205-39-0

Usage

Uses

Used in Environmental Monitoring and Research:
Benzo[b]naphtho[1,2-d]furan is utilized as a marker for environmental pollution and health risk assessment due to its association with incomplete combustion processes and its carcinogenic properties. It aids in identifying areas of high pollution and potential health hazards, prompting further investigation and remediation efforts.
Used in Toxicological Studies:
In the field of toxicology, benzo[b]naphtho[1,2-d]furan serves as a subject for research to better understand its toxicological effects and potential health hazards. This includes studying its impact on DNA, the mechanisms of mutation induction, and the long-term effects of exposure on human health.
Used in Occupational Health and Safety:
Benzo[b]naphtho[1,2-d]furan is used as a reference chemical in occupational health and safety protocols to ensure proper handling and disposal methods. This is crucial for minimizing the risk of respiratory and skin irritation among workers exposed to this hazardous substance during processes such as combustion of organic materials.
Used in Regulatory Compliance and Policy Making:
In regulatory agencies and policy-making bodies, benzo[b]naphtho[1,2-d]furan is considered when establishing environmental standards and guidelines. Its identification as a hazardous substance informs the development of regulations aimed at controlling emissions and reducing exposure to this pollutant in various industries.

InChI:InChI=1/C16H10O/c1-2-6-12-11(5-1)9-10-15-16(12)13-7-3-4-8-14(13)17-15/h1-10H

Upstream product

• 855290-64-1 3,4-dihydro-2H-benzo[b]naphtho[1,2-d]furan-1-one 
• 110378-08-0 benzo[b]naphtho[1,2-d]furan-5-carboxylic acid 
• 694-80-4 2-bromo-1-chlorobenzene 
• 15147-55-4 2-naphtholate 
• 583-55-1 1-Bromo-2-iodobenzene 
• 615-42-9 1,2-Diiodobenzene 
• 142095-78-1 1-(2-chlorophenyl)-2-naphthol 
• 142095-77-0 1-(2-bromophenyl)naphthalen-2-ol 
• 142095-76-9 1-(2-iodophenyl)naphthalen-2-ol 
• 159052-03-6 (E)-1-(2-Methoxy-phenyl)-4-phenyl-1-(triphenyl-λ⁵-phosphanylidene)-but-3-en-2-one 
• 66691-27-8 2-(naphthalen-2-yloxy)-benzoic acid 
• 1440730-11-9 2-(naphthalene-2-yloxy)phenyl pivalate 
• 92964-67-5 2-(2-naphthalen-2-yloxy)phenol 
• 479669-16-4 2-(2-naphthoxy)phenyl trifluoromethanesulfonate 

Downstream Products

• 1383607-08-6 6-phenylbenzo[b]naphtho[1,2-d]furan 
• 1382763-43-0 6-[3-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan 
• 1382763-47-4 6-[4-(9,10-diphenyl-2-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan 
• 1382763-49-6 6-[4-(10-phenyl-9-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan 
• 1382763-54-3 (benzo[b]naphtho[1,2-d]furan-6-yl)boronic acid 
• 1382763-45-2 6-[3-(10-phenyl-9-anthryl)phenyl]-benzo[b]naphtho[1,2-d]furan 

Relevant academic research and scientific papers

A chemo- And regioselective Pd(0)-catalyzed three-component spiroannulation

A chemo- and regioselective Pd(0)-catalyzed spiroannulation has been successfully developed. The key feature of this method is the use of readily available 1,2-dihaloarenes, alkynes and 2-naphthols for the rapid assembly of spirocarbocyclic molecules. Mechanistic studies revealed that this domino reaction proceeded through a cascade of oxidative addition to Pd(0), alkyne migratory insertion, and 2-naphthol-facilitated dearomatizing [4+1] spiroannulation.

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

Helicene synthesis by Br?nsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH]

A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C-C bond formation by Suzuki-Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes.

Pd-Catalyzed Denitrative Intramolecular C-H Arylation

A Pd-catalyzed intramolecular C-H arylation of nitroarenes has been developed. Nitroarenes bearing tethered aryl groups at the ortho-position can be readily prepared in one step from 2-halonitroarenes by a nucleophilic aromatic substitution (SNAr). Under Pd/BrettPhos catalysis, activations of the C-NO2 bond as well as the C-H bond on arenes generated the corresponding biaryl linkage in moderate to excellent yields.

Naphthylbenzofuran derivative and preparation method thereof

The invention belongs to the technical field of organic synthesis and particularly relates to a naphthylbenzofuran derivative and a preparation method thereof. The preparation method comprises that a1-bromo-2-naphthol derivative and a phenylboronic acid derivative undergo a reaction to produce an intermediate, the intermediate undergoes an intramolecular dehydration and ring-forming reaction under the action of cesium carbonate to produce the naphthylbenzofuran derivative. The naphthylbenzofuran and its derivative can be used as important synthesis intermediates of functional organic semiconductors such as organic electroluminescence devices, organic solar batteries, organic lasers, optical switches and ion detectors. The modified compound can be used as light-emitting host and guest materials, a carrier transport material and an exciton-blocking material in organic electroluminescent devices. The invention can provide the naphthylbenzofuran derivative with the advantages of simple processes, low synthesis condition requirements, high synthesis yield, industrial large-scale production feasibility and good economic benefits and the preparation method thereof.

Regioselective Synthesis of Polycyclic and Heptagon-embedded Aromatic Compounds through a Versatile π-Extension of Aryl Halides

A versatile π-extension reaction was developed based on the three-component cross-coupling of aryl halides, 2-haloarylcarboxylic acids, and norbornadiene. The transformation is driven by the direction and subsequent decarboxylation of the carboxyl group, while norbornadiene serves as an ortho-C?H activator and ethylene synthon via a retro-Diels–Alder reaction. Comprehensive DFT calculations were performed to account for the catalytic intermediates.

Pd(0)-catalyzed chemoselective construction of spirocarbocycles via an alkyne insertion/β-naphthol dearomatization cascade

A microwave-assisted Pd(0)-catalyzed alkyne migratory insertion/β-naphthol dearomatization cascade process has been accomplished to access a variety of spirocyclic compounds bearing all-carbon quaternary stereogenic centers in high yields with excellent chemoselectivities.

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.

Experimental NMR and DFT studies of persistent carbocations derived from hetero-polycyclic aromatic hydrocarbons containing oxygen atom: Dibenzo[b,d]furan, Benzo[b]naphtho[1,2-d]furan, Benzo[b]naphtho[2,3-d]furan, Benzo[b]naphtho[2,1-d]furan, and Dinaphtho[2,1-b: 1′,2′-d]furan

Persistent protonation carbocations generated from hetero-PAHs containing oxygen atoms in their aromatic rings, dibenzo[b,d]furan (5), benzo[b]naphtho[1,2-d]furan (6), benzo[b]naphtho[2,3-d]furan (7), benzo[b]naphtho[2,1-d]furan (8), and dinaphtho[2,1-b: 1′,2′-d]furan (9), were directly observed by NMR measurements in superacid. Compound 5 was protonated mainly at C(2) in FSO3H-SbF5 (1: 1) or (4: 1)/SO2ClF, and 6, 8, and 9 were protonated exclusively at C(5) in CF3SO3H or FSO3H/SO2ClF, whereas 7 was protonated at C(6) and C(11) to give two species in FSO3H/SO2ClF. Surprisingly, compound 5 resists protonation in FSO3H/SO2ClF to show NMR spectra corresponding to that of the intact material. Positive charge delocalization mapping for carbocations based on experimental Δδ13C values indicates limited delocalization in these systems. The chemical shifts and charge delocalization modes derived by DFT calculations agreed with the experimental results.

Di-tert-butylneopentylphosphine (DTBNpP): An Efficient Ligand in the Palladium-Catalyzed α-Arylation of Ketones

Di-tert-butylneopentylphosphine (DTBNpP) and palladium(II) acetate provide an efficient catalytic system for the α-arylation of ketones. Aryl bromides were coupled with ketones using 0.25-0.5 mol-% Pd(OAc)2/DTBNpP in toluene at 50 C, whereas aryl chlorides required a higher catalyst loading (0.5-2.0 mol-%) and a higher temperature (80 C). Coupling of 2-bromophenol with ketones using the Pd/DTBNpP system provides an efficient route for the synthesis of benzofurans.