3058-39-7

Basic information

• Product Name: 4-Iodobenzonitrile
• Synonyms: 4-Iodobenzonitrile ,98%;4-lodobenzonitrile;Benzonitrile of iodine;4-Iodobenzonitrile, 99% 25GR;On iodobenzene nitrile;Benzonitrile, 4-iodo-;On ioxynil;4-iodo-benzonitril
• CAS NO: 3058-39-7
• Molecular Formula: C₇H₄IN
• Molecular Weight: 229.02
• Product Categories: Building Blocks;C6 to C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Aromatic Nitriles;API intermediates;Iodine Compounds;Nitriles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 3058-39-7.mol
• Article Data: 106

Chemical Properties

• Melting Point: 124-128 °C(lit.)
• Boiling Point: 271.6 °C at 760 mmHg
• Flash Point: 118 °C
• Appearance: Light yellow-brown/Powder or Chunks
• Density: 1.9241 (estimate)
• Vapor Pressure: 0.00639mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• CAS DataBase Reference: 4-Iodobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Iodobenzonitrile(3058-39-7)
• EPA Substance Registry System: 4-Iodobenzonitrile(3058-39-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-36/37/39-26
• RIDADR: 3439
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 3058-39-7(Hazardous Substances Data)

Usage

Description

4-Iodobenzonitrile is a light yellow crystal powder that is widely utilized in various chemical reactions and industries due to its unique properties.

Uses

Used in Organic Synthesis:
4-Iodobenzonitrile is used as a catalytic agent in organic synthesis, facilitating various chemical reactions and contributing to the formation of desired products.
Used in Petrochemical Industry:
In the petrochemical industry, 4-Iodobenzonitrile is employed as an additive, enhancing the performance and properties of the final products.
Used in Suzuki Reaction:
4-Iodobenzonitrile plays a significant role in the Suzuki reaction, a widely used method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds.
Used in the Synthesis of Ethyl-4′-cyano-4-nitro[1,1′-biphenyl]-2-carboxylate:
4-Iodobenzonitrile is used as a starting material in a multi-step reaction process to synthesize ethyl-4′-cyano-4-nitro[1,1′-biphenyl]-2-carboxylate, which has potential applications in the pharmaceutical and chemical industries.
Used in the Synthesis of 2-(4-cyanophenyl)tellurophene:
4-Iodobenzonitrile is utilized in the Stille coupling reaction with tellurophene to produce 2-(4-cyanophenyl)tellurophene, a compound with potential applications in the field of organic electronics.
Used in the Synthesis of 2,5-bis(4-cyanophenyl)tellurophene:
In a similar manner, 4-Iodobenzonitrile is used in the Stille coupling reaction with 2,5-bis(trimethylstannyl)tellurophene to synthesize 2,5-bis(4-cyanophenyl)tellurophene, another compound with potential applications in organic electronics.
Used in the Synthesis of Ethyl-4′-cyano-6-[(E)-phenylmethylidene]amino[1,1′-biphenyl]-3-carboxylate:
4-Iodobenzonitrile is also used as a starting material in a multi-step reaction process to synthesize ethyl-4′-cyano-6-[(E)-phenylmethylidene]amino[1,1′-biphenyl]-3-carboxylate, a compound with potential applications in various industries, including pharmaceuticals and materials science.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1327, 1988 DOI: 10.1080/00397918808078799Tetrahedron Letters, 35, p. 5539, 1994 DOI: 10.1016/S0040-4039(00)77241-8

InChI:InChI=1/C7H4IN/c8-7-3-1-6(5-9)2-4-7/h1-4H

Upstream product

• 3956-07-8 4-iodobenzamide 
• 540-37-4 p-aminoiodobenzene 
• 619-65-8 4-cyanobenzoic Acid 
• 624-38-4 para-diiodobenzene 
• 139-02-6 sodium phenoxide 
• 81447-73-6 (4-Cyano-phenyl)-phenyl-iodonium 
• 79664-67-8 4-(3,3-diethyltriaz-1-en-1-yl)benzonitrile 
• 100-47-0 benzonitrile 
• 108-95-2 phenol 
• 873-74-5 4-Aminobenzonitrile 
• 623-00-7 4-bromobenzenecarbonitrile 
• 2246-51-7 bis-(4-cyano-benzoyl)-peroxide 
• 826-04-0 4-dichloroiodanyl-benzonitrile 
• 336866-07-0 bis(2-hydroxy-1,1,2-trimethylpropyl)cyanoboronate 

Downstream Products

• 619-58-9 4-iodobenzoic acid 
• 826-04-0 4-dichloroiodanyl-benzonitrile 
• 101420-79-5 4-iodo-3-nitrobenzonitrile 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 5969-45-9 4-Iod-dithiobenzoesaeure-methylester 
• 10270-27-6 1-(4-cyanophenyl)-2-phenylethane 
• 29822-79-5 4-(2-phenylethynyl)benzonitrile 
• 15961-46-3 4-(2-thienyl)benzonitrile 
• 492-97-7 2,2'-Bithiophene 
• 79149-55-6 2-(4-cyanophenyl)-N,N-dimethylacetamide 
• 130138-50-0 [Cyano-(4-cyano-phenyl)-methyl]-phosphonic acid diethyl ester 
• 143925-52-4 N-(2-Fluoro-phenyl)-4-methoxy-benzamide 
• 58949-75-0 4-(2-oxopropyl)benzonitrile 
• 51238-46-1 4-(phenylthio)benzonitrile 

Relevant articles and documents

Revealing resonance effects and intramolecular dipole interactions in the positional isomers of benzonitrile-core thermally activated delayed fluorescence materials

We report on the properties of the three positional isomers of (2,7-di-tert-butyl-9,9-dimethylacridin-10(9H)-yl)benzonitrile, which are found to have comparable donor steric environments and donor-acceptor dihedral angles. An unexpected intramolecular dip

Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions

A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.

Water-Dispersible Pd–N-Heterocyclic Carbene Complex Immobilized on Magnetic Nanoparticles as a New Heterogeneous Catalyst for Fluoride-Free Hiyama, Suzuki–Miyaura and Cyanation Reactions in Aqueous Media

Abstract: Pd–N-heterocyclic carbine complex immobilized on magnetic nanoparticles is synthesized and characterized by different techniques such as FT-IR, XPS, TEM, EDX, FESEM, VSM, TGA, and ICP. The synthesized catalyst was used as a new water dispersible heterogeneous catalyst in the fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water. By this method, different types of biaryls and aryl nitriles were synthesized in good to high yields by the reaction of a variety of aryl iodides, bromides and chlorides with triethoxyphenylsilane, phenylboronic acid and K4[Fe(CN)6]·3H2O, respectively. The presence of sulfonates as hydrophilic groups on the surface of the catalyst confers a highly water dispersible, active and yet magnetically recoverable Pd catalyst. The possibility to perform the reaction in water as a green medium, ease of the catalyst recovery and reuse by magnetic separation, and the absence of any additives or co-solvents make this method as an eco-friendly and economical protocol for the synthesis of biaryl derivatives and aryl nitriles. Graphic Abstract: A new water dispersible heterogeneous Pd–N-heterocyclic carbene for the efficient fluoride-free Hiyama, Suzuki–Miyaura and cyanation reactions in pure water is developed.[Figure not available: see fulltext.].