13761-32-5

Basic information

• Product Name: 2-Acetyldibenzofuran
• Synonyms: 2-Acetyldibenzofuran;1-(dibenzo[b,d]furan-2-yl)ethanone;1-(2-dibenzofuranyl)ethanone
• CAS NO: 13761-32-5
• Molecular Formula: C₁₄H₁₀O₂
• Molecular Weight: 210.228
• Mol File: 13761-32-5.mol

Chemical Properties

• Boiling Point: 361.6°Cat760mmHg
• Flash Point: 170.8°C
• Appearance: /
• Density: 1.222g/cm³
• Vapor Pressure: 2.05E-05mmHg at 25°C
• Refractive Index: 1.67
• CAS DataBase Reference: 2-Acetyldibenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetyldibenzofuran(13761-32-5)
• EPA Substance Registry System: 2-Acetyldibenzofuran(13761-32-5)

Safety Data

• Hazardous Substances Data: 13761-32-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Acetyldibenzofuran serves as a valuable building block in organic synthesis, contributing to the creation of a variety of complex organic molecules. Its unique structure allows it to be a key intermediate in the synthesis of pharmaceuticals and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Acetyldibenzofuran is utilized for its potential biological activities. Studies have indicated that it may possess anticancer properties, making it a candidate for further research and development in the context of drug discovery.
Used in Materials Industry:
2-Acetyldibenzofuran's structure and properties also make it suitable for use in the materials industry, where it could be employed in the development of new materials with specific characteristics, such as those with enhanced stability or reactivity.
Used in Fragrance and Flavoring Industry:
2-Acetyldibenzofuran is widely used in the fragrance and flavoring industry due to its aromatic properties. It contributes to the creation of scents and tastes in various consumer products, from perfumes to food items, enhancing the sensory experience of these products.
Used in Antioxidant Applications:
2-Acetyldibenzofuran's antioxidant properties suggest potential uses in applications requiring protection against oxidative stress, which can be beneficial in various industrial processes as well as in health and wellness products.
While 2-Acetyldibenzofuran shows promise in these areas, it is important to note that further research is necessary to fully understand its potential uses and effects, ensuring safety and efficacy in practical applications.

InChI:InChI=1/C14H10O2/c1-9(15)10-6-7-14-12(8-10)11-4-2-3-5-13(11)16-14/h2-8H,1H3

Upstream product

• 132-64-9 dibenzofuran 
• 75-36-5 acetyl chloride 
• 854395-65-6 8-acetyl-dibenzofuran-4-carboxylic acid 
• 144463-66-1 allyl 2-(4-acetylphenoxy)benzoate 
• 5408-56-0 2-iododibenzofuran 
• 74-88-4 methyl iodide 
• 62615-24-1 4'-hydroxy-3'-iodoacetophenone 
• 36039-27-7 2-(4-acetylphenoxy)benzoic acid 
• 16463-38-0 potassium 2-chlorobenzoate 
• 92151-89-8 methyl dibenzo[b,d]furan-4-carboxylate 
• 854395-64-5 8-acetyl-dibenzofuran-4-carboxylic acid methyl ester 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 99-93-4 4-Hydroxyacetophenone 
• 591-50-4 iodobenzene 

Downstream Products

• 109103-97-1 2-bromo-1-dibenzofuran-2-yl-ethanone 
• 1228443-53-5 N-[(4-chlorophenyl)(2-hydroxydibenzofuran-1-yl)methyl]benzamide 
• 1228443-54-6 N-[(2-hydroxydibenzofuran-1-yl)(3,4,5-trimethoxyphenyl)methyl]acetamide 
• 1228443-55-7 N-[(2-hydroxydibenzofuran-1-yl)(3,4,5-trimethoxyphenyl)methyl]benzamide 
• 1228443-56-8 N-[(2-hydroxydibenzofuran-1-yl)(3,4,5-trimethoxyphenyl)methyl]urea 
• 1228443-57-9 N-[(4-bromophenyl)(2-hydroxydibenzofuran-1-yl)methyl]urea 
• 1228443-59-1 N-[(2-hydroxydibenzofuran-1-yl)(4-methoxyphenyl)methyl]acetamide 
• 1228443-60-4 N-[(2-hydroxydibenzofuran-1-yl)(4-methoxyphenyl)methyl]urea 
• 1228443-64-8 1-(4-chlorophenyl)-1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazin-3(2H)-one 
• 1228443-65-9 1-(4-bromophenyl)-1H-benzo[2,3]benzofuro[4,5-e][1,3]oxazin-3(2H)-one 
• 1415391-44-4 C₃₈H₂₈ClN₃O₂ 

Relevant articles and documents

Two-photon uncaging of bioactive thiols in live cells at wavelengths above 800 nm

Photoactivatable protecting groups (PPGs) are useful for a broad range of applications ranging from biology to materials science. In chemical biology, induction of biological processesviaphotoactivation is a powerful strategy for achieving spatiotemporal control. The importance of cysteine, glutathione, and other bioactive thiols in regulating protein structure/activity and cell redox homeostasis makes modulation of thiol activity particularly useful. One major objective for enhancing the utility of photoactivatable protecting groups (PPGs) in living systems is creating PPGs with longer wavelength absorption maxima and efficient two-photon (TP) absorption. Toward these objectives, we developed a carboxyl- and dimethylamine-functionalized nitrodibenzofuran PPG scaffold (cDMA-NDBF) for thiol photoactivation, which has a bathochromic shift in the one-photon absorption maximum fromλmax= 315 nm with the unfunctionalized NDBF scaffold toλmax= 445 nm. While cDMA-NDBF-protected thiols are stable in the presence of UV irradiation, they undergo efficient broad-spectrum TP photolysis at wavelengths as long as 900 nm. To demonstrate the wavelength orthogonality of cDMA-NDBF and NDBF photolysis in a biological setting, caged farnesyltransferase enzyme inhibitors (FTI) were prepared and selectively photoactivated in live cells using 850-900 nm TP light for cDMA-NDBF-FTI and 300 nm UV light for NDBF-FTI. These experiments represent the first demonstration of thiol photoactivation at wavelengths above 800 nm. Consequently, cDMA-NDBF-caged thiols should have broad applicability in a wide range of experiments in chemical biology and materials science.

Nitrodibenzofuran: A One-and Two-Photon Sensitive Protecting Group That Is Superior to Brominated Hydroxycoumarin for Thiol Caging in Peptides

Photoremovable protecting groups are important for a wide range of applications in peptide chemistry. Using Fmoc-Cys(Bhc-MOM)-OH, peptides containing a Bhc-protected cysteine residue can be easily prepared. However, such protected thiols can undergo isomerization to a dead-end product (a 4-methylcoumarin-3-yl thioether) upon photolysis. To circumvent that photoisomerization problem, we explored the use of nitrodibenzofuran (NDBF) for thiol protection by preparing cysteine-containing peptides where the thiol is masked with an NDBF group. This was accomplished by synthesizing Fmoc-Cys(NDBF)-OH and incorporating that residue into peptides by standard solid-phase peptide synthesis procedures. Irradiation with 365 nm light or two-photon excitation with 800 nm light resulted in efficient deprotection. To probe biological utility, thiol group uncaging was carried out using a peptide derived from the protein K-Ras4B to yield a sequence that is a known substrate for protein farnesyltransferase; irradiation of the NDBF-caged peptide in the presence of the enzyme resulted in the formation of the farnesylated product. Additionally, incubation of human ovarian carcinoma (SKOV3) cells with an NDBF-caged version of a farnesylated peptide followed by UV irradiation resulted in migration of the peptide from the cytosol/Golgi to the plasma membrane due to enzymatic palmitoylation. Overall, the high cleavage efficiency devoid of side reactions and significant two-photon cross-section of NDBF render it superior to Bhc for thiol group caging. This protecting group should be useful for a plethora of applications ranging from the development of light-Activatable cysteine-containing peptides to the development of light-sensitive biomaterials.

One pot synthesis of diarylfurans from aryl esters and PhI(OAc)2 via palladium-associated iodonium ylides

The example of palladium-catalyzed intermolecular cyclization for the synthesis of various diarylfurans in which one of the aromatic rings originates from the phenolic part of the starting ester and the other one from PhI(OAc)2 has been reported. The reaction is carried out through two steps: the rearrangement of palladium-associated iodonium ylides to form o-iodo diaryl ether and then palladium catalyzed intramolecular direct arylation. This reaction can tolerate a variety of functional groups and is alternative or complementary to the previous methods for the synthesis of diarylfurans.

Improved synthesis of a Smad3 phosphorylation inhibitor lingzhifuran A via condensation reaction

A facile and high-efficient synthesis of lingzhifuran A, a Smad3 phosphorylation inhibitor isolated from Ganoderma lucidum, was developed from commercially available dibenzo[b,d]furan. The crucial step of this strategy was achieved via condensation reaction using key intermediate 8-hydroxydibenzo[b,d]furan-4-carbaldehyde and commercially available (E)-2-methylbut-2-enal. By this strategy, lingzhifuran A was obtained in 5 steps with up to 57.6% yield.

Iron-Catalyzed Oxidative C?C Cross-Coupling Reaction of Tertiary Anilines with Hydroxyarenes by Using Air as Sole Oxidant

A mild procedure for the oxidative C?C cross-coupling of tertiary anilines with phenols is described which provides the products generally in high yields and with excellent selectivity. The reaction is catalyzed by the hexadecafluorinated iron–phthalocyanine complex FePcF16 in the presence of substoichiometric amounts of methanesulfonic acid and ambient air as sole oxidant.

Pyrazoles: 'one-pot' synthesis from arenes and carboxylic acids

A rapid and efficient method for 'one-pot' synthesis of pyrazoles from (hetero)arenes and carboxylic acids via successive formation of ketones and β-diketones followed by heterocyclization with hydrazine has been developed. The utility of the RCOOH/TfOH/TFAA acylation system for intermediate production of ketones and 1,3-diketones is a key feature of this approach. The preliminary evaluation of the anticancer activity of the synthesized pyrazoles is performed.

"one-Pot" Synthesis of γ-Pyrones from Aromatic Ketones/Heteroarenes and Carboxylic Acids

Despite the various attractive properties of γ-pyrones, there are still some deficiencies in their synthetic approaches such as lower atom economy, multistep processes, and prefunctionalization of the reagents. In this work, an efficient and simple (CF3CO

Base-Mediated Meerwein-Ponndorf-Verley Reduction of Aromatic and Heterocyclic Ketones

An experimental protocol to achieve the Meerwein-Ponndorf-Verley (MPV) reduction of ketones under mildly basic conditions is reported. The transformation is tolerant of a range of ketone substrates, including O- and S-containing heterocycles, is scalable, and shows potential to be used as a platform to access enantioenriched products. These studies provide a general method for achieving the reduction of ketones under mildly basic conditions and offer an alternative protocol to more well-known Al-based MPV reduction conditions.

Fused imidazole compounds with indoleamine 2,3-dioxygenase inhibition activity

The invention relates to fused imidazole compounds, and a preparation method and application thereof. The structure of the compounds is shown in a general formula I, wherein the definitions of each group are as described in the specification. The compounds are capable of selectively inhibiting indoleamine 2,3-dioxygenase (IDO). The compounds provided by the invention can be used as IDO inhibitorsfor the treatment and/or prevention of diseases with the pathological characteristics of IDO mediated tryptophan metabolism pathways, such as cancer, eye diseases, autoimmune diseases, psychological disorders, depression, anxiety and other diseases.

Visible-Light-Promoted Synthesis of Dibenzofuran Derivatives

Dibenzofurans are naturally occurring molecules that have received considerable attention for a variety of practical applications, such as in pharmaceuticals and electronic materials. Herein, an efficient and eco-friendly method for the synthesis of dibenzofuran derivatives via intramolecular C-O bond formation, which involves the in situ production of a diazonium salt, is described. The transformation requires a diazotizing agent and is promoted by the use of an organic photosensitizer under visible-light irradiation.