624-38-4

Basic information

• Product Name: 1,4-Diiodobenzene
• Synonyms: 1,4-DIIODOBENZENE;4-DIIODOBENZENE;P-DIIODOBENZENE;1,4-diiodbenzene;1,4-diiodo-benzen;Benzene, 1,4-iodo-;Benzene, p-diiodo-;Benzene,1,4-diiode-
• CAS NO: 624-38-4
• Molecular Formula: C₆H₄I₂
• Molecular Weight: 329.9
• EINECS: 210-842-2
• Product Categories: Iodine Compounds;Aryl;C6;Halogenated Hydrocarbons;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 624-38-4.mol
• Article Data: 91

Chemical Properties

• Melting Point: 131-133 °C(lit.)
• Boiling Point: 285 °C(lit.)
• Flash Point: 285°C
• Appearance: White to beige/Crystalline Powder
• Density: 2.350
• Vapor Pressure: 0.00495mmHg at 25°C
• Refractive Index: 1.6212
• Storage Temp.: Store below +30°C.
• Water Solubility: Soluble in ether and ethanol. Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 1904546
• CAS DataBase Reference: 1,4-Diiodobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Diiodobenzene(624-38-4)
• EPA Substance Registry System: 1,4-Diiodobenzene(624-38-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8
• TSCA: Yes
• Hazardous Substances Data: 624-38-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 624-38-4 differently. You can refer to the following data:
1. suzuki reaction
2. 1,4-Diiodobenzene is used in Suzuki reaction. It is used as a precursor in the preparation of martinellic acid and 1,4-bis(p-R-phenylethynyl)benzenes. Further, it is employed in the preparation of 1,4-diiodo-2,5-didodecylbenzene , which is a starting reagent for the synthesis of oligo(1,4-phenylene ethynylene). It is also used in human and animal nutrition products including antiseptics and disinfectants. In addition to this, it used in polarizing films for liquid crystal display chemicals.

Purification Methods

Crystallise it from EtOH or boiling MeOH, then dry it in air. [Beilstein 5 IV 700.]

InChI:InChI=1/C6H4I2/c7-5-1-2-6(8)4-3-5/h1-4H

Upstream product

• 591-50-4 iodobenzene 
• 532-32-1 sodium benzoate 
• 1578-33-2 2-furyltrimethylsilane 
• 73178-09-3 -p-iodobenzene 
• 540-37-4 p-aminoiodobenzene 
• 536-80-1 iodosylbenzene 
• 110-83-8 cyclohexene 
• 71-43-2 benzene 
• 7664-93-9 sulfuric acid 
• 7553-56-2 iodine 
• 64-19-7 acetic acid 
• 7697-37-2 nitric acid 
• 7732-18-5 water 
• 7782-68-5 iodic acid 

Downstream Products

• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 591-50-4 iodobenzene 
• 352-34-1 4-fluoro-1-iodobenzene 
• 150-76-5 4-methoxy-phenol 
• 150-78-7 1,4-dimethoxybezene 
• 623-26-7 terephthalonitrile 
• 886-82-8 1,4-Bis--benzol 
• 74-88-4 methyl iodide 
• 1486-01-7 biphenyl-d10 
• 78486-59-6 1,4-di(phenyl-d5)benzene 
• 114833-01-1 C₂₂H₁₄O₆ 
• 3058-39-7 4-iodobenzonitrile 
• 71-43-2 benzene 

Relevant articles and documents

Transition-Metal-Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles

A chemoselective C(sp2)?C(sp2) coupling of sufficiently electron-deficient fluorinated arenes and functionalized N-aryl-N’-silyldiazenes as masked aryl nucleophiles is reported. The fluoride-promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (SNAr). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.

Boosting Low-Valent Aluminum(I) Reactivity with a Potassium Reagent

The reagent RK [R=CH(SiMe3)2 or N(SiMe3)2] was expected to react with the low-valent (DIPPBDI)Al (DIPPBDI=HC[C(Me)N(DIPP)]2, DIPP=2,6-iPr-phenyl) to give [(DIPPBDI)AlR]?K+. However, deprotonation of the Me group in the ligand backbone was observed and [H2C=C(N-DIPP)?C(H)=C(Me)?N?DIPP]Al?K+ (1) crystallized as a bright-yellow product (73 %). Like most anionic AlI complexes, 1 forms a dimer in which formally negatively charged Al centers are bridged by K+ ions, showing strong K+???DIPP interactions. The rather short Al–K bonds [3.499(1)–3.588(1) ?] indicate tight bonding of the dimer. According to DOSY NMR analysis, 1 is dimeric in C6H6 and monomeric in THF, but slowly reacts with both solvents. In reaction with C6H6, two C?H bond activations are observed and a product with a para-phenylene moiety was exclusively isolated. DFT calculations confirm that the Al center in 1 is more reactive than that in (DIPPBDI)Al. Calculations show that both AlI and K+ work in concert and determines the reactivity of 1.

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.