5943-11-3

Basic information

• Product Name: 2,8-Diiodo-dibenzofuran
• Synonyms: 2,8-Diiodo-dibenzofuran;2,8-diiododibenzo[b,d]furan
• CAS NO: 5943-11-3
• Molecular Formula: C₁₂H₆I₂O
• Molecular Weight: 419.98438
• Mol File: 5943-11-3.mol

Chemical Properties

• Melting Point: 174.0 to 178.0 °C
• Appearance: /
• CAS DataBase Reference: 2,8-Diiodo-dibenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2,8-Diiodo-dibenzofuran(5943-11-3)
• EPA Substance Registry System: 2,8-Diiodo-dibenzofuran(5943-11-3)

Safety Data

• Hazardous Substances Data: 5943-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,8-Diiodo-dibenzofuran serves as a key reagent in the organic synthesis of a range of pharmaceuticals. Its unique structure and electronic properties make it a valuable intermediate in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 2,8-Diiodo-dibenzofuran is utilized as a reagent for the preparation of various agrochemicals. Its role in the synthesis of bioactive compounds helps in the development of pesticides and other agricultural chemicals that are essential for crop protection and yield enhancement.
Used in Dye and Pigment Synthesis:
2,8-Diiodo-dibenzofuran also functions as a precursor in the synthesis of organic dyes and pigments. Its chemical properties allow for the creation of colorants that have specific applications in various industries, such as textiles, plastics, and printing inks, where colorfastness and stability are crucial.
While the provided materials do not detail specific applications or industries beyond the general uses in organic synthesis, pharmaceuticals, agrochemicals, and dye/pigment synthesis, it is clear that 2,8-Diiodo-dibenzofuran plays a significant role in these areas due to its distinctive chemical structure and reactivity. Further research and development could potentially reveal additional applications in other industries where its unique properties can be harnessed.

Upstream product

• 132-64-9 dibenzofuran 

Downstream Products

• 1197989-83-5 2,2'-(dibenzofuran-2,8-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 1240963-92-1 (3-(8-(4-bromophenyl)dibenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole) 
• 1093238-89-1 (3-(8-iodobenzo[b,d]furan-2-yl)-9-phenyl-9H-carbazole) 
• 58841-73-9 2,8-diphenyldibenzofuran 
• 24253-53-0 2,11-diphenyltriphenylene 
• 287957-58-8 2,8-dibenzofuranbis(pentaflurophenyl 3-propionate) 
• 475233-55-7 3-[6-(2-benzyloxycarbonylamino-ethyl)-2,8-bis-trimethylsilanyl-dibenzofuran-4-yl]-propionic acid ethyl ester 
• 475233-56-8 3-[6-(2-benzyloxycarbonylamino-ethyl)-2,8-diiodo-dibenzofuran-4-yl]-propionic acid ethyl ester 

Relevant articles and documents

Carboline modified dibenzofuran as a high triplet host material for blue phosphorescent organic light-emitting diodes

A carboline modified dibenzofuran compound, 2,8-bis(pyrido[2,3-b]indol-9-yl)dibenzofuran (DBFCb), was synthesized and evaluated as the host material for blue phosphorescent organic light-emitting diodes by doping iridium (III) bis((3,5-difluorophenyl)pyridine) picolinate (FIrpic) as a blue triplet emitter. The DBFCb host showed balanced charge density in the emitting layer and a triplet energy of 2.88 eV by carboline moiety. The FIrpic doped DBFCb devices realized high external quantum efficiency of 21.3% at a low doping concentration of 3%.

Alumina-promoted oxodefluorination

A simple protocol for the clean preparation of heterocyclic compounds containing dibenzofuran's core via oxodefluorination of fluoroarenes on activated γ-Al2O3 is reported. Alumina can be considered as a reliable oxygen source enabling one-pot substitution of fluorine atoms and yielding benzoannulated furan derivatives. The corresponding C-F bond activation is selective towards less stable C-Br/C-I and occurs under metal- A nd solvent-free conditions.

Iodine(III)-Mediated, Controlled Di- or Monoiodination of Phenols

An oxidative procedure for the electrophilic iodination of phenols was developed by using iodosylbenzene as a nontoxic iodine(III)-based oxidant and ammonium iodide as a cheap iodine atom source. A totally controlled monoiodination was achieved by buffering the reaction medium with K3PO4. This protocol proceeds with short reaction times, at mild temperatures, in an open flask, and generally with high yields. Gram-scale reactions, as well as the scope of this protocol, were explored with electron-rich and electron-poor phenols as well as heterocycles. Quantum chemistry calculations revealed PhII(OH)·NH3 to be the most plausible iodinating active species as a reactive "I+" synthon. In light of the relevance of the iodoarene moiety, we present herein a practical, efficient, and simple procedure with a broad functional group scope that allows access to the iodoarene core unit.

High triplet energy electron transport type exciton blocking materials for stable blue phosphorescent organic light-emitting diodes

High triplet energy electron transport materials with dibenzothiophene and dibenzofuran cores modified with a diphenyltriazine unit were investigated as electron transport type exciton blocking materials for stable blue phosphorescent organic light-emitting diodes. The two exciton blocking materials showed high triplet energy above 2.80 eV and enhanced quantum efficiency of the blue phosphorescent devices by more than 40% while maintaining stability of the pristine blue devices without the high triplet energy exciton blocking layer.

Molecular design of modifying 4-position of dibenzofuran for high temperature stability and high efficiency

A molecular design modifying 4- position of dibenzofuran with a pyridoindole moiety for high temperature stability and high efficiency was examined as an approach to develop host materials for blue phosphorescent organic light-emitting diodes. The simple pyridoindole modification of 4- position of carbazole substituted dibenzofuran lead to high glass transition temperature above 130°C in addition to high quantum efficiency in the blue phosphorescent device.

NEW DIBENZOFURANS AND DIBENZOTHIOPHENES

The present invention relates to compounds of formula (I) which are characterized in that they are substituted by at least one nitrile substituted carbazolyl group and their use in electronic devices, especially electroluminescent devices. When used as el

AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT

Provided are a long-lifetime organic electroluminescence device which can be fabricated in an improved yield owing to suppressed crystallization of molecules, and an aromatic amine derivative that realizes the device, i.e. , a novel aromatic amine derivative having a specific structure. Specifically provided are an organic electroluminescence device, including an organic thin film layer formed of one or more layers including at least a light emitting layer, the organic thin film layer being interposed between a cathode and an anode, and an aromatic amine derivative for at least one layer of the organic thin film layer, in particular, a hole transporting layer, the derivative having at least one such structure that a substituent in which two or more specific heterocycles are linked to each other, in particular, a substituent in which two or more specific heterocycles are linked through an aryl group is bonded to an amine through an aryl group.

Cyanines as new fluorescent probes for DNA detection and two-photon excited bioimaging

A series of cyanine fluorophores based on fused aromatics as an electron donor for DNA sensing and two-photon bioimaging were synthesized, among which the carbazole-based biscyanine exhibits high sensitivity and efficiency as a fluorescent light-up probe for dsDNA, which shows selective binding toward the AT-rich regions. The synergetic effect of the bischromophoric skeleton gives a several-fold enhancement in a two-photon absorption cross-section as well as a 25- to 100-fold enhancement in two-photon excited fluorescence upon dsDNA binding.

Synthesis of a negatively charged dibenzofuran-based β-turn mimetic and its incorporation into the WW miniprotein-enhanced solubility without a loss of thermodynamic stability

A versatile synthesis has been developed to functionalize the 4-(2-aminoethyl)-6-dibenzofuran propionic acid residue (1a) at the 2 and 8 positions with a variety of different substructures. The unfunctionalized version of this peptidomimetic (1a) is known

2,4,6,8-tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione as a mild and convenient reagent for iodination of aromatic compounds

2,4,6,8-Tetraiodo-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione (tetraiodoglycoluril) is a convenient reagent for preparative iodination of benzene, alkylbenzenes, polycyclic hydrocarbons, aromatic amines, and phenol ethers in organic solvents under mild conditions.