19619-22-8

Usage

Uses

Used in Dye and Pigment Production:
2,4-dicyanoaniline is used as a chemical intermediate for the production of dyes and pigments, owing to its ability to form stable and vibrant color compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2,4-dicyanoaniline serves as a key building block in the synthesis of various medicinal compounds, leveraging its strong electron-withdrawing characteristics to enhance the reactivity and efficacy of the resulting drugs.
Used in Organic Chemistry Reactions:
2,4-dicyanoaniline is utilized as a reagent in organic chemistry, where its electron-withdrawing nature facilitates a range of reactions, including electrophilic substitutions and other transformations.
Used as a Corrosion Inhibitor in Industrial Processes:
2,4-dicyanoaniline is employed as a corrosion inhibitor, protecting metal surfaces from degradation in various industrial applications, thereby extending the service life of equipment and reducing maintenance costs.
Used in the Production of Materials:
2,4-dicyanoaniline is used as a building block in the manufacturing of materials such as plastics, resins, and adhesives, where its chemical properties contribute to the desired physical and chemical characteristics of the final products.

InChI:InChI=1/C8H5N3/c9-4-6-1-2-8(11)7(3-6)5-10/h1-3H,11H2

Upstream product

• 33348-34-4 4-amino-3-iodobenzonitrile 
• 557-21-1 zinc(II) cyanide 
• 39263-32-6 2-amino-5-bromobenzonitrile 
• 65426-59-7 4-nitrobenzene-1,3-dicarboxylic acid diamide 
• 88678-15-3 4-nitroisophthalic acid dichloride 
• 4315-09-7 4-nitroisophthalic acid 
• 615-57-6 2,4-dibromo-aniline 
• 151-50-8 potassium cyanide 
• 619-72-7 4-nitrobenzonitrile 
• 52054-41-8 4-nitroisophthalonitrile 
• 544-92-3 copper(I) cyanide 

Downstream Products

• 97510-14-0 4-(4-Cyano-phenylamino)-isophthalonitrile 
• 1334331-27-9 2,4-dioxo-1,2,3,4-tetrahydroquinazoline-7-carbonitrile 
• 1269400-62-5 C₁₈H₂₀N₄O₂ 
• 1269142-46-2 C₃₃H₄₄N₄O₇ 
• 1269142-44-0 C₂₈H₃₆N₄O₆ 
• 1269142-40-6 C₁₈H₂₉N₃O₄ 
• 1075253-54-1 C₂₈H₃₁N₇OSSi 
• 74192-47-5 4-amino-3-cyanobenzoic acid 
• 99767-45-0 2-amino-5-cyanobenzoic acid 
• 159847-81-1 methyl 2-AMINO-5-CYANOBENZOATE 
• 159847-80-0 4-amino-3-cyanobenzoic acid methyl ester 

Relevant academic research and scientific papers

Palladium/N-Heterocyclic carbene catalyzed mono- and double-cyanation of aryl halides using potassium ferrocyanide trihydrate under aerobic conditions

Abstract A practical palladium/N-heterocyclic carbene catalyzed procedure for the mono- and double-cyanation of aryl halides is described using inexpensive, easy-to-handle and nontoxic potassium ferrocyanide trihydrate {K4[Fe(CN)6]·3H2O} as the cyanating agent. The reaction does not require an anhydrous solvent, or the exclusion of air or moisture. A variety of electron-rich and electron-deficient aryl halides are efficiently converted into their corresponding nitriles and dicarbonitriles.

Benzoylureas as removable cis amide inducers: Synthesis of cyclic amides via ring closing metathesis (RCM)

Rapid and high yielding synthesis of medium ring lactams was made possible through the use of a benzoylurea auxiliary that serves to stabilize a cisoid amide conformation, facilitating cyclization. The auxiliary is released after activation under the mild conditions required to deprotect a primary amine, such as acidolysis of a Boc group in the examples given here. This methodology is a promising tool for the synthesis of medium ring lactams, macrocyclic natural products and peptides.

Design, structure-activity relationships and in vivo characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: Novel class of receptor tyrosine kinase inhibitors

The inhibition of key receptor tyrosine kinases (RTKs) that are implicated in tumor vasculature formation and maintenance, as well as tumor progression and metastasis, has been a major focus in oncology research over the last several years. Many potent small molecule inhibitors of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases have been evaluated. More recently, compounds that act through the complex inhibition of multiple kinase targets have been reported and may exhibit improved clinical efficacy. We report herein a series of potent, orally efficacious 4-amino- 3-benzimidazol-2-ylhydroquinolin-2-one analogues as inhibitors of VEGF, PDGF, and fibroblast growth factor (FGF) receptor tyrosine kinases. Compounds in this class, such as 5 (TKI258), are reversible ATP- competitive inhibitors of VEGFR-2, FGFR-1, and PDGFRβ with IC50 values 0.1 μM. On the basis of its favorable in vitro and in vivo properties, compound 5 was selected for clinical evaluation and is currently in phase I clinical trials.

Water-induced fluorescence quenching of mono- and dicyanoanilines

Photophysical properties of monocyano- (2-, 3-, and 4-cyano) and dicyano- (3,4-, 3,5-, 2,3-, 2,4-, 2,5-, and 2,6-dicyano) anilines are investigated by fluorescence measurements. All the monocyanoanilines are virtually nonfluorescent in water (quantum yield 0.01); however, in nonaqueous solvents (cyclohexane, acetonitrile and ethanol), the fluorescence quantum yield is enhanced substantially. In contrast, dicyanoanilines investigated are highly fluorescent both in aqueous and nonaqueous environments. The photophysical data and MO calculations suggest that conformational changes in the amino group and variation of hydrogen-bonding interactions between the solute and solvent water upon electronic excitation are responsible for the water quenching in the monocyanoanilines.

Combination therapy with CHK1 inhibitors

Compounds of Structure I, and salts, tautomers, stereoisomers, and mixtures thereof may be used in methods of inhibiting checkpoint kinase 1 in subjects, in methods for inducing cell cycle progression, and in methods for increasing apoptosis in cells. Such compounds may be used to prepare pharmaceutical compositions and may be used in conjunction with DNA damaging agents.

Inhibition of FGFR3 and treatment of multiple myeloma

Methods of inhibiting fibroblast growth factor receptor 3 and treating various conditions mediated by fibroblast growth factor receptor 3 are provided that include administering to a subject a compound of Structure I, a pharmaceutically acceptable salt thereof, a tautomer thereof, or a pharmaceutically acceptable salt of the tautomer. Compounds having the Structure I have the following structure where and have the variables described herein. Such compounds may be used to prepare medicaments for use in inhibiting fibroblast growth factor receptor 3 and for use in treating conditions mediated by fibroblast growth factor receptor 3 such as multiple myeloma.

BENZIMIDAZOLE QUINOLINONES AND USES THEREOF

Methods of inhibiting various enzymes and treating various conditions are provided that include administering to a subject a compound of Structure I or IB, a pharmaceutically acceptable salt thereof, a tautomer thereof, or a pharmaceutically acceptable salt of the tautomer. Compounds having the Structure I and IB have the following structures and have the variables described herein. Such compounds may be used to prepare medicaments for use in inhibiting various enzymes and for use in treating conditions mediated by such enzymes.

3H-azepines and related systems. Part 5. Photo-induced ring expansions of o-azidobenzonitriles to 3-cyano- and 7-cyano-3H-azepin-2(1H)-ones

Unlike other aryl azides bearing electron-withdrawing ortho-substituents, o-azidobenzonitriles on photolysis in aqueous-tetrahydrofuran yield mixtures of the expected 3-cyano- and the unexpected 7-cyano-3H-azepin-2(1H)-ones. In one instance ring contraction to a 2-azabicyclo[3.2.0]hept-6-ene-3-one is noted. X-ray crystallographic data for 7-cyano- and 4-chloro-7-cyano-3H-azepin-2-one, and for the azabicycloheptenone, are presented.

Regioselective Hydrolysis of Aromatic Dinitriles Using a Whole Cell Catalyst

A series of aromatic dinitriles have been examined as substrates for an immobilised whole cell Rhodococcus sp. that catalyses the hydrolysis of nitriles to amides and/or carboxylic acids.The fluorinated aromatic dinitriles 48 and 49 were regioselectively hydrolysed to the corresponding cyano amides 48a and 49a whereas the non-fluorinated analogues 41-44 were converted to cyano acids but with poorer regioselectivity.

Aromatic Nitro-group Displacement Reactions. Part 3. Minor Products of the o-Cyanophenol Synthesis

In dipolar aprotic solvents, the action of cyanide ions on a moderately activated aromatic or heteroaromatic nitro-compound yields, in addition to the o-cyanophenol, a range of products generated through nitro-group reduction.