26242-93-3

Upstream product

• 582-78-5 N-(4-methylphenyl)benzamide 
• 98-88-4 benzoyl chloride 
• 89-62-3 4-methyl-2-nitroaniline 
• 106-49-0 p-toluidine 

Downstream Products

• 122652-20-4 N-(4-methyl-2-nitro-phenyl)-benzimidoyl chloride 
• 325803-76-7 3-nitro-benzoic acid-(4-methyl-2-nitro-anilide) 
• 53476-33-8 2'-amino-4'-methylbenzanilide 
• 65-85-0 benzoic acid 
• 89-62-3 4-methyl-2-nitroaniline 
• 305357-79-3 3-(5-methyl-1H-benzimidazol-2-yl)aniline 
• 351161-82-5 (5-methyl-1H-benzo[d][1,2,3]triazol-1-yl)(phenyl)methanone 
• 2963-65-7 5-methyl-2-phenyl-1H-1,3-benzimidazole 
• 5467-06-1 N,N'-(4-methyl-o-phenylene)-bis-benzamide 
• 313485-85-7 4-methyl-2-phenylazobenzanilide 
• 313485-87-9 6-methyl-1-phenylaminobenzimidazole 
• 313485-86-8 4-methyl-2-phenylazoaniline 

Relevant academic research and scientific papers

Copper-mediated regioselective efficient direct ortho-nitration of anilide derivatives

The mild and readily available Cu(NO3)2 mediated ortho nitration of anilides with broad substrate using K2S2O8 as an oxidant in the absence of any other metal catalyst and nitrating agent under mild conditions was reported for the first time.

Sodium persulfate-promoted site-selective synthesis of mononitroarylamines under transition-metal-free conditions

A practical preparation of nitroarylamines from protected arylamines was herein disclosed. In this system, sodium nitrite acted as a nitration reagent in the presence of sodium persulfate without any transition-metal catalysts. This efficient site-selective protocol took place at room temperature for a short time through a free radical pathway.

Silver-Catalyzed Chemo- and Regioselective Nitration of Anilides

A new and efficient Ag-catalyzed method for the nitration of anilides by using sodium nitrite as a cheap and available NO2 source has been developed. This C–H functionalization reaction is ortho-selective, achieves moderate to high yields and shows excellent functional group tolerance. Furthermore, it provides a novel approach to ortho-nitrated anilides, which are very tricky to access with traditional methods.

Copper-Catalyzed Direct Nitration on Aryl C-H Bonds by Concomitant Azidation-Oxidation with TMS Azide and TBHP under Aerobic Conditions

An unprecedented copper-catalyzed in situ azidation-oxidation for the nitration of anilides and sulfonamides has been developed by direct CAr-H functionalization. This novel and efficient nitration protocol is achieved employing TMSN3 and TBHP without the exclusion of air or moisture. The synthetic applications of the 2-nitroanilides have been explored.

Copper-catalyzed mild nitration of protected anilines

A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.

Syntheses and properties of 1-methyl-3-phenylaminobenzimidazolium salts, models of DNA adducts of N7-arylaminodeoxyguanosinium salt

When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Heating compound 7 at 80 °C for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N1-formyl-N1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazoles, the 3-phenylamino derivative was found to be more reactive.