939-83-3

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-5-NITROBENZONITRILE is used as a key intermediate in the synthesis of 5-(2-methyl-5-nitrophenyl)-1H-tetrazole, which is a heterocyclic compound with potential pharmaceutical applications. The tetrazole ring is a common structural motif in many bioactive molecules, and its incorporation into drug candidates can enhance their pharmacological properties.
Used in Chemical Industry:
2-METHYL-5-NITROBENZONITRILE can also be used as a building block in the synthesis of various organic compounds, such as dyes, pigments, and polymers. Its reactivity and functional groups make it a versatile starting material for the preparation of a wide range of chemical products.

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 4971, 1984 DOI: 10.1016/S0040-4039(01)91273-0

InChI:InChI=1/C8H6N2O2/c1-6-2-3-8(10(11)12)4-7(6)5-9/h2-4H,1H3

Upstream product

• 529-19-1 2-Methylbenzonitrile 
• 7745-93-9 2-bromo-4-nitrotoluene 
• 105-56-6 ethyl 2-cyanoacetate 
• 7745-92-8 2-iodo-1-methyl-4-nitrobenzene 
• 557-21-1 dicyanozinc 

Downstream Products

• 61599-49-3 2-cyano-4-nitrostilbene 
• 61599-50-6 4-nitro-trans-stilbene-carboxylic acid-⁽²⁾-amide 
• 61599-51-7 4'-hydroxy-4-nitro-stilbene-2-carbonitrile 
• 61599-52-8 2-cyano-4'-methoxy-4-nitrostilbene 
• 106987-30-8 2',4'-dimethoxy-4-nitro-stilbene-2-carbonitrile 
• 2695-76-3 1,3-Bis-(2-Cyan-4-nitro-trans-styryl)-benzol 
• 2695-75-2 3'-Formyl-4-nitro-trans-stilben-2-carbonitril 
• 2695-71-8 1,4-Bis-(2-Cyan-4-nitro-trans-styryl)-benzol 
• 2695-70-7 4'-Formyl-4-nitro-trans-stilben-2-carbonitril 
• 109386-33-6 2-carbethoxy-12-(2'-cyano-4'-nitrophenyl)-naphth<2,3-b>indolizine-6,11-dione 
• 109386-36-9 2-amino-12-(2'-cyano-4'-nitrophenyl)naphth<2,3-b>indolizine-6,11-dione 
• 109386-47-2 14-(2'-cyano-4'-nitrophenyl)benzonaphth<2,3-b>indolizine-8,13-dione 
• 109386-35-8 2-acetamido-12-(2'-cyano-4'-nitrophenyl)naphth<2,3-b>indolizine-6,11-dione 
• 6615-56-1 2-[(E)-2-(4-Chloro-phenyl)-vinyl]-5-nitro-benzonitrile 

Relevant academic research and scientific papers

Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS): An efficient catalyst for cyanation reaction in aqueous media

Immobilized palladium nanoparticles on a cyclodextrin-polyurethane nanosponge (Pd-CD-PU-NS) were found to be an efficient heterogeneous catalyst in the cyanation reaction of aryl halides in aqueous media. This catalyst system is containing palladium nanoparticles with a size of ～7 nm. Moreover, the CD-PU-NS support formed microsphere-shaped structures with a size of ～100–200 nm. The TEM images show that Pd nanoparticles were formed in near spherical shape morphology and were immobilized in the structure of the CD-PU-NS support. Under our optimized reaction conditions, aryl cyanides were obtained in high yields in the presence of the Pd-CD-PU-NS catalyst. Our results demonstrated that the Pd-CD-PU-NS catalyst is highly effective in the cyanation reaction in aqueous media. Furthermore, the catalyst could be simply extracted from the reaction mixture, providing an efficient methodology for the synthesis of aryl cyanides. The Pd-CD-PU-NS catalyst could be recycled four times with almost consistent catalytic efficiency.

Ethyl cyanoacetate: A new cyanating agent for the palladium-catalyzed cyanation of aryl halides

A new Pd-catalyzed cyanation reaction has been discovered using ethyl cyanoacetate as the cyanating reagent. A variety of electron-rich and electron-deficient aryl halides were efficiently converted into their corresponding nitriles in good to excellent yields.

Highly efficient triarylene conjugated dyes for sensitized solar cells

A new series of organic dyes containing a triarylamine donor group, a triarylene-linked bridging moiety, and a cyanoacrylic acid acceptor group were synthesized through a simple procedure in high yields. A selected set of substituents were added onto the

Dihydroxylphenyl amides as inhibitors of the Hsp90 molecular chaperone

Information from X-ray crystal structures were used to optimize the potency of a HTS hit in a Hsp90 competitive binding assay. A class of novel and potent small molecule Hsp90 inhibitors were thereby identified. Enantio-pure compounds 31 and 33 were potent in PGA-based competitive binding assay and inhibited proliferation of various human cancer cell lines in vitro, with IC50 values averaging 20 nM.

AMIDE RESORCINOL COMPOUNDS

The present invention is directed to compounds of formula (I), and pharmaceutically acceptable salts and solvates thereof, their synthesis, and their use as HSP-90 inhibitors.

Nitration of moderately deactivated arenes with nitrogen dioxide and molecular oxygen under neutral conditions. Zeolite-induced enhancement of regioselectivity and reversal of isomer ratios

In the presence of zeolites, moderately deactivated arenes such as 1-nitronaphthalene, naphthonitriles, and methylated benzonitriles can be smoothly nitrated at room temperature by the combined action of nitrogen dioxide and molecular oxygen. The regioselectivity is considerably improved as compared with the conventional nitration methodology based on nitric and sulfuric acids. In some cases, the minor isomer became favoured to a significant extent, resulting in the reversal of ordinary isomer ratios of nitration products.

SUBSTITUTED THIAZOLE DERIVATIVES BEARING 3-PYRIDYL GROUPS, PROCESS FOR PREPARING THE SAME AND USE THEREOF

The present invention provides a pharmaceutical composition having a steroid C17,20-lyase inhibitory activity, which is useful as a prophylactic or therapeutic agent of prostatism, tumor such as breast cancer and the like, more particularly, a steroid C17,20-lyase inhibitor containing a compound represented by the formula: wherein A1 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, one of A2 and A3 is a hydrogen atom, a halogen atom, a C1-4 aliphatic hydrocarbon group optionally having substituents or an optionally esterified carboxyl group, the other of A2 and A3 is an aromatic hydrocarbon group optionally having substituents or a heterocyclic group optionally having substituents, and at least one of A1, A2 and A3 is a 3-pyridyl group optionally having substituents, or a salt thereof or a prodrug thereof.

Synthesis and spectroscopic properties of finite Ph 2N-containing oligo(arylenevinylene) derivatives that emit blue to red fluorescence

(Matrix presented) A series of oligo(phenylenevinylene) (OPV) derivatives with finite conjugation units were prepared in short steps from few building blocks. The central and terminal aryl groups of these OPV dyes contain cyano and Ph2N substituents, respectively, which affect color of fluorescence. The wavelength ranges from 472 nm (blue) to 614 nm (red) depending on the position of the cyano group.

A novel method for the nitration of deactivated aromatic compounds

Novel nitration systems comprising nitric acid, trifluoroacetic anhydride and zeolite Hβ, with or without acetic anhydride, are described. The system having no acetic anhydride is more active and readily nitrates deactivated substrates such as nitrobenzene, benzonitrile, benzoic acid or 4-nitrotoluene to give predominantly the product substituted meta to the deactivating group. The system incorporating acetic anhydride is more moderate in activity, and nitrates moderately deactivated systems such as halogenobenzenes quantitatively within two hours at ice-salt bath temperature, and provides very high selectivity for the para-nitrated product. This system also nitrates 2-nitrotoluene to give high selectivity for 2,4-dinitrotoluene production. Furthermore, the system can be used for direct double nitration of toluene and gives a 92% yield of 2,4-dinitrotoluene with a 2,4- : 2,6-dinitrotoluene ratio of 25:1. Even greater selectivity (96% yield and 70:1 selectivity) can be achieved in the latter reaction by conducting the reaction in one flask but in two stages, with trifluoroacetic anhydride added only in the second stage. The Royal Society of Chemistry 2000.