243-42-5

Basic information

• Product Name: BENZO[B]NAPHTHO[2,3-D]FURAN
• Synonyms: BENZO[B]NAPHTHO[2,3-D]FURAN;BETA-BRAZANE;Benzonaphthofuran;Naphtho[2,3-b][1]benzofuran;b-Brazan.;BENZO[b]NAPHTHO[2,3-d]FURA;BENZO[B]NAPHTHO[2,3-D]FURAN, TECH., 90%;Benzo[b]naphtho[2,3-d]furan,90%,tech.
• CAS NO: 243-42-5
• Molecular Formula: C₁₆H₁₀O
• Molecular Weight: 218.25
• EINECS: 205-955-9
• Product Categories: Furan&Benzofuran
• Mol File: 243-42-5.mol

Chemical Properties

• Melting Point: 202-207 °C
• Boiling Point: 318.94°C (rough estimate)
• Flash Point: 208.3 °C
• Appearance: white to light yellow crystal powder
• Density: 1.0826 (rough estimate)
• Vapor Pressure: 4.62E-06mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• CAS DataBase Reference: BENZO[B]NAPHTHO[2,3-D]FURAN(CAS DataBase Reference)
• NIST Chemistry Reference: BENZO[B]NAPHTHO[2,3-D]FURAN(243-42-5)
• EPA Substance Registry System: BENZO[B]NAPHTHO[2,3-D]FURAN(243-42-5)

Safety Data

• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 36/37
• Hazardous Substances Data: 243-42-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

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

Upstream product

• 855290-66-3 7,8,9,10-Tetrahydro-benzo[b]naphtho[2,3-d]furan 
• 875254-28-7 3-benzylbenzofuran-2-carbaldehyde 
• 479-11-8 benzo[b]naphtho[2,3-d]furan-6,11-dione 
• 101277-90-1 1-(2′-hydroxyphenyl)naphthalene 
• 135-19-3 β-naphthol 
• 2471-91-2 1,3-dihydrobenzo[c]thiophene-2,2-dioxide 
• 66691-27-8 2-(naphthalen-2-yloxy)-benzoic acid 
• 37803-24-0 o-Diacetoxymethyl-benzylbromid 
• 31675-37-3 2-diacetoxymethyltoluene 
• 529-20-4 2-methylphenyl aldehyde 
• 1400883-62-6 C₂₃H₁₈O₄S 
• 1440730-11-9 2-(naphthalene-2-yloxy)phenyl pivalate 
• 19420-29-2 2-phenoxynaphthalene 
• 479669-16-4 2-(2-naphthoxy)phenyl trifluoromethanesulfonate 

Downstream Products

• 243-46-9 benzo[b]naphtho[2,3-d]thiophene 
• 876506-31-9 3-(2-hydroxyphenyl)naphthalen-2-ol 
• 479-11-8 benzo[b]naphtho[2,3-d]furan-6,11-dione 

Relevant articles and documents

A Convenient Route to Heteronaphthacenes

Heteronaphthacenes 1 were prepared in two steps from 1,3-dihydrobenzo[c]thiophene 2,2-dioxide (4) and dienophiles 2 via convenient high-temperature Diels-Alder reactions.

Facile Construction of Furanoacenes by a Three-Step Sequence Going through Disilyl-exo-cyclic Dienes

Facile synthesis of various benzonaphthofurans was achieved by intramolecular hydroarylation of 1,4-disilyl-2-aryloxy-1,3-enynes followed by cycloaddition with arynes or alkenes and finally desilylaromatization. The three-step transformation can be operated sequentially in one-pot, providing with a range of furanoacenes easily and highly effectively.

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.

Microwave-Promoted Pd-Catalyzed Synthesis of Dibenzofurans from Ortho-Arylphenols

ortho-Aryl phenols, synthesized via protecting group free Suzuki–Miyaura coupling of ortho-halophenols and arene boronic acids, undergo a cyclization to dibenzofurans via oxidative C–H activation. The reaction proceeds under microwave irradiation in short reaction times using catalytic amounts of Pd(OAc)2 without additional ligands.

Synthesis of fused dibenzofuran derivatives via palladium-catalyzed domino C-C bond formation and iron-catalyzed cycloisomerization/aromatization

A range of tetracyclic dibenzofuran derivatives bearing a variety of functional groups was readily synthesized via a two-stage domino strategy starting from propargyl ethers of 2-halo phenol derivatives. The first stage in the strategy involves Pd(0)-catalyzed domino intramolecular carbopalladation/Suzuki coupling via 5-exo-dig cyclization onto the alkyne, leading to 3-methylene-2,3-dihydrobenzofuran derivatives. In the second stage of the domino strategy, an iron(III)-catalyzed cycloisomerization and aromatization reaction produces tetracyclic benzofuran derivatives. This two-step sequence provides efficient access to diversely substituted polycyclic dibenzofuran derivatives in high yields and in an atom-efficient and environmentally friendly manner. Moreover, this strategy was also successfully used for the synthesis of a naturally occurring tetracyclic dibenzofuran, β-brazan.

OXYGEN-CONTAINING FUSED RING AMINE COMPOUND, SULPHUR-CONTAINING FUSED RING AMINE COMPOUND, AND ORGANIC ELECTROLUMINESCENT ELEMENT

A fused amine compound including a furan ring or a thiophene ring and an organic electroluminescence device employing the amine compound. The organic electroluminescence device includes a cathode, an anode, and one or more organic thin film layers which are disposed between the cathode and the anode. The organic thin film layers include a light emitting layer and at least one layer of the organic thin film layers includes at least one amine compound.

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.

Lewis acid/Broensted acid mediated benz-annulation of thiophenes and electron-rich arenes

A facile preparation of benz-annulated heterocycles were achieved at rt involving a Lewis acid/Broensted acid mediated annulation of heterocycles using 2,5-dimethoxytetrahydrofuran as a four-carbon synthon. The benz-/naphth-annulation was found to be successful with electron-rich arenes as well.

Rhodium-catalyzed decarbonylative C-H arylation of 2-aryloxybenzoic acids leading to dibenzofuran derivatives

Rhodium-catalyzed intramolecular C-H arylation of 2-aryloxybenzoic acids proceeded accompanied by decarbonylation to give dibenzofuran derivatives in high yields. The present reaction is widely applicable to substrates bearing various functionalities.

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