2113-51-1

Basic information

• Product Name: 2-Iodobiphenyl
• Synonyms: O-IODODIPHENYL;2-IODOBIPHENYL;2-iodo-1,1’-biphenyl;2-Iodo-1,1'-biphenyl;2-iodo-1’-biphenyl;2-iodo-bipheny;Biphenyl, 2-iodo-;o-Iodobiphenyl
• CAS NO: 2113-51-1
• Molecular Formula: C₁₂H₉I
• Molecular Weight: 280.1
• EINECS: 218-303-3
• Product Categories: Biphenyl derivatives;Aryl;C9 to C12;Halogenated Hydrocarbons
• Mol File: 2113-51-1.mol
• Article Data: 80

Chemical Properties

• Melting Point: 55-57 °C
• Boiling Point: 300 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.59 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000295mmHg at 25°C
• Refractive Index: n20/D 1.662(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 2206820
• CAS DataBase Reference: 2-Iodobiphenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodobiphenyl(2113-51-1)
• EPA Substance Registry System: 2-Iodobiphenyl(2113-51-1)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-63-42/43
• Safety Statements: 26-36-36/37/39-23
• WGK Germany: 3
• RTECS: DV5384800
• TSCA: Yes
• Hazardous Substances Data: 2113-51-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemical Synthesis:
2-Iodobiphenyl is used as an organic chemical synthesis intermediate, playing a crucial role in the formation of various complex organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Iodobiphenyl is used as a key component in the synthesis of dibenziodolium tosylate. This synthesis involves reacting 2-Iodobiphenyl with hydroxy(tosyloxy)iodo] benzene in acetonitrile, which can lead to the development of new pharmaceutical compounds with potential therapeutic applications.

InChI:InChI=1/C12H9I/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H

Upstream product

• 110-86-1 pyridine 
• 591-50-4 iodobenzene 
• 94-36-0 dibenzoyl peroxide 
• 98-95-3 nitrobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 75-05-8 acetonitrile 
• 58109-40-3 diphenyliodonium hexafluorophosphate 
• 7169-58-6 1-(2-iodophenyl)diazonium tetrafluoroborate 
• 98-80-6 phenylboronic acid 
• 75-52-5 nitromethane 
• 60504-04-3 2-dichloroiodanyl-biphenyl 
• 64-19-7 acetic acid 
• 86-00-0 2-nitrobiphenyl 
• 583-55-1 1-Bromo-2-iodobenzene 

Downstream Products

• 6813-30-5 4-biphenyl-2-yl-benzophenone 
• 1165-58-8 o,p-quaterphenyl 
• 6738-04-1 2-phenoxy-1,1'-biphenyl 
• 7104-67-8 2,2'''-diphenyl-p-quaterphenyl 
• 14010-93-6 5-phenyl-5H-dibenzo[d,b]borole 
• 20434-43-9 o-Biphenyl-dimesityl-boran 
• 3598-78-5 5-biphenyl-2-yl-5H-5λ⁵-[5,5']spirobi(benzo[b]phosphindole) 
• 69680-65-5 5-biphenyl-2-yl-3,7-dimethyl-5H-5λ⁵-spiro[benzo[b]arsindole-5,11'-dibenzo[b,g]arsindole] 
• 17040-69-6 Bis--chlorarsin 
• 854243-57-5 2-phenyl-bibenzyl-α-ol 
• 641-96-3 2,2'-diphenylbiphenyl 
• 16291-40-0 1-phenyltriphenylene 
• 4740-52-7 o-sexiphenyl 
• 92-52-4 biphenyl 

Relevant articles and documents

Synthesis and stereochemical studies of di and tetra 9,9′- spirobifluorene porphyrins: New building blocks for catalytic material

We report the synthesis and stereochemical properties of a new class of molecules containing a covalently-linked porphyrin and spiro-9,9′- bifluorene derivatives. The large spiro substituents hinder rotation about the meso position to give atropisomers which can be detected by 1H NMR after phosphine or isocyanide complexation to the ruthenium spiroporphyrins.

Pt(II) metal complexes tailored with a newly designed spiro-arranged tetradentate ligand; Harnessing of charge-transfer phosphorescence and fabrication of sky blue and white OLEDs

Tetradentate bis(pyridyl azolate) chelates are assembled by connecting two bidentate 3-trifluoromethyl-5-(2-pyridyl)azoles at the six position of pyridyl fragment with the tailored spiro-arranged fluorene and/or acridine functionalities. These new chelates were then utilized in synthesizing a series of Pt(II) metal complexes [Pt(Ln)], n = 1-5, from respective chelates L1-L5 and [PtCl2(DMSO)2] in 1,2-dimethoxyethane. The single-crystal X-ray structural analyses were executed on 1, 3, and 5 to reveal the generalized structures and packing arrangement in crystal lattices. Their photophysical properties were measured in both solution and solid state and are discussed in the context of computational analysis. These L1-L5 coordinated Pt(II) species exhibit intense emission, among which complex 5 shows remarkable solvatochromic phosphorescence due to the dominant intraligand charge transfer transition induced by the new bis(pyridyl azolate) chelates. Moreover, because of the higher-lying highest occupied molecular orbital of acridine, complex 5 can be considered as a novel bipolar phosphor. Successful fabrication of blue and white organic light-emitting diodes (OLEDs) using Pt(II) complexes 3 and 5 as the phosphorescent dopants are reported. In particular, blue OLEDs with 5 demonstrated peak efficiencies of 15.3% (36.3 cd/A, 38.0 lm/W), and CIE values of (0.190, 0.342) in a double-emitting layer structure. Furthermore, a red-emitting Os(II) complex and 5 were used to fabricate warm-white OLEDs to achieve peak external quantum efficiency, luminance efficiency, and power efficiency values as high as 12.7%, 22.5 cd/A, and 22.1 lm/W, respectively.

Synthesis of 4-alkylidene-substituted 1,2,3,4-tetrahydroisoquinolines via palladium-catalyzed carbopalladation/C-H activation of 2-bromobenzyl-N-propargylamines

Abstract Tetrasubstituted alkene-based 1,2,3,4-tetrahydroisoquinolines are synthesized via the formation of a cyclic carbopalladation complex followed by C-H bond activation of the sp2 carbon in arenes. This domino reaction proceeds with good selectivity and provides good yields of the products. The requisite starting materials are synthesized by copper(I) iodide catalyzed A3-coupling reactions.

Pd-Catalyzed C(sp3)-H Biarylation via Transient Directing Group Strategy

Here, we describe a highly selective Pd-catalyzed C(sp3)-H biarylation of 2-methylbenzaldehydes using cyclic diaryliodonium salts as arylation reagents. The key strategy is the employment of tert-leucine as a bidentate transient directing group for the proximity-driven metalation to achieve reactivity and selectivity in C-H activation. Various functionalized biaryls bearing both aldehyde and iodine functional groups were prepared successfully, which could be further transformed into a wide range of compounds with potential applications in pharmaceutical chemistry and materials science.

Modular Tandem Mizoroki-Heck/Reductive Heck Reactions to Construct Fluorenes from Cyclic Diaryliodoniums

Starting from cyclic diaryliodoniums and terminal alkenes, a diverse set of fluorenes is conveniently constructed. The reactions catalyzed by palladium undergo one conventional Mizoroki-Heck reaction and one reductive Heck reaction. The scope of alkenes is general, leading to 29 fluorenes which would expand the structural diversity of fluorene reservoir. (Figure presented.).

Palladium-Catalyzed [4 + 3] or [2 + 2 + 3] Annulation via C-H Activation and Subsequent Decarboxylation: Access to Heptagon-Embedded Polycyclic Aromatic Hydrocarbons

The construction of a seven-membered ring in the polycyclic aromatic hydrocarbon skeleton remains a notoriously difficult but attractive challenge. Herein a novel palladium-catalyzed [4 + 3] decarboxylative annulation of 2-iodobiphenyls with 2-(2-halophenyl)acrylic acids is reported, which provides an efficient approach for assembling various tribenzo[7]annulenes via a C-H activation and decarboxylation process. Moreover, tribenzo[7]annulenes can be also synthesized via a [2 + 2 + 3] decarboxylative annulation strategy by employing readily available 1,2-halobenzenes, phenylboronic acids, and 2-(2-halophenyl)acrylic acids.

Scalable electrochemical synthesis of diaryliodonium salts

Cyclic and acyclic diaryliodonium are synthesised by anodic oxidation of iodobiaryls and iodoarene/arene mixtures, respectively, in a simple undivided electrolysis cell in MeCN-HFIP-TfOH without any added electrolyte salts. This atom efficient process does not require chemical oxidants and generates no chemical waste. More than 30 cyclic and acyclic diaryliodonium salts with different substitution patterns were prepared in very good to excellent yields. The reaction was scaled-up to 10 mmol scale giving more than four grams of dibenzo[b,d]iodol-5-ium trifluoromethanesulfonate (>95%) in less than three hours. The solvent mixture of the large-scale experiment was recovered (>97%) and recycled several times without significant reduction in yield.

Iodine-Catalyzed Methylthiolative Annulation of 2-Alkynyl Biaryls with DMSO: A Metal-Free Approach to 9-Sulfenylphenanthrenes

An iodine-catalyzed sustainable, cost-effective, and atom-economic synthetic methodology is developed to synthesize a wide variety of valuable sulfenylphenanthrenes and polycyclic heteroaromatics in moderate to high yield through electrophilic thiolative annulation of 2-alkynyl biaryls (6-endo-dig cyclization) using methyl sulfoxides such as dimethyl sulfoxide (DMSO) as the sulfur source under transition-metal-free conditions. The transformation requires only iodine in a catalytic amount and trifluoroacetic anhydride. Notably, DMSO played multiple roles such as methylthiolating reagent, oxidant, and solvent in this reaction.

α-Bromoacrylic Acids as C1 Insertion Units for Palladium-Catalyzed Decarboxylative Synthesis of Diverse Dibenzofulvenes

Herein α-bromoacrylic acids have been employed as C1 insertion units to achieve the palladium-catalyzed [4 + 1] annulation of 2-iodobiphenyls, which provides an efficient platform for the construction of diverse dibenzofulvenes. This protocol enables the formation of double C(aryl)-C(vinyl) bonds via a C(vinyl)-Br bond cleavage and decarboxylation. It is particularly noteworthy that the method features a broad substrate scope, and various interesting frameworks, such as bridged ring, fused (hetero)aromatic ring, and divinylbenzene, can be successfully incorporated into the products.

Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids

A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.