87812-99-5

Usage

Uses

Used in Organic Synthesis:
1-nitrodibenzo[b,d]furan serves as a key intermediate in the synthesis of various organic compounds, playing a crucial role in the creation of a wide array of chemical products.
Used as a Starting Material in Organic Reactions:
In the realm of organic chemistry, 1-nitrodibenzo[b,d]furan is utilized as a starting material for a variety of organic reactions, facilitating the development of new chemical entities and contributing to the advancement of chemical research and innovation.

Upstream product

• 132-64-9 dibenzofuran 
• 99-65-0 meta-dinitrobenzene 
• 533-58-4 2-Iodophenol 
• 104-82-5 4-Methylbenzyl chloride 
• 620-55-3 1-nitro-3-phenoxybenzene 
• 87812-98-4 2',6'-dinitrobiphenyl-2-ol 
• 509-14-8 tetranitromethane 
• 529-28-2 4-iodoanisol 
• 22000-95-9 2-methoxy-2',6'-dinitrobiphenyl 
• 50548-37-3 N-(4-dibenzofuranyl)acetamide 
• 854396-22-8 N-(1-nitro-dibenzofuran-4-yl)-acetamide 
• 629-50-5 Tridecane 
• 1332882-07-1 1-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-1H-imidazole 
• 1332882-06-0 1-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-4,5-dihydro-1H-imidazole 

Downstream Products

• 1332882-07-1 1-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-1H-imidazole 
• 50548-40-8 1-aminodibenzofuran 

Relevant academic research and scientific papers

An aromatic heterocyclic compound and use thereof

The invention provides an aromatic heterocyclic compound. The compound is as shown in formula (1), wherein Y1 is an oxygen atom or a sulfur atom; Y2 is an oxygen atom, a sulfur atom, NR3 or CR1R2, wherein R1, R2 are respectively selected from one of a hydrogen atom, a methyl group, an ethyl group, a propyl group, a tert-butyl group and a phenyl group, and R3 is the hydrogen atom or the phenyl group; X11-X20 are respectively selected from a nitrogen atom or CR4, and at least one of the X11-X20 is a carbon atom which is linked to L1 through a single bond, wherein R4 is the hydrogen atom, a halogen atom or a cyano group; at least one of the X17-X20 is the nitrogen atom. According to the aromatic heterocyclic compound, the aromatic heterocyclic compound has a similar structure as a dibenzofuran derivative and a dibenzothiophene derivative, electron transport can be improved, high light, low voltage, high efficiency and long service life of an organic EL component can be achieved, and the aromatic heterocyclic compound can be extensively applied in an OLED luminescent device and a display device to be used as the host material of a luminescent layer.

Preparation method of 1-iododibenzofuran

The invention provides a preparation method of 1-iododibenzofuran. The preparation method comprises the following steps: adding potassium tert-butoxide, dimethyl ether and cuprous iodide into a firstreactor, stirring the mixture under the protection of nitrogen gas, adding m-dinitrobenzene dissolved with pyridine into a system, then dissolving potassium tert-butoxide and o-iodophenol with dimethyl ether, adding the dissolved mixture into the system, fully reacting under the protection of the nitrogen gas, and separating to obtain 1-nitryldibenzofuran; then adding 1-nitryldibenzofuran into a second reactor, adding ethanol, water, iron powder and ammonium chloride, fully reacting, and separating to obtain 1-aminodibenzofuran; adding the 1-aminodibenzofuran into a third reactor, then addinghydrochloric acid, dropwise adding a sodium nitrite solution and a KI solution, fully reacting, and separating to obtain 1-iododibenzofuran. The preparation method has the beneficial effects of avoidance of carrying out the reactions under an ultralow temperature reaction condition, simple and feasible synthetic method, stable productivity, higher yield and low pollution, and has remarkable advantages on the aspect of batch production.

Tetramethylammonium fluoride tetrahydrate-mediated transition metal-free coupling of aryl iodides with unactivated arenes in air

Biaryls are important compounds with widespread applications in many fields. Tetramethylammonium fluoride tetrahydrate was found to promote the biaryl coupling of aryl iodides bearing electron-withdrawing substituents with unactivated arenes. The reaction takes place at temperatures between 100 and 150°C and can be applied to a wide range of aromatic and heteroaromatic rings, affording the products in moderate to high yields. The reaction does not require strong bases or expensive additives that are employed in the existing methods and can be conducted in air and moisture without any precautions.

PHOSPHORESCENT EMITTERS

Compounds including a ligand with a dibenzo-fused 5-membered ring substituent are provided. In particular, the compounds may be iridium complexes including imidazole coordinated to the dibenzo-substituted ligand. The dibenzo-fused 5-membered ring moiety of the ligand may be twisted or minimally twisted out of plane with respect to the rest of the ligand structure. The compound may be used in organic light emitting devices, particularly as emitting dopants in blue devices. Devices comprising the compounds may demonstrate improved stability while maintaining excellent color.

Photochemical nitration by tetranitromethane part XXX. Product isolation and identification in the photochemical reaction of dibenzofuran

The photolysis of the charge-transfer complex of dibenzofuran (1) and tetranitromethane in either dichloromethane or acetonitrile gives t-2-nitro-r-1-trinitromethyl-1,2-dihydrodibenzofuran (4), the epimeric 4-nitro-1-trinitromethyl-1,4-dihydrodibenzofurans 5 and 7, the epimeric 4-hydroxy-1-trinitromethyl-1,4-dihydrodibenzofurans 6 and 8, 3-trinitromethyldibenzofuran (13), and the four isomeric nitrodibenzofurans 9-12. The five adducts 4-8 are formed via attack by trinitromethanide ion at C1 of the dibenzofuran radical cation, while 3-trinitromethyldibenzofuran is formed by decomposition of an adduct, itself formed via initial attack of trinitromethanide ion at C3 of the dibenzofuran radical cation. The regiochemistry of attack of trinitromethanide ion on the radical cation of the non-alternant dibenzofuran system is in keeping with earlier theoretical predictions. In 1,1,1,3,3,3-hexafluoropropan-2-ol solution the analogous photolysis of the charge-transfer complex of dibenzofuran (1) and tetranitromethane gives only the four nitrodibenzofurans 9-12, the attack of trinitromethanide ion on the radical cation of dibenzofuran being suppressed by the solvent. X-Ray crystal structures are reported for compounds 4, 6 and 13, compound 6 representing the first hydroxytrinitromethyl adduct to be unambiguously assigned this structure. Acta Chemica Scandinavica 1996.

Photochemical Nitration by Tetranitromethane. III. On the Anomalous Nitration and Oxidative Substitution of Dibenzofuran and a Novel Test of the Shaik-Pross Model of Radical Cation Reactivity

The photochemical reaction of dibenzofuran and tetranitromethane in dichloromethane gives predominantly nitro/trinitromethyl adducts and only a small amount of nitro-substitution products.The adducts originate from the reaction between photochemically produced trinitromethanide ion and (dibenzofuran)cation radical, followed by reaction of the trinitromethyl-substituted cyxlohexadienyl radical with NO2.The main sites of attack of trinitromethanide ion are the 1- and the 3-positions.The adducts rapidly eliminate nitroform in the presence of a hindered base.Thus photolysis with with such a base present gives directly a mixture containing predominantly 2- and 4-nitrodibenzofuran.The unexpected attack of trinitromethanide at the 3-position of (dibenzofuran)cation radical is also found in more typical oxidative substitution reactions, such as acetoxylation and cyanation.This isomer distribution is distinctly different from that of electropholic substitution in dibenzofuran (attack at the 2-position), a non-alternant conjugated system.The Shaik-Pross treatment of the radical cation/nucleophile elementary step predicts that the spin density of the corresponding triplet should govern the isomer distribution, and CASSCF calculations show that (dibenzofuran)cation radical then should react predominantly in the 3-position.Thus the electrophilic reactivity of the radical cations of non-alternant systems constitutes a novel test of the configuration mixing model.It is also concluded that the unusual substitution pattern of dibenzofuran with respect to electrophilic nitration is due to incursion of the nitrous acid catalyzed (NAC) reaction.

Positional Reactivity of Dibenzofuran in Electrophilic Substitutions

Isomer distributions of dibenzofuran (DBF) in Friedel-Crafts acylations, Friedel-Crafts alkylations, and nitrations have been determined.The 2- and 3-positions of DBF represents most of the total reactivity.However, the ratio of 2- to 3-isomers greatly varied, depending on the nature of the electrophile.The positional reactivities have been found to be in the following sequence: 2- > 3- > 1- > 4-positions for Friedel-Crafts acylations, Friedel-Crafts benzylations, and nitrations with alkyl nitrate/Lewis acid or nitronium tetrafluoroborate.The ratios for acylations varied over a range from 13.1 to 2.9, while for benzylations and nitrations from 2.0 to 1.0.In contrast, for nitrations of DBF with nitric acid a different reactivity order was found: 3- > 2- > 1- > 4-, with the ratio varying from 0.8 to 0.03 depending on the nature of solvents used.The selectivity for the 3-substitution increased with increase in nitronium ion-like character of nitrating reagents.In particular, nitration with nitric acid in dichloromethane gave mostly 3-nitro-DBF (95percent of the four possible isomeric mixture).The charge-transfer nitration with tetranitromethane under the UV irradiation has shown a similar isomer distribution to that in nitration with nitric acid.The MNDO calculations predicts that the late transition-state model (by ?-complex) favors reactions at the 2-position while the early transition-state model (by HOMO electron density) leads to the 3-substitution.

Copper-Mediated Vicarious Substitution of 1,3-Dinitrobenzene with Iodophenols or Iodomethyl Phenyl Sulfoxide/Sulfone

1,3-Dinitrobenzene reacts with 4-iodophenol or 2-iodophenol in the presence of copper(I) tert-butoxide and pyridine to give 2',6'-dinitrobiphenyl-4-ol and 1-nitrodibenzofuran, respectively, in good yield.Similarly, iodomethyl phenyl sulfone or sulfoxide a

A Remarkable Difference of the Positional Selectivity in Electrophilic Aromatic Substitution of Dibenzofuran between the Classical ?-Complex and Charge-Transfer Mechanisms

Electrophilic nitration of dibenzofuran with nitric acid by a charge-transfer mechanism occurs exclusively at the 3-position and on the other hand, substitution at the 2-position predominates in the acylation, in which a classical ?-complex mechanism is important.