33490-01-6

Upstream product

• 122-04-3 4-nitro-benzoyl chloride 
• 88-74-4 2-nitro-aniline 
• 1429-05-6 phenyl 4-nitrobenzoate 
• 5466-94-4 4-Nitro-N-phenyl-benzimidoyl chloride 
• 38430-14-7 N-Phenyl-4-nitro-benzimid-saeurechlorid 
• 15163-59-4 potassium o-nitrobenzoate 
• 619-80-7 4-nitrobenzamide 

Downstream Products

• 2963-77-1 4-(1H-benzimidazol-2-yl)aniline 
• 99137-11-8 4-nitro-N-(2-nitro-phenyl)-benzimidoyl chloride 
• 27030-98-4 N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)ethanamide 
• 98806-50-9 N-(4-(1H-benzo[d]imidazol-2-yl)phenyl)benzamide 
• 99137-17-4 1-(2-nitrophenyl)-5-(4-nitrophenyl)tetrazole 
• 67236-55-9 4-nitro-2-(4-nitrophenyl)benzimidazole 
• 51776-70-6 2-(4-nitrophenyl)-2H-benzo[d][1,2,3]triazole 
• 37632-91-0 2',4',4-trinitrobenzanilide 
• 89844-36-0 2',6',4-trinitrobenzanilide 

Relevant academic research and scientific papers

Colorimetric detection of cyanide with N-nitrophenyl benzamide derivatives

A series of structurally simple N-nitrophenyl benzamide derivatives have been developed as chemosensors toward cyanide in aqueous environment by taking advantage of the cyanide's strong affinity toward the acyl carbonyl carbon. The high selectivity of these compounds toward CN- makes it a practical system for monitoring CN- concentrations in aqueous samples.

Biological evaluation and molecular docking studies of nitro benzamide derivatives with respect to in vitro anti-inflammatory activity

A series of nitro substituted benzamide derivatives were synthesized and evaluated for their potential anti-inflammatory activities in vitro. Firstly, all compounds (1–6) were screened for their inhibitory capacity on LPS induced nitric oxide (NO) production in RAW264.7 macrophages. Compounds 5 and 6 demonstrated significantly high inhibition capacities in a dose-dependent manner with IC50 values of 3.7 and 5.3 μM, respectively. These two compounds were also accompanied by no cytotoxicity at the studied concentrations (max 50 μM) in macrophages. Molecular docking analysis on iNOS revealed that compounds 5 and 6 bind to the enzyme more efficiently compared to other compounds due to having optimum number of nitro groups, orientations and polarizabilities. In addition, 5 and 6 demonstrated distinct regulatory mechanisms for the expression of the iNOS enzyme at the mRNA and protein levels. Specifically, both suppressed expressions of COX-2, IL-1β and TNF-α significantly, at 10 and 20 μM. However, only compound 6 significantly and considerably decreased LPS-induced secretion of IL-1β and TNF-α. These results suggest that compound 6 may be a multi-potent promising lead compound for further optimization in structure and as well as for in vivo validation studies.

CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines

CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently

Reaction of N-Aryl- and N-Alkyl-benzimidoyl Chlorides with Silver Nitrate

N-Arylbenzimidoyl chlorides, in which the N-aryl group is unsubstituted at the ortho- and para-positions, react with AgNO3 to yield N-(nitroaryl)benzamides, in which the NO2 group resides in the ortho- or para-position.N-Arylbenzimidoyl chlorides, in which the N-aryl ring is 2,4,6-trisubstituted, react with AgNO3 to yield the corresponding N-aryl-N-nitrobenzamides.The formation of both types of product can be explained by the intermediacy of an O-nitro imidate.Spectroscopic and chemical evidence is presented for the formation of this intermediate in the reaction of N-(2,4,6-trisubstituted phenyl)benzimidoyl chlorides with AgNO3.Rearrangement of the O-nitro imidate is unimolecular and intramolecular.The rate of rearrangement is independent of the substituent in the C-aryl ring, but increases with the electon-withdrawing ability of the substituents in the N-aryl ring.A mechanism is proposed in which the imidoyl chloride reacts with AgNO3 to produce first a nitrilium ion which goes on to form an O-nitro imidate that subsequently rearranges via a homolytic cleavage of the O-NO2 bond.The ortho:para ratios of N-(nitroaryl)benzamides obtained in the present work indicate that O-nitro imidates are not responsible for the high 1/2ortho:para ratios sometimes observed in the nitration of anilides.N-Alkylbenzimidoyl chlorides react with AgNO3 to form the corresponding N-nitro- and N-nitrosobenzamides.The mechanism of formation of the N-alkyl-N-nitrobenzamide arises from a pathway analogous to that for N-aryl-N-nitrobenzamides, involving a nitrilium ion that gives rise to an O-nitro imidate.The evidence for the formation of the N-nitrosobenzamide points to an alternative reaction of the imidoyl chloride with AgNO3.One possible mechanism for this reaction is described.

Rearrangement of Imidoyl Nitrates to N-Nitro Amides: an Intramolecular O-to-N Migration of a Nitro Group

Imidoyl nitrates, formed by the reaction of imidoyl chlorides with AgNO3, rearrange via a unimolecular, intramolecular mechanism probably involving homolytic fission of the O-N bond to yield N-nitro amides; migration of the nitro group in N-arylimidoyl nitrates to the ortho- and para-positions of the N-aryl ring does not involve a special ortho-directing effect.