615-41-8

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Chloro-2-iodobenzene is used as a reactant for the synthesis of biaryl derivatives of seasamol, which are known for their antioxidant activity against DPPH radicals. This application is particularly relevant in the development of new drugs and pharmaceutical compounds.
2. Used in Chemical Synthesis:
1-Chloro-2-iodobenzene serves as a precursor in the preparation of various organic compounds, such as 2,2'-dichloro-biphenyl, N,N-diaryl-o-phenylenediamines, and 4(5)-(2-chlorophenyl)-1H-imidazole. These compounds have diverse applications in different industries, including pharmaceuticals, materials science, and chemical research.
3. Used in Material Science:
In the field of material science, 1-chloro-2-iodobenzene is involved in the synthesis of novel compounds with potential applications in various areas, such as electronics, coatings, and polymers.
4. Used in Research and Development:
1-Chloro-2-iodobenzene is also utilized in research and development for the exploration of new chemical reactions and the synthesis of innovative organic compounds with potential applications in various industries.
General Description:
1-Chloro-2-iodobenzene is a versatile organic compound that reacts with lanthanum metal in the presence of trimethylchlorosilane to yield 1-chloro-2-trimethylsilylbenzene, further demonstrating its utility in chemical synthesis and research.

InChI:InChI=1/C6H4ClI/c7-5-3-1-2-4-6(5)8/h1-4H

Upstream product

• 95-51-2 o-chloroaniline 
• 1608-42-0 benzenedizolium-2-carboxylate 
• 15842-76-9 (2-chloro-phenyl)-trimethyl-silane 
• 591-50-4 iodobenzene 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 108-90-7 chlorobenzene 
• 108-95-2 phenol 
• 76-05-1 trifluoroacetic acid 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 7553-56-2 iodine 
• 94-36-0 dibenzoyl peroxide 
• 100-44-7 benzyl chloride 
• 10034-85-2 hydrogen iodide 
• 694-80-4 2-bromo-1-chlorobenzene 

Downstream Products

• 2689-07-8 2-chlorodiphenyl ether 
• 19256-46-3 2-deuteriochlorobenzene 
• 13029-08-8 2,2'-Dichlorobiphenyl 
• 39655-09-9 2-iodo-2’-methylbiphenyl 
• 7287-72-1 tris(2-chlorophenyl)amine 
• 779-76-0 2,2'-dichlorodiphenylamine 
• 122899-23-4 2-<(2-chlorophenyl)thio>pyridine 
• 106920-22-3 1,2-bis(pyridin-2-ylthio)benzene 
• 83665-89-8 2-[(Z)-3-(2-Chloro-phenyl)-allyl]-isoindole-1,3-dione 
• 83665-59-2 (E)-2-(3-(2-chlorophenyl)allyl)isoindoline-1,3-dione 
• 89-98-5 2-chloro-benzaldehyde 
• 104014-41-7 1-<2-<(2-Chlorphenyl)amino>phenyl>ethanon 
• 5162-03-8 (2-chlorophenyl)(phenyl)methanone 
• 104581-35-3 1-(2-Chloro-phenylethynyl)-cyclohexanol 

Relevant academic research and scientific papers

Simple preparation of high-quality graphene flakes without oxidation using potassium salts

Preparation of graphene flakes without oxidation is important to preserve the superb intrinsic properties of graphene. A new and simple route to produce few-layer, flake-type graphene with minimized oxidation (2%) by the intercalation of potassium into raw graphite using potassium salts is proposed. Copyright

The graphite-catalyzed: ipso -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes

An efficient, metal-free, and sustainable strategy has been described for the ipso-functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, i.e., phenols, anilines, nitroarenes, and haloarenes, has been prepared via the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed via numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.

Arene diazonium saccharin intermediates: A greener and cost-effective alternative method for the preparation of aryl iodide

In the current protocol, the arene diazonium saccharin derivatives were initially produced from various substituted aromatic amines; subsequently, these intermediates were treated with a greener organic iodide for the preparation of the aryl iodide. We tried to choose low-cost, commercially available, biodegradable, recoverable, ecofriendly, and safe reagents and solvents. The arene diazonium saccharin intermediates could be stored in the liquid phase into a refrigerator for a long time with no significant loss activity. The outstanding merits of the current protocol (a) included the partial recovering of saccharin and tetraethylammonium salt, (b) reduce the use of solvents and the reaction steps due to eliminating separation and purification of intermediates, (c) good yield of the sterically hindered substrates, and (d) avoid the generation of heavy metal or corrosive waste.

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols

We herein report Cu mediated side-directed dehydroxyalkylative halogenation of aryl alcohols. C(aryl)-C bonds of aryl alcohols were effectively cleaved, affording the corresponding aryl chlorides, bromides and iodides in excellent yields. Aryl alcohols could serve as both aromatic electrophilic and radical synthetic equivalents during the reaction.

An efficient gram scale synthesis of aryl iodides from aryl diazofluoroborates in water under mild conditions

Transition metal-free synthesis of synthetically valuable aryl iodides from aryl diazofluroborates in water under mild conditions has been described. Majority of synthesized aryl iodides are obtained in quantitative yields (>99%) under present reaction conditions. The structural effects due to the substituents present on aryl diazofluoroborates did not show any satisfactory effect on the yields of the aryl iodides. Hence, the methodology presented here was found to be adventitious for the quantitative production of synthetically valuable aryl iodides.

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.

A facile and sustainable protocol to the preparation of aryl iodides using stable arenediazonium bis(trifluoromethylsulfonyl)imide salts via the telescopic process

The preparation of aryl iodides in a telescopic reaction using tert-butyl nitrite as a diazotization reagent and a mixture of bis(trifluoromethane) sulfonamide and glacial acetic acid as a mild acidic agent in ethanol followed by iododediazoniation with tetraethylammonium iodide in water was investigated. The current method has other advantages such as minimized waste by avoiding solvent for the purification of products in diazotization step, simple experimental procedure, and good yield of the sterically hindered aryl amines, metal and strong acid-free waste and environmentally benign conditions. The noteworthy features of this study are the preparation of stable arenediazonium bis(trifluoromethylsulfonyl)imide salts that can be used with no significant loss activity after 1?week and bis(trifluoromethane)sulfonamide was recovered in high yields from reactions.

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.

Eco-compatible zeolite-catalysed continuous halogenation of aromatics

A completely eco-compatible halogenation reaction of arenes has been developed allowing high conversions (>95%) of iodobenzene with nearly 100 kg iodobenzene converted per kgcat in one day. Several solid acids, zeolites being the most promising, have been successfully tested in the chlorination reaction of iodobenzene by using trichloroisocyanuric acid (TCCA), a green chlorination agent. H-?BEA zeolites were found to be the most active catalysts for this model halogenation reaction. A strong structure-activity relationship could be established by thorough characterisation (SEM, BET, XRD, FTIR) of various synthetic zeolites. Indeed, nano-sized ?BEA zeolites and more specifically nanosponge-like ?BEA crystals exhibited the highest catalytic performance with a conversion up to 100% and a selectivity toward monochlorinated products up to 98%. Finally, the gained knowledge was applied to set-up an eco-compatible continuous flow halogenation process of different aromatics catalysed by H-?BEA zeolites.

Metal-free iodination of arylboronic acids and the synthesis of biaryl derivatives

A simple, general and efficient method is developed for the metal-free iodination of arylboronic acids. The protocol uses very cheap molecular iodine as the halide source and potassium carbonate as the base. The method is highly tolerant of various functional groups present in the substrates. Importantly, the iodination strategy can also be applied very effectively in the one-pot, two-step synthesis of biaryl derivatives. Georg Thieme Verlag Stuttgart New York.