1527-91-9

Usage

Uses

Used in Organic Synthesis:
N-Phenylbenzamidine is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the formation of complex organic molecules.
Used in Research and Medical Laboratories:
N-Phenylbenzamidine is used as an inhibitor of trypsin-like serine proteases and the enzyme thrombin, making it valuable in research for understanding enzyme functions and in medical laboratories for its anticoagulant properties.
Used in Pharmaceutical Development:
Due to its ability to inhibit thrombin, N-Phenylbenzamidine is utilized in the development of pharmaceuticals aimed at preventing blood clot formation, which is crucial in the treatment and management of various cardiovascular conditions.
Used in Diagnostic Applications:
In diagnostic settings, N-Phenylbenzamidine may be employed to study the activity of serine proteases, which are involved in numerous physiological processes and can be indicators of certain diseases when their activity is abnormal.
Used in Industrial Chemical Processes:
N-Phenylbenzamidine's properties as a reagent and inhibitor make it suitable for use in various industrial chemical processes where specific enzymatic activities need to be controlled or modulated.

InChI:InChI=1/C13H12N2/c14-13(11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15)/p+1

Upstream product

• 93-98-1 N-phenyl benzoyl amide 
• 2556-46-9 N,N'-diphenylbenzamidine 
• 19402-64-3 ammonium benzenesulfonate 
• 614-28-8 N-benzoylbenzamide 
• 142-04-1 aniline hydrochloride 
• 3488-57-1 N-phenylbenzamidoxime 
• 4484-20-2 aniline benzenesulfonate 
• 100-47-0 benzonitrile 
• 62-53-3 aniline 
• 4903-36-0 N-phenyl-benzimidoyl chloride 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 2227-79-4 benzenecarbothioamide 
• 16776-73-1 N-benzoyl-benzamidine 
• 622-34-4 1-phenylcyanamide 

Downstream Products

• 33048-82-7 N-benzoyl-N-phenyl-benzamidine 
• 22668-43-5 N,N′-dibenzoyl-N-phenylbenzamidine 
• 82208-28-4 N-benzoyl-N'-phenyl-benzamidine 
• 33655-23-1 N¹-(N-Phenylcarbamoyl)-N²-phenylbenzimidamide 
• 20800-34-4 N-(N-Phenyl-benzimidoyl)-N'-phenyl-thioharnstoff 
• 27142-44-5 N²,N⁴-diphenylquinazoline-2,4-diamine 
• 25225-73-4 6-chloro-2-phenyl-4H-benzo[e][1,3]oxazin-4-one 
• 872294-83-2 N-(α-anilino-benzylidene)-N'-phenyl-benzamidine 
• 2556-46-9 N,N'-diphenylbenzamidine 
• 33345-17-4 N,N-diphenylbenzamidine 
• 13136-18-0 N',N''-diphenylbenzimidohydrazide 
• 56844-87-2 N,N'-dimethyl-N-phenyl-benzamidine 
• 57767-07-4 N-methyl-N-phenylbenzimidamide 
• 3488-57-1 N-phenylbenzamidoxime 

Relevant academic research and scientific papers

Synthesis of 1,2,4,5-tetrasubstituted imidazoles and 2,4,5,6-tetrasubstituted pyrimidines: three-component, the one-pot reaction of arylamidines, malononitrile, and arylglyoxals or aryl aldehydes

A highly efficient one-pot synthesis of the 1,2,4,5-tetrasubstituted imidazoles and 2,4,5,6-tetrasubstituted pyrimidines through an arylamidine, malononitrile, and carbonyl compound by using Et3N in CH3CN at reflux conditions was dev

Phosphorescent Cyclometalated Platinum(II) aNHC Complexes

The synthesis and characterization of the first bidentate C^C* cyclometalated platinum(II) complexes based on abnormal N-heterocyclic carbenes (aNHC) is presented. The aNHC ligand precursors are prepared from benzonitriles and anilines to form 1,2,3-trisu

Combination of air/moisture/ambient temperature compatible organolithium chemistry with sustainable solvents: Selective and efficient synthesis of guanidines and amidines

Highly-efficient and selective fast addition of in situ generated lithium amides [LiN(H)R] (obtained via an acid-base reaction between n-BuLi and the desired primary amine) into carbodiimides (R-NCN-R) or nitriles (R-CN) has been studied, for the first ti

Photoredox synthesis of functionalized quinazolinesviacopper-catalyzed aerobic oxidative Csp2-H annulation of amidines with terminal alkynes

We have developed a visible light-induced photo-redox copper-catalyzed oxidative Csp2-H annulation (Friedel-Crafts-type cyclization) of amidines with terminal alkynes at room temperature to synthesize functionalized quinazolines. We report copp

Synthesis of aminoisoquinolines via Rh-catalyzed [4 + 2] annulation of benzamidamides with vinylene carbonate

A new strategy is developed for the synthesis of 1-aminoisoquinoline derivatives. This Rh(III)-catalyzed [4 + 2] annulation reaction employs benzamidines as efficient directing groups and the vinylene carbonate as an acetylene surrogate. Additionally, the reaction features broad substrate scopes and good yields, only producing carbonate anion as byproduct.

Construction of a novel asymmetric imidazole-cored AIE probe for ratiometric imaging of endogenous leucine aminopeptidase

We report a rational strategy to deliberately construct the first asymmetric tetraarylimidazole-based AIE probe, integrating AIE behavior in synergy with ESIPT character to image endogenous LAP for the first time. It offered good sensitivity and selectivity, and concomitantly, was applied successfully for real-time tracking of LAP in the cisplatin-induced liver injury zebrafish model.

Direct, Late-Stage Mono-N-arylation of Pentamidine: Method Development, Mechanistic Insight, and Expedient Access to Novel Antiparastitics against Diamidine-Resistant Parasites

A selective mono-N-arylation strategy of amidines under Chan-Lam conditions is described. During the reaction optimization phase, the isolation of a mononuclear Cu(II) complex provided unique mechanistic insight into the operation of Chan-Lam mono-N-arylation. The scope of the process is demonstrated, and then applied to access the first mono-N-arylated analogues of pentamidine. Sub-micromolar activity against kinetoplastid parasites was observed for several analogues with no cross-resistance in pentamidine and diminazene-resistant trypanosome strains and against Leishmania mexicana. A fluorescent mono-N-arylated pentamidine analogue revealed rapid cellular uptake, accumulating in parasite nuclei and the kinetoplasts. The DNA binding capability of the mono-N-arylated pentamidine series was confirmed by UV-melt measurements using AT-rich DNA. This work highlights the potential to use Chan-Lam mono-N-arylation to develop therapeutic leads against diamidine-resistant trypanosomiasis and leishmaniasis.

Intramolecular hydrogen bonding stabilizes trans-configuration in a mixed carbene/isocyanide PdII complexes

Aromatic amidines 1a-e undergo facile reaction with one isocyanide in PdCl2(CNBut)2 giving carbene complexes 2b-d (Scheme 2) in high isolated yields (79–95%). The structures of 2b–d were confirmed by the 1H and

Base-mediated cascade amidination/: N -alkylation of amines by alcohols

A base-mediated cascade amidination/N-alkylation reaction of amines by alcohols has been developed. For the first time, nitriles have been identified as an efficient and benign water acceptor reagent in N-alkylation. Notably, the procedure tolerates a series of functional groups, such as methoxyl, halo, vinyl and hetero groups, providing a convenient method to construct different substituted diamino compounds, 15N labeled amine and could be scaled up to 1 mol scale offering 138.7 g of the desired product in good yield in one-pot. Mechanistic studies provided strong evidence for the amidination of amines with nitriles facilitated by t-BuOK.

Transition-Metal-Free Synthesis of 1,2-diphenyl-1H-benzo[d] Imidazole Derivatives from N-phenylbenzimidamides and Cyclohexanones

A transition-metal-free strategy for the formation of 1,2-diphenyl-1H-benzo[d] imidazoles from N-phenylbenzimidamides and cyclohexanones is introduced. This is the first report on the direct synthesis of 1,2-diphenyl-1H-benzo[d] imidazoles from cyclohexanones and N-phenylbenzimidamides via iodine- promoted oxidative cyclization. Non-aromatic cyclohexanones were smoothly dehydrogenated, and acted as an aryl source using oxygen as a green oxidant. The catalytic use of iodine makes this method quite simple, more economical and convenient. Under optimized conditions, various substituted 1,2-diphenyl-1H-benzo[d] imidazoles were smoothly reacted, and the desired substituted imidazoles were generated with moderate to excellent yields. (Figure presented.).