4387-36-4

Basic information

• Product Name: 2-Iodobenzonitrile
• Synonyms: 1-CYANO-2-IODOBENZENE;2-IODOBENZONITRILE;O-IODOBENZONITRILE;2-iodobenzontirlle;2-Iodobenzonitrile,99%;2-lodobenzonitrile;Nitrile o-iodobenzene;2-Iodobenzonitrile 97%
• CAS NO: 4387-36-4
• Molecular Formula: C₇H₄IN
• Molecular Weight: 229.02
• Product Categories: Aromatic Nitriles;Nitrile;Iodine Compounds;Nitriles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C6 to C7;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4387-36-4.mol
• Article Data: 35

Chemical Properties

• Melting Point: 52-54°C
• Boiling Point: 147 °C / 15mmHg
• Flash Point: 110 °C
• Appearance: Yellow/Solid
• Density: 1.91 g/cm³
• Vapor Pressure: 0.00323mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• CAS DataBase Reference: 2-Iodobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodobenzonitrile(4387-36-4)
• EPA Substance Registry System: 2-Iodobenzonitrile(4387-36-4)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-36-22
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: IRRITANT-HARMFUL
• PackingGroup: III
• Hazardous Substances Data: 4387-36-4(Hazardous Substances Data)

Usage

Description

2-Iodobenzonitrile is a nitrile compound characterized by the presence of both a cyano group and an aryl carbon-iodide bond in adjacent positions on a benzene ring. It is a yellow solid and is recognized for its excellent reactivity, making it a valuable intermediate in organic synthetic chemistry.

Uses

Used in Organic Synthesis:
2-Iodobenzonitrile is used as a key intermediate in the field of organic synthesis due to its reactivity and the presence of functional groups that facilitate various chemical reactions. Its utility in this application stems from the ability to undergo a wide range of reactions, such as the Suzuki reaction, which is a widely used method for the formation of carbon-carbon bonds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Iodobenzonitrile is utilized as a building block for the synthesis of various medicinal compounds. Its unique structure allows for the creation of diverse drug candidates with potential therapeutic applications.
Used in Pesticide Industry:
2-Iodobenzonitrile is also employed in the development of pesticides, where its reactivity and structural features contribute to the design of effective and targeted pest control agents.
Used in Dye Industry:
2-Iodobenzonitrile finds application in the dye industry, where it serves as an intermediate for the production of various dyes with specific color properties and characteristics.
Used in Fine Chemicals:
2-Iodobenzonitrile is used as an intermediate in the synthesis of fine chemicals, which are high-purity chemicals with specialized applications in various industries, including electronics, fragrances, and flavors.

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

Upstream product

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• 1829-28-3 ethyl 2-iodobenzoate 
• 615-37-2 ortho-methylphenyl iodide 
• 88-67-5 2-Iodobenzoic acid 
• 100-47-0 benzonitrile 
• 825-50-3 2-Cyan-1-jod-benzol-dichlorid 
• 2042-37-7 o-cyanobromobenzene 
• 108-95-2 phenol 
• 3930-83-4 o-iodobenzamide 
• 615-42-9 1,2-Diiodobenzene 
• 615-43-0 2-iodophenylamine 

Downstream Products

• 825-50-3 2-Cyan-1-jod-benzol-dichlorid 
• 889686-62-8 2-{[6-(2,4-difluorophenyl)-2-naphthyl]thio}benzonitrile 
• 149989-78-6 2-NCC₆H₄CH₂B(OCMe₂)2 
• 1174070-12-2 2-[(2E)-3-phenylprop-2-en-1-yl]benzonitrile 
• 1415581-19-9 2-(3-phenyl-1H-pyrazol-1-yl)benzonitrile 
• 4492-01-7 1,3-diphenyl-1H-pyrazole 
• 1885-29-6 anthranilic acid nitrile 
• 351862-56-1 2-(2-(4-methoxyphenyl)ethynyl)benzonitrile 
• 905914-49-0 tert-butyl 2-(2,5-cyclohexadien-1-yl)benzylcarbamate 
• 872052-28-3 [(R,R)-2-(2-iodophenyl)-5-methyl-4,5-dihydrooxazol-4-yl]methanol 
• 872052-32-9 [(R,R)-2-(2-iodophenyl)-5-phenyl-4,5-dihydrooxazol-4-yl]methanol 
• 61463-61-4 2-allylbenzonitrile 

Relevant articles and documents

An Air-Stable N-Heterocyclic [PSiP] Pincer Iron Hydride and an Analogous Nitrogen Iron Hydride: Synthesis and Catalytic Dehydration of Primary Amides to Nitriles

An air-stable N-heterocyclic PSiP pincer iron hydride FeH(PMe3)2(SiPh(NCH2PPh2)2C6H4) (4) was synthesized by Si-H activation of a Ph-substituted [PSiP] pincer ligand. The analogous strong electron-donating iPr-substituted [PSiP] pincer ligand was prepared and introduced into iron complex to give an iron nitrogen complex FeH(N2)(PMe3)(SiPh(NCH2PiPr2)2C6H4) (6). Both 4 and 6 showed similar high efficiency for catalytic dehydration of primary amides to nitriles. Air-stable iron hydride 4 was the best catalyst for its stabilization and convenient preparation. A diverse range of cyano compounds including aromatic and aliphatic species was obtained in moderate to excellent yields. A plausible catalytic reaction mechanism was proposed.

A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2

A new transition-metal-free one-pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.

Dehydration of primary amides to nitriles catalyzed by [CNC]-pincer hydrido cobalt(III) complexes

The dehydration reactions from primary amides to nitriles were catalyzed by the [CNC]-pincer hydrido cobalt(III) complexes [(ortho-F4C6–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (1), [(2,5-F2C6H2–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (2) and [(2,4,5-F3C6H–CH[dbnd]N–C10H6)Co(III)(H)(PMe3)2] (3) as catalysts with (EtO)3SiH as an efficient reducing agent. These hydrido cobalt(III) complexes as catalysts are suitable for many substrates and have good functional group tolerance. Among the three cobalt hydrides, complex 2 is the best catalyst. This is the first hydrido cobalt complex-catalyzed dehydration of primary amides to nitriles.