51628-12-7

Usage

Uses

Used in Organic Syntheses:
4-IODOPHENYLACETONITRILE is used as an intermediate in organic syntheses for its ability to participate in various chemical reactions, such as substitution, addition, and condensation reactions. Its presence in the molecular structure allows for the formation of a wide range of compounds with diverse properties and applications.
Used in Pharmaceutical Industry:
4-IODOPHENYLACETONITRILE is used as an intermediate in the pharmaceutical industry due to its potential role in the development of new drugs and therapeutic agents. Its unique structure can be modified and functionalized to create molecules with specific biological activities, making it a valuable building block in the synthesis of pharmaceutical compounds.

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 
• 79757-98-5 4-bromo-2-bromomethyl-thiophene 
• 624-31-7 4-tolyl iodide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 773837-37-9 sodium cyanide 
• 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 
• 76633-63-1 2-Cyclohexyl-2-(p-iodphenyl)acetonitril 
• 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 
• 630385-11-4 1-(4-iodobenzyl)cyclopropylamine 
• 473736-90-2 tert-butyl 4-cyano-4-(4-iodophenyl)piperidine-1-carboxylate 
• 1196879-28-3 2-(4-iodophenyl)ethanethioamide 
• 1219497-52-5 C₁₀H₁₂IN*ClH 
• 170688-50-3 C₁₆H₁₃NO 
• 1257107-36-0 4-(4-iodophenyl)-tetrahydropyrane-4-carbonitrile 
• 1401660-92-1 7-(diethylamino)-3-(4-(diphenylphosphoryl)phenyl)-2H-chromen-2-one 
• 1401660-93-2 3-(4-(di-p-tolylphosphoryl)phenyl)-7-(diethylamino)-2H-chromen-2-one 
• 1401660-94-3 3-(4-(diphenylphosphoryl)phenyl)-7-methoxy-2H-chromen-2-one 

Relevant academic research and scientific papers

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.

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.

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.

Orally bioavailable factor Xa inhibitors containing alpha-substituted gem-dimethyl P4 moieties

In an effort to identify a potential back-up to apixaban (Eliquis), we explored a series of diversified P4 moieties. Several analogs with substituted gem-dimethyl moieties replacing the terminal lactam of apixaban were identified which demonstrated potent

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.

Synthesis and biological evaluation of meperidine analogues at monoamine transporters

A series of aryl-substituted meperidine analogues was synthesized, and the binding affinities were determined at the DAT, SERT, and NET as well as at μ-opioid receptors. Generally the analogues exhibited increased affinity for the DAT and SERT relative to

COPPER-CATALYZED FORMATION OF CARBON-HETEROATOM AND CARBON-CARBON BONDS

One aspect of the present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-sulfur bond between the sulfur atom of a thiol moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper(II)-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-carbon bond between the carbon atom of cyanide ion and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In another embodiment, the present invention relates to a copper-catalyzed method of transforming and aryl, heteroaryl, or vinyl iodide. Yet another embodiment of the present invention relates to a tandem method, which may be practiced in a single reaction vessel, wherein the first step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl iodide from the corresponding aryl, heteroaryl, or vinyl chloride or bromide; and the second step of the method involves the copper-catalyzed formation of an aryl, heteroaryl, or vinyl nitrile, amide or sulfide from the aryl, heteroaryl, or vinyl iodide formed in the first step.

1,1-DISUBSTITUTED CYCLOALKYL DERIVATIVES AS FACTOR XA INHIBITORS

The present application describes 1,1-disubstituted cycloalkyl compounds and derivatives thereof, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of factor Xa.

Copper-catalyzed halogen exchange in aryl halides: An aromatic finkelstein reaction

A mild and general method for the conversion of aryl, heteroaryl, and vinyl bromides into the corresponding iodides was developed utilizing a catalyst system comprising 5 mol % of Cul and 10 mol % of a 1,2- or 1,3-diamine ligand. A variety of polar functional groups are tolerated, and even N-H containing substrates such as sulfonamides, amides, and indoles are compatible with the reaction conditions. Both the reaction rate and the equilibrium conversion of the aryl bromide depend on the choice of the halide salt and the solvent. The best results were obtained using Nal as the halide salt and dioxane, n-butanol, or n-pentanol as the solvents. Copyright

Stilbene derivative and stilbene analog derivative, and use thereof

The present invention relates to a novel compound having a 12-lipoxygenase inhibitory effect, of the general formula (I), a precursor thereof, and a medicine containing the same, STR1 wherein R1 represents a hydrogen atom or a hydroxy group; on