1608-46-4

Usage

Uses

Used in Organic Synthesis:
1,2-Diiodo-4-nitrobenzene is utilized as a reagent in organic synthesis for the preparation of various organic compounds. Its unique structure allows it to participate in a range of chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Dye Manufacturing:
In the dye industry, 1,2-Diiodo-4-nitrobenzene is employed as a precursor to synthesize different types of dyes. Its chemical properties contribute to the formation of dyes with specific color characteristics and stability.
Used in Pharmaceutical Production:
1,2-Diiodo-4-nitrobenzene also serves as a precursor in the manufacturing of pharmaceuticals. Its role in the synthesis of certain drugs highlights its importance in the development of new medications and therapies.
Safety Precautions:
Due to its toxic nature, 1,2-Diiodo-4-nitrobenzene is considered harmful if swallowed, inhaled, or comes into contact with the skin. It is crucial to follow appropriate safety measures and handling protocols when working with 1,2-Diiodo-4-nitrobenzene to minimize health risks and ensure a safe working environment.

InChI:InChI=1/C6H3I2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H

Upstream product

• 619-17-0 4-Nitroanthranilic acid 
• 636-98-6 p-nitrobenzene iodide 
• 6293-83-0 2-iodo-4-nitrophenylamine 

Downstream Products

• 100381-78-0 1-(2-iodo-4-nitro-phenoxy)-4-methoxy-benzene 
• 855394-50-2 1-ethoxy-4-(2-iodo-4-nitro-benzenesulfonyl)-benzene 
• 6293-83-0 2-iodo-4-nitrophenylamine 
• 1602-62-6 1,2-Dijod-4,6-dinitro-benzol 
• 1602-63-7 1,2-diiodo-3,4-dinitro-benzene 
• 42016-95-5 3,4-diiodo-aniline 
• 859313-33-0 2-benzyloxy-1-(2-iodo-4-nitro-phenylsulfanyl)-4-nitro-benzene 
• 96460-61-6 2-iodo-4-(2-iodo-4-nitro-phenoxy)-1-methoxy-benzene 
• 875227-72-8 1-ethoxy-4-(2-iodo-4-nitro-phenylsulfanyl)-benzene 

Relevant academic research and scientific papers

Formation of arenes via diallylarenes: Strategic utilization of Suzuki-Miyaura cross-coupling, Claisen rearrangement and ring-closing metathesis

Two new synthetic strategies for benzoannulation are reported. The first strategy is based on the Suzuki-Miyaura cross-coupling reaction. To this end, various ortho-diallylbenzene derivatives were prepared from the corrresponding diiodo derivatives by an allylation strategy using an allylboronate as coupling partner. These diallyl derivatives were subjected to a ring-closing metathesis (RCM) and one-pot dichlorodicyanoquinone (DDQ) oxidation sequence to deliver 2-substituted naphthalenes. In the second strategy, a double Claisen rearrangement and RCM protocol have been used as key steps to give highly functionalized benzoannulated quinone derivatives.

A new, one-step, effective protocol for the iodination of aromatic and heterocyclic compounds via aprotic diazotization of amines

We have developed a convenient one-step preparation of aromatic and some heterocyclic iodides by the sequential diazotization-iodination of the aromatic amines with a KI/NaNO2/p-TsOH system in acetonitrile at room temperature. This method has general character and allows aryl iodides with either donor or acceptor substituents in various positions to be obtained from the corresponding amines in 50-90% yield. Georg Thieme Verlag Stuttgart.

Easy, inexpensive and effective oxidative iodination of deactivated arenes in sulfuric acid

Two 'model' deactivated arenes, benzoic acid and nitrobenzene, were effectively monoiodinated within 1 h at 25-30 °C, with strongly electrophilic I+ reagents, prior prepared from diiodine and various oxidants (CrO3, KMnO4, active MnO2, HIO 3, NaIO3, or NaIO4) in 90% (v/v) concd sulfuric acid (ca. 75 mol% H2SO4). Next, an I2/ NaIO3/90% (v/v) concd H2SO4 exemplary system was used to effectively mono- or diiodinate a number of deactivated arenes. All former papers dealing with the direct iodination of deactivated arenes are briefly reviewed.

Iodination of nitroarenes by a superactive reagent based on iodine chloride

Iodine chloride reacts with Ag2SO4 in H2SO4 to give a new superelectrophilic reagent capable of iodinating nitrobenzene, halogenated nitrobenzenes, nitrotoluenes, and aromatic compounds with two nitro groups in the ring. Mononitroarenes are easily iodinated at 0-20 deg C, while dinitroarenes require heating to 100-170 deg C.

Preparation of N-Substituted Phthalimides by Palladium-Catalyzed Carbonylation and Coupling of o-Dihalo Aromatics and Primary Amines

A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines.Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115 deg C, 90 psi of CO, 3 percent PdCl2L2, and 2.4 equiv of DBU.This process is tolerant of a wide variety of functional groups and gives good yields of the desired products.Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction.The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.