69113-59-3

Basic information

• Product Name: 3-Iodobenzonitrile
• Synonyms: M-IODOBENZONITRILE;3-IODOBENZONITRILE;1-CYANO-3-IODOBENZENE;3-Cyanoiodobenzene;3-Iodobenzonitrile 98%;1-Iodo-3-cyanobenzene;3-Cyano-1-iodobenzene;3-Iodobenzonitrile,97%
• CAS NO: 69113-59-3
• 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: 69113-59-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 40-43 °C(lit.)
• Boiling Point: 260.1 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: light brown to red crystal
• Density: 1.91 g/cm³
• Vapor Pressure: 0.0125mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• Sensitive: Light Sensitive
• CAS DataBase Reference: 3-Iodobenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Iodobenzonitrile(69113-59-3)
• EPA Substance Registry System: 3-Iodobenzonitrile(69113-59-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-37/39-24/25
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 69113-59-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 69113-59-3 differently. You can refer to the following data:
1. suzuki reaction
2. 3-Iodobenzonitrile may be used as a starting reagent in the synthesis of tetrachloroisophthalo-[14C]-nitrile (TCIN). It may also be used in the preparation of:1-(3-iodophenyl)-3-{2-[4-(trifluoromethyl)-1-piperidinyl]ethyl}-2-imidazolidinonepiperidine derivativechiral amino acid anilide

Synthesis Reference(s)

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

General Description

3-Iodobenzonitrile is a halogenated aromatic nitrile. Its standard (ρ° = 0.1MPa) molar enthalpy of formation was determined by combustion calorimetry.

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

Upstream product

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

Downstream Products

• 696-41-3 m-iodobenzaldehyde 
• 380383-84-6 1-tert-butoxycarbonyl-1-(3-cyanophenyl)hydrazine 
• 1527-89-5 3-methoxybenzonitrile 
• 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 
• 36852-02-5 3,3'-dicyanobiphenyl 
• 100-47-0 benzonitrile 
• 125873-00-9 ethyl (E)-3-(3-cyanophenyl)-2-propenoate 
• 204078-31-9 3-(morpholin-4-yl)benzonitrile 
• 909302-28-9 3-(3-benzylamino-3-methylbut-1-ynyl)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

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.

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.