7320-53-8

Usage

Uses

Used in Research Applications:
4-Methyldibenzofuran is used as a research compound for the purpose of studying and quantifying levels of airborne polycyclic aromatic hydrocarbons. Its presence in coal tar and its ability to be synthesized in the lab make it a valuable tool in environmental and chemical research.
Used in Environmental Studies:
In environmental studies, 4-Methyldibenzofuran is used as an indicator compound to assess the presence and concentration of polycyclic aromatic hydrocarbons in the atmosphere. This helps in understanding the impact of these compounds on air quality and human health.
Used in Chemical Synthesis:
4-Methyldibenzofuran is used as a starting material or intermediate in the synthesis of other complex organic compounds in the field of organic chemistry. Its unique structure and properties make it a useful building block for the creation of new molecules with potential applications in various industries.
Used in Health and Safety Assessments:
Due to its combustible nature and potential health hazards, 4-Methyldibenzofuran is used in health and safety assessments to determine the necessary precautions and handling procedures for researchers and workers who may come into contact with 4-METHYLDIBENZOFURAN. This ensures the safety of individuals and the environment during its use in research and other applications.

InChI:InChI=1/C13H10O/c1-9-5-4-7-11-10-6-2-3-8-12(10)14-13(9)11/h2-8H,1H3

Upstream product

• 66283-58-7 6-methyl-1,2,3,4-tetrahydrodibenzo[b,d]furan 
• 128916-10-9 2-Allyloxy-benzoic acid m-tolyl ester 
• 74292-21-0 2,2'-dihydroxy-3-methyl-1,1'-diphenyl 
• 109-72-8 n-butyllithium 
• 132-64-9 dibenzofuran 
• 77-78-1 dimethyl sulfate 
• 128916-11-0 2-Allyloxy-benzoic acid o-tolyl ester 
• 3991-61-5 1-methyl-2-phenoxybenzene 
• 583-55-1 1-Bromo-2-iodobenzene 
• 512-56-1 trimethyl phosphite 
• 912824-85-2 2-(dibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 74-88-4 methyl iodide 
• 51412-72-7 dibenzo-[b,d]furan-4-carbonitrile 
• 1440730-08-4 2-(o-tolyloxy)phenyl pivalate 

Downstream Products

• 96706-46-6 dibenzofuran-4-carbaldehyde 
• 17755-10-1 2-methyl-6-phenylphenol 

Relevant academic research and scientific papers

Palladium-Catalyzed Methylation of Aryl, Heteroaryl, and Vinyl Boronate Esters

A method for the direct methylation of aryl, heteroaryl, and vinyl boronate esters is reported, involving the reaction of iodomethane with aryl-, heteroaryl-, and vinylboronate esters catalyzed by palladium and PtBu2Me. This transformation occurs with a remarkably broad scope and is suitable for late-stage derivatization of biologically active compounds via the boronate esters. The unique capabilities of this method are demonstrated by combining carbon-boron bond-forming reactions with palladium-catalyzed methylation in a tandem transformation.

Trimethylphosphate as a Methylating Agent for Cross Coupling: A Slow-Release Mechanism for the Methylation of Arylboronic Esters

A methyl group on an arene, despite its small size, can have a profound influence on biologically active molecules. Typical methods to form a methylarene involve strong nucleophiles or strong and often toxic electrophiles. We report a strategy for a new, highly efficient, copper and iodide co-catalyzed methylation of aryl- and heteroarylboronic esters with the mild, nontoxic reagent trimethylphosphate, which has not been used previously in coupling reactions. We show that it reacts in all cases tested in yields that are higher than those of analogous copper-catalyzed reactions of MeOTs or MeI. The combination of C-H borylation and this methylation with trimethylphosphate provides a new approach to the functionalization of inert C-H bonds and is illustrated by late-stage methylation of four medicinally active compounds. In addition, reaction on a 200 mmol scale demonstrates reliability of this method. Mechanistic studies show that the reaction occurs by a slow release of methyl iodide by reaction of PO(OMe)3 with iodide catalyst, rather than the typical direct oxidative addition to a metal center. The low concentration of the reactive electrophile enables selective reaction with an arylcopper intermediate, rather than nucleophilic groups on the arylboronate, and binding of tert-butoxide to the boronate inhibits reaction of the electrophile with the tert-butoxide activator to form methyl ether.

A One-Pot Synthesis of Dibenzofurans from 6-Diazo-2-cyclohexenones

A novel and efficient protocol for the rapid construction of dibenzofuran motifs from 6-diazo-2-cyclohexenone and ortho-haloiodobenzene has been developed. The process involves one-pot Pd-catalyzed cross-coupling/aromatization and Cu-catalyzed Ullmann coupling.

Palladium-catalyzed intra-and intermolecular C-H arylation using mesylates: Synthetic scope and mechanistic studies

This paper describes the development of Pd-catalyzed inter-and intramolecular direct arylation using mesylates. Furthermore, a sequential mesylation/arylation protocol using phenols as substrates is described. These transformations are general with respect to the electronics of the C-H substrates and allow for the synthesis of diverse heterocyclic motifs in good yields. Both arenes and heteroarenes efficiently participate in these reactions. Preliminary mechanistic studies are presented for both inter-and intramolecular arylations.

Efficient synthesis of dibenzoxaborininols from diaryl ethers and their application to dibenzofuran synthesis

A convenient and efficient method for the borylation of diaryl ethers leading to dibenzoxaborininols and the synthesis of dibenzofuran derivatives has been developed. The borylation involves the sequential three-step process: lithiation, borylation and hydrolysis. The synthesized dibenzoxaborininols could be readily transformed into dibenzofuran derivatives in good to excellent yields under palladium catalysis in the presence of iodine, and this is the first example for the formation of an aryl C-C bond from diarylborinic acids. Copyright

Competitive pathways in Pd-catalyzed synthesis of arylphenols

Novel developments are described, which have been achieved in the framework of the studies of sequential palladium-catalyzed reactions, involving palladacycle formation with norbornene or norbornadiene via aromatic C-H activation. The use of o-bromophenols as partners of iodobenzenes has led to ring formation after norbornene deinsertion, or to arylphenols, containing a pendant norbornenyl or norbornadienyl group or to vinylarylphenols. The availability of a reductive elimination step drives the reaction course toward a preferential product.

Nickel-catalyzed hydrogenolysis of unactivated carbon-cyano bonds

Selective hydrogenolysis of C-CN bonds can allow chemists to take advantage of ortho-directing ability, α-C-H acidity and electron withdrawing ability of the cyano group for synthetic manipulations. We have discovered hydrogenolysis of aryl and aliphatic cyanides under just 1 bar of hydrogen by using a nickel catalyst. This protocol was applied in the aryl cyanide directed functionalization reaction and α-substitution of benzyl cyanides.

Nickel-catalyzed intramolecular C-H arylation using aryl pivalates as electrophiles

This paper describes a method for nickel catalyzed intramolecular C-H arylation using aryl pivalates as electrophiles. The transformation is efficient for the synthesis of diverse electronically and sterically differentiated dibenzofurans. Additionally, the method could be expanded toward the synthesis of carbazoles. Preliminary mechanistic studies of the transformation are also described.

Novel heteroleptic iridium complexes

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. The disclosed compounds have low sublimation temperatures that allow for ease of purification and fabrication into a variety of OLED devices.

HETEROLEPTIC IRIDIUM COMPLEX

Novel phosphorescent heteroleptic iridium complexes with phenylpyridine and dibenzo-containing ligands are provided. The disclosed compounds have low sublimation temperatures that allow for ease of purification and fabrication into a variety of OLED devices.