348-52-7

Usage

Uses

Used in Pharmaceutical Industry:
1-Fluoro-2-iodobenzene is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical properties make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Chemical Synthesis:
1-Fluoro-2-iodobenzene is used as a starting material for the synthesis of various organic compounds, including bridged biphenyl compounds, 1-fluoro-8-methylbiphenylene, and 4-fluoro-5-methylfluorene. These compounds have potential applications in various industries, such as materials science and electronics.
Used in Suzuki Reaction:
1-Fluoro-2-iodobenzene is utilized in the Suzuki reaction, a widely used cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds, which are essential for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and advanced materials.
Used in Synthesis of Chiral O-Phosphanophenyl Sulfoxides:
1-Fluoro-2-iodobenzene is also used in the synthesis of chiral o-phosphanophenyl sulfoxides, which are important intermediates in the preparation of various biologically active compounds and pharmaceuticals. These chiral compounds play a crucial role in the development of enantiomerically pure drugs with improved efficacy and reduced side effects.

Synthesis Reference(s)

Synthetic Communications, 20, p. 1701, 1990 DOI: 10.1080/00397919008053092

Upstream product

• 348-54-9 2-Fluoroaniline 
• 462-06-6 fluorobenzene 
• 131049-54-2 o-potassiofluorobenzene 
• 108-95-2 phenol 
• 7647-01-0 hydrogenchloride 
• 56-23-5 tetrachloromethane 
• 7790-99-0 Iodine monochloride 
• 1072-85-1 o-fluorobromobenzene 
• 128254-27-3 2-Fluoro-1,4-bis-trimethylsilanyl-benzene 
• 1034926-54-9 bis(2-fluorophenyl)iodonium tetrafluoroborate 
• 2926-29-6 Langlois reagent 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 1842-26-8 (2-fluorophenyl)trimethylsilane 
• 445-29-4 o-fluoro-benzoic acid 

Downstream Products

• 388-82-9 2,2'-difluorobiphenyl 
• 55258-70-3 C₁₄H₁₃FO 
• 55258-68-9 2'-fluoro-4-isopropyldiphenyl ether 
• 6933-30-8 (2-fluorophenyl)-(thiophen-2-yl)methanone 
• 36029-96-6 2-fluoro-β,β-difluoro-α-(trifluoromethyl)styrene 
• 130247-07-3 1-<2-(benzyloxycarbonyl)-2-<(tert-butoxycarbonyl)amino>ethenyl>-2-fluorobenzene 
• 141939-68-6 (R)-1-Benzyloxy-4-(2-fluoro-phenyl)-but-3-yn-2-ol 
• 146140-96-7 2,2-dimethyl-N-(4-(2-fluorophenyl)-3-pyridyl)propanamide 
• 148715-48-4 3-<(E)-<2-(2-fluorophenyl)ethenyl>>-4,5-diphenyl-2(3H)oxazolone 
• 462-06-6 fluorobenzene 
• 73828-03-2 o-fluorophenyliodine difluoride 
• 3794-15-8 1-benzyl-2-fluorobenzene 
• 342-24-5 o-fluorobenzophenone 
• 445-27-2 2'-Fluoroacetophenone 

Relevant academic research and scientific papers

Selective C-H Iodination of (Hetero)arenes

Iodoarenes are versatile intermediates and common synthetic targets in organic synthesis. Here, we present a strategy for selective C-H iodination of (hetero)arenes with a broad functional group tolerance. We demonstrate the utility and differentiation to other iodination methods of supposed sulfonyl hypoiodites for a set of carboarenes and heteroarenes.

Synthesis of biaryl compounds via Suzuki homocoupling reactions catalyzed by metal organic frameworks encapsulated with palladium nanoparticles

Heterogeneous homocoupling reactions of phenylboronic acids were greatly accelerated via Suzuki homocoupling reactions. In this work, a tandem route was designed which firstly one part of phenylboronic acids reacted with iodine to form iodobenzenes, then another part of phenylboronic acids coupled with iodobenzenes to produce biaryl compounds. The tandem reaction were catalyzed by a bifunctional heterogeneous catalyst of metal organic frameworks encapsulated with palladium nanoparticles (Pd?MOFs). This strategy for forming symmetric C-C bond between benzene rings has obvious advantages such as high efficiency, easy separation, good recyclability and no addition of toxic halogenated benzene.

Functional Group Transposition: A Palladium-Catalyzed Metathesis of Ar-X σ-Bonds and Acid Chloride Synthesis

We describe the development of a new method to use palladium catalysis to form functionalized aromatics: via the metathesis of covalent σ-bonds between Ar-X fragments. This transformation demonstrates the dynamic nature of palladium-based oxidative addition/reductive elimination and offers a straightforward approach to incorporate reactive functional groups into aryl halides through exchange reactions. The reaction has been exploited to assemble acid chlorides without the use of high energy halogenating or toxic reagents and, instead, via the metathesis of aryl iodides with other acid chlorides.

Utilising Sodium-Mediated Ferration for Regioselective Functionalisation of Fluoroarenes via C?H and C?F Bond Activations

Pairing iron bis(amide) Fe(HMDS)2 with Na(HMDS) to form new sodium ferrate base [(dioxane)0.5?NaFe(HMDS)3] (1) enables regioselective mono and di-ferration (via direct Fe?H exchange) of a wide range of fluoroaromatic substrates under mild reaction conditions. Trapping of several ferrated intermediates has provided key insight into how synchronised Na/Fe cooperation operates in these transformations. Furthermore, using excess 1 at 80 °C switches on a remarkable cascade process inducing the collective twofold C?H/threefold C?F bond activations, where each C?H bond is transformed to a C?Fe bond whereas each C?F bond is transformed into a C?N bond.

Application of trivalent iodine compounds as catalysts in Bal-Schiemann reaction

The invention discloses an application of trivalent iodine compounds shown in formula I and/or II in the description and used as catalysts in Bal-Schiemann reaction. The trivalent iodine compounds areused as the catalysts in the Bal-Schiemann reaction, so that the Bal-Schiemann reaction can be conducted at room temperature or near room temperature when a thermochemical method is used, and the reaction has mild reaction conditions, wide substrate use range and short reaction time, and is safe and easy to operate, products are easy to separate, and raw materials are simple and low in toxicity.

Hypervalent Iodine(III)-Catalyzed Balz–Schiemann Fluorination under Mild Conditions

An unprecedented hypervalent iodine(III) catalyzed Balz–Schiemann reaction is described. In the presence of a hypervalent iodine compound, the fluorination reaction proceeds under mild conditions (25–60 °C), and features a wide substrate scope and good functional-group compatibility.

Expanding the Balz–Schiemann Reaction: Organotrifluoroborates Serve as Competent Sources of Fluoride Ion for Fluoro-Dediazoniation

The Balz–Schiemann reaction endures as a method for the preparation of (hetero)aryl fluorides yet is eschewed due to the need for harsh conditions or high temperatures along with the need to isolate potentially explosive diazonium salts. In a departure from these conditions, we show that various organotrifluoroborates (RBF3?s) may serve as fluoride ion sources for solution-phase fluoro-dediazoniation in organic solvents under mild conditions. This methodology was successfully extended to a one-pot process obviating aryl diazonium salt isolation. Sterically hindered (hetero)anilines are fluorinated under unprecedentedly mild conditions in good-to-excellent yields. Taken together, this work expands the repertoire of RBF3?s to act as fluorine ion sources in an update to the classic Balz–Schiemann reaction.

Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids

A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.

Electrochemical Synthesis of Aryl Iodides by Anodic Iododesilylation

An electrochemical access to iodinated aromatic compounds starting from trimethylsilyl-substituted arenes is presented. By design of experiments, highly efficient and mild conditions were identified for a wide range of substrates. A functional group stability test and the synthesis of an important 3-iodobenzylguanidine radiotracer illustrate the scope of this process.

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.