3001-15-8

Basic information

• Product Name: 4,4'-Diiodobiphenyl
• Synonyms: 4-(4'-IODOPHENYL)IODOBENZENE;4,4'-DIIODO-1,1'-BIPHENYL;4,4'-DIIODOBIPHENYL;4,4'-DIIODODIPHENYL;4,4'-DIODOBIPHENYL;1,1'-Biphenyl, 4,4'-diiodo-;4,4’-diiodo-1’-biphenyl;Biphenyl, 4,4'-diiodo
• CAS NO: 3001-15-8
• Molecular Formula: C₁₂H₈I₂
• Molecular Weight: 406.00086
• EINECS: 221-080-5
• Product Categories: Liquid Crystal intermediates;Biphenyl derivatives;pharmacetical;Miscellaneous;Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;White to light yellow crystalline powder;Aryl;C9 to C12;Halogenated Hydrocarbons;Pyridines
• Mol File: 3001-15-8.mol

Chemical Properties

• Melting Point: 201-204 °C(lit.)
• Boiling Point: 380.9 °C at 760 mmHg
• Flash Point: 191.5 °C
• Appearance: Pale yellow to beige/Powder
• Density: 2.041 g/cm³
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in hot Toluene(very faint turbidity).
• Sensitive: Light Sensitive
• CAS DataBase Reference: 4,4'-Diiodobiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Diiodobiphenyl(3001-15-8)
• EPA Substance Registry System: 4,4'-Diiodobiphenyl(3001-15-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-37/38-36-36/37/38
• Safety Statements: 36-37-26
• RIDADR: UN 3152 9/PG 2
• WGK Germany: 3
• TSCA: T
• HazardClass: 9
• PackingGroup: II
• Hazardous Substances Data: 3001-15-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
4,4'-Diiodobiphenyl is used as a chemical intermediate for the synthesis of various organic compounds. Its reactivity and structural features make it a valuable building block in the creation of complex molecules.
Used in the Suzuki Reaction:
In the field of organic chemistry, 4,4'-Diiodobiphenyl is utilized as a reactant in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds.
Used in the Sonogashira-Hagihara Reaction:
4,4'-Diiodobiphenyl is also used as a starting material in the Sonogashira-Hagihara reaction, a cross-coupling reaction that involves the formation of carbon-carbon bonds. In this context, it was coupled with (trimethylsilyl) acetylene to produce the (trimethylsilyl)ethynyl derivative.
Used in Gene Expression Studies:
4,4'-Diiodobiphenyl has been found to enhance the expression of the luciferase gene, making it a useful tool in molecular biology and gene expression research.
Used in the Production of Liquid Crystals:
As an intermediate, 4,4'-Diiodobiphenyl plays a crucial role in the synthesis of liquid crystals, which are widely used in display technologies and other applications that require the manipulation of light and color.

Upstream product

• 92-52-4 biphenyl 
• 5584-41-8 4,4'-bis-phenyliodonio-biphenyl; diiodide 
• 861533-43-9 4,4'-diiodyl-biphenyl 
• 64-19-7 acetic acid 
• 92-87-5 p,p'-diaminobiphenyl 
• 1591-31-7 4-iodo-biphenyl 
• 624-38-4 para-diiodobenzene 
• 7664-93-9 sulfuric acid 
• 7553-56-2 iodine 
• 7697-37-2 nitric acid 
• 76591-15-6 4,4’-bis(diacetoxyiodo)biphenyl 
• 1227476-15-4 Azobenzene 
• 5122-99-6 4-iodophenylboronic acid 
• 1514-50-7 4-iodobenzenediazonium tetrafluoroborate 

Downstream Products

• 135-70-6 p-quaterphenyl 
• 4499-83-6 para-hexaphenyl 
• 76185-65-4 N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl 
• 164724-35-0 N,N,N',N'-tetra[(1,1'-biphenyl)-4-yl]-(1,1'-biphenyl)-4,4'-diamine 
• 619-58-9 4-iodobenzoic acid 
• 1591-31-7 4-iodo-biphenyl 
• 15546-43-7 N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl 
• 27164-41-6 N,N′-dimethyl-N,N′-diphenylbenzidine 
• 22001-04-3 2.2'''.6.6'''-Tetranitro-p-quaterphenyl 
• 7104-67-8 2,2'''-diphenyl-p-quaterphenyl 
• 4969-04-4 3,3'''-diphenyl-p-quaterphenyl 
• 51119-62-1 C₃₈H₄₄N₂O₆S₂ 
• 4061-32-9 4,4'-bis(2-phenylethenyl)bipheny 
• 1486-01-7 biphenyl-d10 

Relevant articles and documents

Conveniently Synthesized Butterfly-Shaped Bitriphenylenes and their Application in Solution-Processed Organic Field-Effect Transistor Devices

Various π-extended new bitriphenylene derivatives (both conformationally-free and conformation-locked) have been successfully synthesized by a facile Scholl oxidative cyclodehydrogenation method in good to excellent yields. Their optical properties in solution and film states reveal possibility for self-ordering. The molecular packing in solid-state demonstrates favorable π–π stacking as well as weak intermolecular interactions leading to face-to-face or slipped-stack arrangements. Besides, these butterfly-shaped large bitriphenylenes display near-UV absorption, excellent photochemical, thermal, and electrochemical stabilities. The all-organic anneal-free transparent FETs fabricated from solution-processable bitriphenylenes showcase significant improvement (ca. 4 orders of magnitude higher) in charge transporting abilities (μh: from ca. 10–7 to 10–3 cm2/(Vs)) when compared to model triphenylene. The fabricated FETs unveil excellent air stability (> 1 year under atmospheric conditions) highlighting the utility of these novel link-locked triphenylene skeletons in organic electronics.

Synthesis, characterization, and systematic structure–property investigation of a series of carbazole–thiophene derivatives

A series of carbazole–thiophene oligomers linked at the 3,6-positions of the carbazole fragment of 4,4′-bis(carbazol-9-yl)biphenyl (CBP) and 4,4′-bis(carbazol-9-yl)-2,2′-dimethylbiphenyl (CDBP) with systematically elongated molecular lengths were synthesized via the Suzuki–Miyaura and Ullmann coupling reactions. Their electronic properties were studied by UV-Vis, cyclic voltammetry, and theoretical calculations. The coupling of CBP and CDBP with thiophene and bi- and terthiophene residues stabilized the HOMO and LUMO energy levels. The absorption and emission spectra exhibited a gradual red shift. The compounds with oligothiophene units had greatly decreased band gaps compared with CBP and CDBP. Therefore, these units may be introduced into the backbone of π-conjugated small molecules to develop new materials with low band gaps that may have potential applications in optoelectronics.

Modular Approach to Kekulé Diradicaloids Derived from Cyclic (Alkyl)(amino)carbenes

A modular approach for the synthesis of Kekulé diradicaloids is reported. The key step is the insertion of a carbene, namely, a cyclic (alkyl)(amino)carbene (CAAC), into the C-H bonds of two terminal alkynes linked by a spacer. Subsequent hydride abstraction, followed by two-electron reduction of the corresponding bis(iminium) salts, affords the desired diradicaloids. This synthetic route readily allows for the installation of communicating spacers, featuring different degrees of aromaticity and lengths, and gives the possibility of generating unsymmetrical compounds with two different CAACs. Electron paramagnetic resonance (EPR), NMR, UV-vis, and X-ray studies in combination with quantum-chemical calculations give insight into the electronic nature of the deeply colored Kekulé diradicaloids. They feature a singlet ground state with varying degrees of diradical character in combination with small singlet/triplet gaps. Upon lengthening of the spacer, the properties of the compounds approach those of monoradicals in which steric protection of the propargyl radical moiety is necessary to inhibit decomposition pathways. Most of these diradicaloids are stable at room temperature, both in solution and in the solid state, but are highly oxygen-sensitive. They represent the first diradicaloids derived from iminium salts.

Silk?Fibroin-Supported Palladium Catalyst for Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides

Recently, we have reported the preparation of a silk fibroin-supported Palladium catalyst (Pd/SF) and its use in the Suzuki-Miyaura cross-coupling of aryl iodides. Since its synthetic applicability and structural features are still far from being fully ex

Visible Light Induced Aerobic Coupling of Arylboronic Acids Promoted by Hydrazone

A visible-light-induced oxidative coupling of arylboronic acids has been developed for the synthesis of biaryls. The reaction that employs polydentate hydrazones as the bifunctional catalyst works smoothly under room temperature. It is compatible with a w

"benchtop" Biaryl Coupling Using Pd/Cu Cocatalysis: Application to the Synthesis of Conjugated Polymers

Typically, Suzuki couplings used in polymerizations are performed at raised temperatures in inert atmospheres. As a result, the synthesis of aromatic materials that utilize this chemistry often demands expensive and specialized equipment on an industrial scale. Herein, we describe a bimetallic methodology that exploits the distinct reactivities of palladium and copper to perform high yielding aryl-aryl dimerizations and polymerizations that can be performed on a benchtop under ambient conditions. These couplings are facile and can be performed by simple mixing in the open vessel. To demonstrate the utility of this method in the context of polymer synthesis: polyfluorene, polycarbazole, polysilafluorene, and poly(6,12-dihydro-dithienoindacenodithiophene) were created at ambient temperature and open to air.

Synergistic Activities in the Ullmann Coupling of Chloroarenes at Ambient Temperature by Pd-Supported Calcined Ferrocenated La2O3

Novel palladium-doped nanoparticles have been explored to serve as the first metal oxide-derived heterogeneous catalyst for Ullmann reaction of chloroarenes under mild condition (34?°C). This heterogeneous catalyst exhibited high catalytic activity towards the Ullmann homocoupling of chloroarenes into a series of useful symmetrically biaryl products with good to excellent yields in the presence of ethanol and NaOH, thereby leading to green and economical Ullmann reaction. The produced nanoparticles were successfully characterized by various techniques including PXRD, XPS, HRTEM, SEM-EDS, BET, TGA techniques, elemental mapping analysis and ICP-OES. Interestingly, based on characterization and experimental data, a reasonable mechanism has been proposed. Also, the formation of aryl methyl ketone as a by-product has been further confirmed by isotopic labelling experiments that the acetyl moiety is derived from ethanol. Moreover, the catalyst was stable and could be easily reused up to 5 times under atmospheric air without suffering significant loss in catalytic activity.

Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids

A rapid, ligand-free, base-accelerated, copper-catalyzed homocoupling reaction of (het)arylboronic acids is presented. A -CuCl2·2H2O/Na2CO3-based catalyst enabled the formation of bi(het)aryl compounds by a homocoupling process in moderate to excellent yields (72-97%) within 15 minutes. A mechanism for the copper-catalyzed base-accelerated reaction is proposed.

Palladium-catalyzed reductive homocoupling of aryl sulfonates via cleavage of C─O bond at room temperature

Palladium-catalyzed reductive homocoupling of aryl sulfonates has been successfully achieved under mild conditions. This transformation is a new method for the homocoupling reaction of aryl sulfonates at room temperature via the cleavage of C─O bonds, thus providing an alternative synthesis of symmetric biaryls. The reported reductive homocoupling reaction is tolerant of many common functional groups regardless of electron-donating or electron-withdrawing nature, making this newly developed transformation important for complementing Ullmann coupling. Experimental Section. Typical procedure for the products.