20492-07-3

Basic information

• Product Name: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE
• Synonyms: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE;2-(furan-2-yl)-4H-3,1-benzoxazin-4-one
• CAS NO: 20492-07-3
• Molecular Formula: C₁₂H₇NO₃
• Molecular Weight: 213.18888
• Mol File: 20492-07-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 326°C at 760 mmHg
• Flash Point: 151°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 0.000221mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE(20492-07-3)
• EPA Substance Registry System: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE(20492-07-3)

Safety Data

• Hazardous Substances Data: 20492-07-3(Hazardous Substances Data)

Usage

Naturally occurring compound

DIMBOA is a compound that occurs naturally in certain plants, particularly in the grass family.

Plant defense against pests and diseases

DIMBOA plays a role in plant defense against pests and diseases, due to its strong anti-microbial and anti-feedant properties.

Agricultural applications

DIMBOA has been studied for its potential use in agriculture, as it has shown promise in controlling pests and improving crop yields.

Pharmaceutical potential

DIMBOA has been investigated for its potential use in pharmaceuticals, due to its anti-inflammatory and antioxidant properties.

Versatile compound

DIMBOA is a versatile compound with potential applications in both agriculture and medicine.

InChI:InChI=1/C12H7NO3/c14-12-8-4-1-2-5-9(8)13-11(16-12)10-6-3-7-15-10/h1-7H

Upstream product

• 1431098-07-5 C₁₂H₈INO₃ 
• 50-00-0 formaldehyd 
• 19771-81-4 furan-2-carboxylic acid 2-bromoanilide 
• 527-69-5 2-furancarbonyl chloride 
• 615-36-1 2-bromoaniline 
• 551-93-9 2-aminoacetophenone 
• 1875-58-7 N-(2-acetylphenyl)furan-2-carboxamide 
• 17698-14-5 furan-2-carboxylic acid hydroxyamide 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 1373758-56-5 3-(furan-2-yl)-5H-1,4,2-dioxazol-5-one 
• 201230-82-2 carbon monoxide 
• 615-43-0 2-iodophenylamine 
• 144223-33-6 2-furoyl-1H-1,2,3-benzotriazole 
• 529-23-7 o-aminobenzaldehyde 

Downstream Products

• 329067-78-9 N-(2-(p-tolyl-carbamoyl)phenyl)furan-2-carboxamide 
• 1310340-98-7 2-(furan-2-yl)-3-(phenylamino)quinazolin-4(3H)-one 
• 1310340-99-8 N-{2-[(4-sulfamoylphenyl)carbamoyl]phenyl}furan-2-carboxamide 

Relevant articles and documents

Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source

A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.

Recyclable Heterogeneous Palladium-Catalyzed Cyclocarbonylation of 2-Iodoanilines with Acyl Chlorides in the Biomass-Derived Solvent 2-Methyltetrahydrofuran

A highly efficient, green palladium-catalyzed cyclocarbonylation of 2-iodoanilines with acyl chlorides has been developed that proceeds smoothly in a biomass-derived solvent 2-methyltetrahydrofuran with N,N-diisopropylethylamine as base at 100 °C under 20 bar of carbon monoxide using an 2-aminoethylamino-modified MCM-41-anchored palladium acetate complex [2N-MCM-41-Pd(OAc)2] as a heterogeneous catalyst, yielding a wide variety of 2-substituted 4H-3,1-benzoxazin-4-one derivatives in good to excellent yields. This supported palladium catalyst could be facilely obtained by a two-step procedure from easily available starting materials and readily recovered via a simple filtration process and recycled at least 8 times without any apparent decrease in catalytic efficiency. The developed methodology not only avoids the use of toxic solvents such as tetrahydrofuran and dimethylformamide but also solves the basic problem of expensive palladium catalyst recovery and reuse and prevents effectively palladium contamination of the desired product.

Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation

A palladium-catalyzed chelation-assisted selective ortho C-H bond olefination of biologically active 4H-benzo[d][1,3] oxazin-4-one derivatives with activated olefins has been achieved. The products are obtained in good yields with high regio- and stereose