645-00-1

Usage

Uses

Used in Organic Synthesis:
1-Iodo-3-nitrobenzene is used as a key intermediate in the synthesis of various organic compounds, such as 5-substituted pyrrolo[3,2-b]pyridine amide and 3′-nitro-4-methylthiobiphenyl. Its unique structure allows for versatile reactions and the formation of diverse chemical products.
Used in Palladium(0) Catalyzed Cross-Coupling Reactions:
1-Iodo-3-nitrobenzene is utilized as a reactant in palladium(0) catalyzed cross-coupling reactions between heteroarylzinc iodide and unsaturated iodide. This application is significant in the field of organic chemistry, as it enables the formation of new carbon-carbon and carbon-heteroatom bonds, leading to the creation of complex molecular structures with potential applications in pharmaceuticals, materials science, and other industries.

Upstream product

• 591-50-4 iodobenzene 
• 75-52-5 nitromethane 
• 591-09-3 nitro acetate 
• 20691-72-9 4-iodo-2-nitroaniline 
• 69180-54-7 1-iodosyl-3-nitro-benzene 
• 98-95-3 nitrobenzene 
• 99-09-2 3-nitro-aniline 
• 20942-49-8 C₁₀H₁₄N₄O₂ 
• 141-52-6 sodium ethanolate 
• 73377-26-1 p-Tolyl-m-nitrophenyliodonium Fluoroborate 
• 139-02-6 sodium phenoxide 
• 23351-89-5 m-nitrodiphenyliodonium bromide 
• 16307-37-2 3-nitro(diacetoxyiodo)benzene 
• 50-81-7 ascorbic acid 

Downstream Products

• 16307-37-2 3-nitro(diacetoxyiodo)benzene 
• 16825-78-8 1-iodoxy-3-nitrobenzene 
• 51264-60-9 3-nitro-2'-methylbiphenyl 
• 23377-21-1 1,2-bis(3-iodophenyl)diazene 
• 958-96-3 3,3'-dinitro-1,1'-biphenyl 
• 952-04-5 3-chloro-3'-nitro-biphenyl 
• 620-55-3 1-nitro-3-phenoxybenzene 
• 88-67-5 2-Iodobenzoic acid 
• 50829-58-8 3-(4-methylphenoxy)nitrobenzene 
• 107622-63-9 1-methoxy-2-(3-nitro-phenoxy)-benzene 
• 116530-27-9 (3-nitro-phenyl)-o-tolyl ether 
• 10304-72-0 3-nitro(dichloroiodo)benzene 
• 51294-43-0 4-iodo-1,2-dinitro-benzene 
• 626-01-7 3-Iodoaniline 

Relevant academic research and scientific papers

Synthesis of 4-substituted azopyridine-functionalized Ni(II)-porphyrins as molecular spin switches

We present the synthesis and the spin switching efficiencies of Ni(II)-porphyrins substituted with azopyridines as covalently attached photoswitchable ligands. The molecules are designed in such a way that the azopyridines coordinate to the Ni ion if the azo unit is in cis configuration. For steric reasons no intramolecular coordination is possible if the azopyridine unit adopts the trans configuration. Photoisomerization of the azo unit between cis and trans is achieved upon irradiation with 505 nm (trans→cis) and 435 nm (cis→trans). Concurrently with the isomerization and coordination/decoordination, the spin state of the Ni ion switches between singlet (low-spin) and triplet (high-spin). Previous studies have shown that the spin switching efficiency is strongly dependent on the solvent and on the substituent at the 4-position of the pyridine unit. We now introduced thiol, disulfide, thioethers, nitrile and carboxylic acid groups and investigated their spin switching efficiency.

Low-temperature and highly efficient liquid-phase catalytic nitration of chlorobenzene with NO2: Remarkably improving the para-selectivity in O2-Ac2O-Hβ composite system

In this work, we developed a low-temperature and efficient approach for the highly selective preparation of valuable p-nitrochlorobenzene from the liquid-phase catalytic nitration of chlorobenzene with NO2 in O2-Ac2O-Hβ composite system. The results demonstrated that the introduction of molecular oxygen remarkably enhanced the chlorobenzene conversion and the cooperation catalysis of Hβ zeolite and Ac2O envidently improved the selectivity to para-nitro product. Under the optimized reaction conditions, 93.6 % of the selectivity to p-nitrochlorobenzene with 84.0 % of chlorobenzene conversion was obtained, and the ratio of p-nitrochlorobenzene to o-nitrochlorobenzene could reach up to 20.3. Furthermore, the selectivity distribution of nitration products was reasonably explained by the density functional theory (DFT) calculation. Finally, the possible nitration reaction pathway of chlorobenzene with NO2 was suggested in O2-Ac2O-Hβ composite catalytic system. The present work affords a new and mild nitration approach for highly selective preparation of valuable para-nitro products, and has potential industrial application prospects.

ipso-Bromination/iodination of arylboronic acids: Poly(4-vinylpyridine)-Br2/I2 complexes as safe and efficient reagents

Poly(4-vinyl pyridine) supported bromine/iodine complexes were prepared and probed for ipso-bromination/iodination of arylboronic acids. These solid complexes with catalytic amount of additive are found to be safe and efficient reagent system for the ipso-bromination/iodination. The reaction occurs under mild conditions and tolerates various functional groups resulting in products with high selectivity and yields.

Pd-Catalyzed Decarboxylative Ortho-Halogenation of Aryl Carboxylic Acids with Sodium Halide NaX Using Carboxyl as a Traceless Directing Group

A highly regioselective Pd-catalyzed carboxyl directed decarboxylative ortho-C-H halogenation of cheap o-nitrobenzoic acids with NaX (X = I, Br) under aerobic conditions has been established. The utility of the method has been demonstrated by the gram-scale reaction and derivatization of the product. Experimental results have confirmed Pd and Bi played critical roles in the transformation and indicated the transformation might proceed via 2-halo-6-nitrobenzoic acid derivative intermediate.

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides

Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.

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.

Compound having dual effects on 5-HT and application thereof in treatment of depression

The invention discloses a compound having dual effects on 5-HT and application thereof in treatment of depression. As shown in the description, R1, R2, R3 and R4 are independently selected from H, F or CH3. In recent years, a dual-effect anti-depression drug with partial excitation of serotonin 1A receptor and selective serotonin reuptake inhibition becomes a hot spot for new antidepressant research. In rat synaptosome, [3H]5-HT uptake inhibition and h5-HT1A binding affinity experiments prove that the compound has 5-HT reuptake inhibition effect and 5-HT1A receptor excitation effect, indicating that the compound can be used as a medicament for treating central nervous system dysfunction such as depression and anxiety in humans.

Compound having dual functions to 5-HT and application thereof in depressive disorder treatment

The invention discloses a compound having dual functions to 5-HT and application thereof in depressive disorder treatment. The formula is shown in the description, wherein R1, R2, R3 and R4 are independently selected from H, F or OH. In recent years, an antidepressant having the dual functions of 5-hydroxytryptamine 1A acceptor partial agitation and selective 5-hydroxytryptamine re-uptake inhibition becomes a hot point direction of a novel antidepressant drug research. In a [3H]5-HT uptake inhibiting effect experiment of a rat synaptosome and a h5-HT1A combined affinity experiment, the compound is verified to have the 5-HT re-uptake inhibiting effect and the agitating effect to a 5-HT1A acceptor. The fact that the compound can be used as a drug for treating human central nervous system disorders, such as a depressive disorder and an anxiety disorder, is demonstrated.

Drug for treating depression

The invention discloses a drug for treating depression. The formula is as shown in the specification, wherein R1, R2 and R3 are independently selected from H, F or OCH3. In recent years, 5-serotonin 1A receptor partly excited and selective 5-serotonin reuptake inhibition of the dual role of antidepressants become a hot research focus of novel antidepressants. (H) 5-HT uptake inhibition experiment and h5-HT1A binding affinity experiment in rat synapse show that the compound has 5-HT reuptake inhibition and activating effect on 5-HT1A receptors, and the compound can serve as the drug for treating human central nervous system dysfunction like depression and anxiety.