69113-59-3

Usage

Uses

Used in Chemical Synthesis:
3-Iodobenzonitrile is utilized as a starting reagent in various chemical synthesis processes. It plays a crucial role in the synthesis of tetrachloroisophthalo-[14C]-nitrile (TCIN), a compound that may have applications in different chemical research and industrial processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Iodobenzonitrile is used as a key intermediate in the preparation of specific drug molecules. It contributes to the synthesis of 1-(3-iodophenyl)-3-2-[4-(trifluoromethyl)-1-piperidinyl]ethyl-2-imidazolidinonepiperidine derivative, a compound with potential therapeutic applications.
Used in Chiral Chemicals Production:
3-Iodobenzonitrile is also employed in the production of chiral amino acid anilide, an important class of chiral compounds that are vital in various chemical and pharmaceutical applications, including the development of enantiomerically pure drugs.
Used in Suzuki Reaction:
3-Iodobenzonitrile may be involved in the Suzuki reaction, a type of cross-coupling reaction used in organic chemistry to form carbon-carbon bonds. This reaction is widely used in the synthesis of various organic compounds, including pharmaceuticals and natural products, making 3-Iodobenzonitrile a valuable reagent in this context.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 3552, 1990 DOI: 10.1021/jo00298a032

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

Upstream product

• 100-47-0 benzonitrile 
• 108-95-2 phenol 
• 6952-59-6 3-cyanobromobenzene 
• 618-51-9 3-Iodobenzoic acid 
• 2237-30-1 m-cyanoaniline 
• 33348-34-4 4-amino-3-iodobenzonitrile 
• 696-40-2 3-iodobenzylamine 
• 10388-19-9 m-iodobenzamide 
• 139-02-6 sodium phenoxide 
• 81447-70-3 m-cyanodiphenyliodonium iodide 

Downstream Products

• 696-41-3 m-iodobenzaldehyde 
• 13428-06-3 3-(hydroxy(phenyl)methyl)benzonitrile 
• 1527-89-5 3-methoxybenzonitrile 
• 92367-52-7 3-n-butoxybenzonitrile 
• 458550-46-4 ethyl 4-(3-cyanoanilino)benzoate 
• 458550-45-3 3-(4-bromoanilino)benzonitrile 
• 55669-57-3 3-Cyanoazobenzol 
• 4350-51-0 3-(pyridine-2-yl)benzonitrile 
• 679390-77-3 4-[(Z)-1-(3-Cyano-phenyl)-2-trimethylsilanyl-vinyl]-benzoic acid ethyl ester 
• 6136-62-5 3-benzoylbenzonitrile 

Relevant academic research and scientific papers

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

One-Pot, Metal-Free Conversion of Anilines to Aryl Bromides and Iodides

A metal-free synthesis of aryl bromides and iodides from anilines via halogen abstraction from bromotrichloromethane and diiodomethane is described. This one-pot reaction affords aryl halides from the corresponding anilines in moderate to excellent yields without isolation of diazonium salts. The transformation has short reaction times, a simple workup, and insensitivity to moisture and air and avoids excess halogenation. DFT calculations support a SRN1 mechanism. This method represents a convenient alternative to the classic Sandmeyer reaction.

Salicylic Acid-Catalyzed One-Pot Hydrodeamination of Aromatic Amines by tert-Butyl Nitrite in Tetrahydrofuran

A significant acceleration in the hydrodeamination of in situ formed diazonium salts (from aromatic amines) has been observed in the presence of 10-mol% salicylic acid, using tetrahydrofuran as the hydrogen donor. The reaction proceeds efficiently at 20 °C for a wide range of substituted anilines, even at 10-mmol scale, without any other additive. The same protocol has been adapted to the selective deuterodeamination of some aromatic amines. Control experiments clearly show that aryl radicals are involved in the reaction mechanism. (Figure presented.).

Photo-induced Metal-Catalyst-Free Aromatic Finkelstein Reaction

The facile iodination of aromatic compounds under mild conditions is a great challenge for both organic and medicinal chemistry. Particularly, the synthesis of functionalized aryl iodides by light has long been considered impossible due to their photo-lability, which actually makes aryl iodides popular starting materials in many photo-substitution reactions. Herein, a photo-induced halogen exchange in aryl or vinyl halides has been discovered for the first time. A broad scope of aryl iodides can be prepared in high yields at room temperature under exceptionally mild conditions without any metal or photo-redox catalysts. The presence of a catalytic amount of elemental iodine could promote the reaction significantly.

Rapid and efficient copper-catalyzed finkelstein reaction of (hetero)aromatics under continuous-flow conditions

A general, rapid, and efficient method for the copper-catalyzed Finkelstein reaction of (hetero)aromatics has been developed using continuous flow to generate a variety of aryl iodides. The described method can tolerate a broad spectrum of functional groups, including N-H and O-H groups. Additionally, in lieu of isolation, the aryl iodide solutions were used in two distinct multistep continuous-flow processes (amidation and Mg-I exchange/nucleophilic addition) to demonstrate the flexibility of this method.

Cu/nitroxyl-catalyzed aerobic oxidation of primary amines into nitriles at room temperature

An efficient catalytic method has been developed for aerobic oxidation of primary amines to the corresponding nitriles. The reactions proceed at room temperature and employ a catalyst consisting of (4,4′-tBu 2bpy)CuI/ABNO (ABNO = 9-azabicyclo[3.3.1]nonan-3-one-N-oxyl). The reactions exhibit excellent functional group compatibility and substrate scope and are effective with benzylic, allylic, and aliphatic amines. Preliminary mechanistic studies suggest that aerobic oxidation of the Cu catalyst is the turnover-limiting step of the reaction.

A safe and reliable procedure for the iododeamination of aromatic and heteroaromatic amines in a continuous flow reactor

A method for the safe and reliable iododeamination of aromatic and heteroaromatic amines under copper-free conditions is described and its scope is evaluated.

Iodination of aryl amines in a water-paste form via stable aryl diazonium tosylates

The diazotization of aryl amines at room temperature in paste form with NaNO2, p-TsOH and a small amount of water, followed by treatment with KI provides a new, simple, and effective route for the preparation of various aryl iodides. The water-paste and strong acid-free reaction conditions are environmentally friendly and compatible with acid-sensitive functional groups.

A Novel Aromatic Iodination Method Using F2

A new method for direct aromatic iodination with IF, made in situ from the corresponding elements, is described.Depending on the reaction time and temperature, mono- or polyiodination can be achieved.Even deactivated aromatic rings can be directly iodinated without the presence of any Friedel-Crafts catalyst.Sensitive groups such as aromatic aldehydes are not affected by the reagent.