1608-46-4

Basic information

• Product Name: 1,2-Diiodo-4-nitrobenzene
• Synonyms: 1,2-Diiodo-4-nitrobenzene;Benzene, 1,2-diiodo-4-nitro-
• CAS NO: 1608-46-4
• Molecular Formula: C₆H₃I₂NO₂
• Molecular Weight: 374.90246
• Mol File: 1608-46-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 108-110 °C(Solv: ethanol (64-17-5))
• Boiling Point: 347.6°C at 760 mmHg
• Flash Point: 164°C
• Appearance: /
• Density: 2.578g/cm³
• Vapor Pressure: 0.000107mmHg at 25°C
• Refractive Index: 1.739
• CAS DataBase Reference: 1,2-Diiodo-4-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Diiodo-4-nitrobenzene(1608-46-4)
• EPA Substance Registry System: 1,2-Diiodo-4-nitrobenzene(1608-46-4)

Safety Data

• Hazardous Substances Data: 1608-46-4(Hazardous Substances Data)

Usage

Description

1,2-Diiodo-4-nitrobenzene is a chemical compound characterized by a benzene ring with two iodine atoms and one nitro group attached to it. It is a pale yellow solid that exhibits insolubility in water but is soluble in organic solvents.

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 this compound 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

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.