51628-12-7

Basic information

• Product Name: 4-IODOPHENYLACETONITRILE
• Synonyms: 4-Iodophenylacetonitrile 4-Iodobenzyl Cyanide p-Iodobenzyl Cyanide;p-IodobenzylCyanide;2-(4-iodophenyl)acetonitrile;2-(4-iodophenyl)ethanenitrile;4-Iodophenylacetonitrile 97%;4-IODOBENZYL CYANIDE;4-IODOPHENYLACETONITRILE
• CAS NO: 51628-12-7
• Molecular Formula: C₈H₆IN
• Molecular Weight: 243.04
• EINECS: -0
• Mol File: 51628-12-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 53-57 °C(lit.)
• Boiling Point: 152°C/ 3mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.764 g/cm³
• Vapor Pressure: 0.00275mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• Sensitive: Light Sensitive
• BRN: 1934479
• CAS DataBase Reference: 4-IODOPHENYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-IODOPHENYLACETONITRILE(51628-12-7)
• EPA Substance Registry System: 4-IODOPHENYLACETONITRILE(51628-12-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-43
• Safety Statements: 36/37
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 51628-12-7(Hazardous Substances Data)

Usage

Uses

4-Iodophenylacetonitrile is used as an intermediate in organic syntheses and in pharmaceuticals.

InChI:InChI=1/C8H6IN/c9-8-3-1-7(2-4-8)5-6-10/h1-4H,5H2

Upstream product

• 16004-15-2 1-bromomethyl-4-iodobenzene 
• 151-50-8 potassium cyanide 
• 54589-53-6 4-iodobenzyl chloride 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 624-31-7 4-tolyl iodide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 773837-37-9 sodium cyanide 
• 79757-98-5 4-bromo-2-bromomethyl-thiophene 
• 16532-79-9 4-Bromophenylacetonitrile 

Downstream Products

• 107154-93-8 2-(4-iodo-phenyl)-3c-(4,5,6,7-tetrahydro-benzo[b]thiophen-2-yl)-acrylonitrile 
• 1798-06-7 (4-iodophenyl)acetic acid 
• 73918-57-7 p-Iodophenylethylamine 
• 102027-83-8 1,1,1-trichloro-2,2-bis-[2-(4-iodo-phenyl)-acetylamino]-ethane 
• 117417-09-1 [4-((E)-2-Bromo-vinyl)-phenyl]-acetonitrile 
• 258500-75-3 2-(4-iodophenyl)-2-(2,2-dimethoxyethyl)-4,4-dimethoxybutyronitrile 
• 176860-58-5 N-Hydroxy-2-(4-iodo-phenyl)-acetamidine 
• 138500-86-4 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetonitrile 
• 473736-90-2 tert-butyl 4-cyano-4-(4-iodophenyl)piperidine-1-carboxylate 
• 70124-90-2 2-(4-((trifluoromethyl)thio)phenyl)acetonitrile 
• 1094247-58-1 cyclohexyl(4-iodophenyl)methanone 
• 1449744-22-2 1-(4-iodophenyl)cyclohexanecarbaldehyde 
• 1260788-11-1 1-(4-iodophenyl)cyclohexanecarbonitrile 
• 1448466-77-0 3-dimethylamino-2-(4-iodophenyl)acrylonitrile 

Relevant articles and documents

Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

A highly efficient, direct C(sp3)-H cyanation was developed under mild photocatalytic conditions. The method enabled the direct cyanation of various C(sp3)-H substrates with excellent functional group tolerance. Notably, complex natural products and bioactive compounds were efficiently cyanated.

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.

Synthesis of pyrazolo[1,5-a][1,3,5]triazine derivatives as inhibitors of thymidine phosphorylase

Thymidine phosphorylase (TP) is an enzyme that promotes tumor growth and metastasis and therefore is an attractive druggable target. Using a reported TP inhibitor, 7-deazaxanthine (7DX), as the lead compound; this study was set up to evaluate whether pyrazolo[1,5-a][1,3,5]triazin-2,4-diones and pyrazolo[ 1,5- a][1,3,5]triazin-2-thioxo-4-ones would exhibit TP inhibitory activity. The pyrazolo[1,5-a][1,3,5] triazine nucleus was constructed using a reaction that annulated the 1,3,5-triazine ring onto a pyrazole scaffold. Among the 52 compounds synthesized and tested, it was found that 1,3-dihydro-pyrazolo[1,5-a] [1,3,5]triazin-2-thioxo-4-ones exhibited various extent of inhibitory activity against TP. The best compound 17p, which bears a para-substituted pentafluorosulfur group, showed an IC50 value of 0.04 μM, which was around 800 times more potent than the 7DX (IC50 = 32 μM) under the same bioassay conditions. The results of the study suggested that a substituent with +σ and +π properties inserted at position 4 of a phenyl ring that is attached to position 8 of the pyrazolo[1,5-a][1,3,5]triazin- 2-thioxo-4-one scaffold would give excellent TP inhibitory action. In addition, 17p was found to be a non-competitive inhibitor thus suggested that it might interact with TP at a position different from the substrate binding site.