2863-98-1

Usage

Uses

Used in Organic Synthesis:
4-Cyanophenylhydrazine hydrochloride is used as a synthetic intermediate for the production of various organic compounds. Its application in this field is due to its unique chemical properties, which allow it to participate in a range of chemical reactions, facilitating the synthesis of diverse organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Cyanophenylhydrazine hydrochloride is used as a building block for the development of new drugs. Its ability to undergo various chemical reactions makes it a versatile component in the design and synthesis of pharmaceutical compounds, potentially leading to the creation of novel therapeutic agents.
Used in Chemical Research:
4-Cyanophenylhydrazine hydrochloride is also employed in chemical research as a reagent for studying the properties and behavior of different chemical systems. Its unique structure and reactivity make it an interesting subject for researchers, who can use it to gain insights into various aspects of organic chemistry.
Used in Dye and Pigment Industry:
In the dye and pigment industry, 4-Cyanophenylhydrazine hydrochloride is used as a starting material for the synthesis of various dyes and pigments. Its chemical properties allow it to be transformed into a range of colored compounds, which can be used to produce vibrant and stable dyes and pigments for various applications.

InChI:InChI=1/C7H7N3.ClH/c8-5-6-1-3-7(10-9)4-2-6;/h1-4,10H,9H2;1H

Upstream product

• 873-74-5 4-Aminobenzonitrile 
• 33348-34-4 4-amino-3-iodobenzonitrile 
• 3058-39-7 4-iodobenzonitrile 
• 25102-85-6 p-cyanobenzenediazonium chloride 
• 623-00-7 4-bromobenzenecarbonitrile 
• 623-03-0 4-Cyanochlorobenzene 

Downstream Products

• 128102-58-9 4-{[phenyl-(5-phenyl-[1,2,4]oxadiazol-3-yl)-methylene]-hydrazino}-benzonitrile 
• 101831-71-4 3-(2-aminoethyl)-5-cyano-1H-indole hydrochloride 
• 628294-80-4 7-cyano-1,2,3,4-tetrahydrocyclopent[b]indole 
• 700806-01-5 4-[5-amino-3-(3,4-dimethoxy-phenylamino)-[1,2,4]triazol-1-yl]-benzonitrile 
• 338959-36-7 Ethyl 1-(4-cyanophenyl)-5-methylpyrazole-4-carboxylate 
• 690248-00-1 N¹-(4-cyanophenylmethyl)-N¹-(4-cyanophenyl)hydrazine 
• 827316-54-1 4-{(2E)-2-[1-(1H-pyrazol-3-yl)ethylidene]hydrazino}benzonitrile 
• 897660-90-1 (+/-)-6-cyano-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid methyl-phenyl-amide 
• 524699-77-2 2,2,2-trifluoro-N'-(4-cyanophenyl)ethanehydrazonamide 
• 160133-36-8 2-acetyl-1-(4-cyanophenyl)hydrazine 
• 330803-95-7 ethyl 3-methyl-1-(4-cyanophenyl)-1H-pyrazole-5-carboxylate 
• 1019995-28-8 4-[2-(2-oxo-1,2,3,4-tetrahydro-5H-pyrido[4,3-b]azepin-5-ylidene)hydrazino]benzonitrile 
• 1019995-23-3 4-[2-(2-bromo-6-oxo-5,6,7,8-tetrahydro-9H-pyrido[3,2-b]azepine-9-ylidene)hydrazino]benzonitrile 

Relevant academic research and scientific papers

An investigation of the synthesis of vilazodone

A novel synthetic route toward vilazodone is described by using 4-cyanoaniline and 5-bromo-2-hydroxybenzaldehyde as starting materials, with an overall yield of 24% and 99% purity. First, the intermediate (3-(4-chlorobutyl)-1H-indole-5-carbonitrile) is synthesized via diazotization of 4-cyanoaniline, followed by Fischer indole cyclization with 6-chlorohexanal. Subsequently, another intermediate, 5-(piperazin-1-yl)benzofuran-2-carboxamide, is generated via aromatic nucleophilic substitution of 5-bromobenzofuran-2-carboxamide with piperazine. Finally, vilazodone is obtained via nucleophilic substitution of the above two key intermediates by treatment with Et3N/K2CO3. In comparison to the original process, this route avoids the use of expensive and toxic reagents and resolves issues such as safety, environmental concerns, and high costs.

Continuous flow synthesis of arylhydrazines: via nickel/photoredox coupling of tert -butyl carbazate with aryl halides

Nickel/photoredox catalyzed C-N couplings of hydrazine-derived nucleophiles provide a powerful alternative to Pd-catalyzed methods. This continuous-flow photochemical protocol, optimized using design of experiments, achieves these couplings in short residence times, with high selectivity. A range of (hetero)aryl bromides and chlorides are compatible and understanding of process stability/reactor fouling has been discerned. This journal is

Discovery of 1,3,4-oxadiazol-2-one-containing benzamide derivatives targeting FtsZ as highly potent agents of killing a variety of MDR bacteria strains

The spread of infections caused by multidrug-resistant (MDR) pathogens, such as methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant S. aureus (VRSA), has created a need for new antibiotics with novel mechanisms of action. The bacterial division protein FtsZ has been identified as a novel drug target that can be exploited clinically. As part of an ongoing effort to develop FtsZ-targeting antibacterial agents, we describe herein the design, synthesis and bioactivity of six series of novel 1,3,4-oxadiazol-2-one-containing, 1,2,4-triazol-3-one-containing and pyrazolin-5-one-containing benzamide derivatives. Among them, compound A14 was found to be the most potent antibacterial agent, much better than clinical drugs such as ciprofloxacin, linezolid and erythromycin against all the tested gram-positive strains, particularly methicillin-resistant, penicillin-resistant and clinical isolated S. aureus. Subsequent studies on biological activities and docking analyses proved that A14 functioned as an effective compound targeting FtsZ. Preliminary SAR indicated a general direction for further optimization of these novel analogues. Taken together, this research provides a promising chemotype for developing newer FtsZ-targeting bactericidal agents.

Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4-Oxadiazin-5(6H)-one Derivatives from Dehydroabietic Acid

A series of new 1,3,4-oxadiazin-5(6H)-one derivatives (6a–n) of dehydroabietic acid were designed and synthesized as potential antimicrobial and antitumor agents. Their structures were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analyses. All the title compounds were evaluated for their antimicrobial activity against four bacterial and three fungal strains using the serial dilution method. Among them, compound 6e showed the highest antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) value of 1.9 μg/mL. In addition, the in vitro cytotoxic activities of the title compounds were also assayed against three human carcinoma cell lines (MCF-7, SMMC-7721, and HeLa) through the MTT colorimetric method. As a result, compounds 6b, 6g, 6k, and 6m exhibited significant inhibition against at least one cell line with IC50 values below 10 μM. Compound 6m was especially found to be the most potent derivative with IC50 values of 2.26 ± 0.23, 0.97 ± 0.11, and 1.89 ± 0.31 μM against MCF-7, SMMC-7721, and HeLa cells, respectively, comparable to positive control etoposide.

Synthesis of Aryl Hydrazines via CuI/BMPO Catalyzed Cross-Coupling of Aryl Halides with Hydrazine Hydrate in Water

The N,N’-bis(2,6-dimethylphenyl)oxalamide was discovered as a powerful ligand for Cu-catalyzed cross-coupling of aryl halides with hydrazine hydrate, leading to the formation of a variety of aryl hydrazines at 80 oC in water under the assistance of K3PO4 and 4 mol% cetyltrimethylammonium bromide from aryl bromides and aryl iodides. Good to excellent yields were observed in most cases.

High-Spin Organic Diradical with Robust Stability

Triplet ground-state organic molecules are interesting with respect to several emerging technologies but typically exhibit limited stability. We report two organic diradicals, one of which possesses a triplet ground state (2J/kB = 234 ± 36 K) and robust stability at elevated temperatures. We are able to sublime this high-spin diradical under high vacuum at 140 °C with no significant decomposition.

Alternative approach to synthesis of 3-(4-Chloro butyl)- 1H -indole-5-carbonitrile: A key intermediate of vilazodone hydrochloride, an antidepressant drug

An alternative and efficient telescopic approach to the synthesis of 3-(4-chloro butyl)-1H-indole -5-carbonitrile (2), a key intermediate in the synthesis of vilazodone hydrochloride (1), is described.

Design, synthesis, crystal structures, and insecticidal activities of eight-membered azabridge neonicotinoid analogues

Three series of novel azabridge neonicotinoid analogues were designed and synthesized, which were constructed by starting material A, glutaraldehyde, and primary amine hydrochlorides (aliphatic amines, phenylhydrazines, and anilines). Most of the eight-membered azabridge compounds presented higher insecticidal activities than oxabridged compound B against cowpea aphid (Aphis craccivora) and brown planthopper (Nilaparvata lugens). Compared with imidacloprid, some azabridged compounds exhibited excellent insecticidal activity against brown planthopper. The crystal structures and bioassay indicated that changing bridge atoms from O to N could lead to entirely different conformations, which might be the important influential factor of the bioactivities.

Synthesis of novel celecoxib analogues by bioisosteric replacement of sulfonamide as potent anti-inflammatory agents and cyclooxygenase inhibitors

Two series of celecoxib analogues having 1,5-diaryl relationship were synthesized. The key strategy of the molecular design was oriented towards exploring bioisosteric modifications of the sulfonamide moiety of celecoxib. First series (2a-2i) of celecoxib

Indole synthesis by rhodium(III)-catalyzed hydrazine-directed C-H activation: Redox-neutral and traceless by N-N bond cleavage

Fishing for complements! There is an alternative to the useful Fischer indole synthesis. The new method utilizes the same retrosynthetic disconnection but is based on a RhIII-catalyzed directed C-H activation step and a successive coupling with alkynes. Copyright