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 
• 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 
• 623-03-0 4-Cyanochlorobenzene 
• 66107-32-2 4-cyanophenyl trifluoromethanesulfonate 
• 137066-22-9 4-cyanobenzenediazonium 4-methylbenzenesulfonate 

Downstream Products

• 10270-27-6 1-(4-cyanophenyl)-2-phenylethane 
• 15961-46-3 4-(2-thienyl)benzonitrile 
• 492-97-7 2,2'-Bithiophene 
• 79149-55-6 2-(4-cyanophenyl)-N,N-dimethylacetamide 
• 143925-52-4 N-(2-Fluoro-phenyl)-4-methoxy-benzamide 
• 51238-46-1 4-(phenylthio)benzonitrile 
• 145050-86-8 2-[(4-Cyano-phenyl)-cyclohexyl-methyl]-malonic acid diethyl ester 
• 1503-49-7 p-cyanobenzophenone 
• 3435-51-6 4-ethenylbenzonitrile 
• 2920-38-9 4-cyano-1,1'-biphenyl 
• 29822-79-5 4-(2-phenylethynyl)benzonitrile 
• 58743-77-4 4'-methoxybiphenyl-4-carbonitrile 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 619-65-8 4-cyanobenzoic Acid 

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.

Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**

The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.