to as a compound 1), a preparation method of the crystalline Form A and therapeutic use of the crystalline Form A.

Amorphous B-RAF kinase dimer inhibitor

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New heteroaryl carbamates: Synthesis and biological screening in vitro and in mammalian cells of wild-type and mutant HIV-protease inhibitors

New heteroaryl HIV-protease inhibitors bearing a carbamoyl spacer were synthesized in few steps and high yield, from commercially available homochiral epoxides. Different substitution patterns were introduced onto a given isopropanoyl-sulfonamide core that can have either H or benzyl group. The in vitro inhibition activity against recombinant protease showed a general beneficial effect of both carbamoyl moiety and the benzyl group, ranging the IC50 values between 11 and 0.6 nM. In particular, benzofuryl and indolyl derivatives showed IC50 values among the best for such structurally simple inhibitors. Docking analysis allowed to identify the favorable situation of such derivatives in terms of number of interactions in the active site, supporting the experimental results. The inhibition activity was also confirmed in HEK293 mammalian cells and was maintained against protease mutants. Furthermore, the metabolic stability was comparable with that of the commercially available inhibitors.

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