18333-73-8

Upstream product

• 67-56-1 methanol 
• 10199-89-0 NBD chloride 
• 74-89-5 methylamine 

Downstream Products

• 65703-47-1 2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)ethanol 
• 101237-27-8 N-(4-Dimethylaminophenyl)-4-amino-7-nitrobenz-2,1,3-oxadiazol 
• 101237-23-4 N-(2-Hydroxyphenyl)-4-amino-7-nitrobenz-2,1,3-oxadiazol 
• 81432-12-4 (S)-1-(7-Nitro-benzo[1,2,5]oxadiazol-4-yl)-pyrrolidine-2-carboxylic acid 
• 18333-80-7 2-((7-nitrobenzo[c][1,2,5]oxadiazol-4-yl)amino)acetic acid 
• 101321-62-4 4-(2-Methyl-N-piperidyl)-7-nitrobenz-2,1,3-oxadiazol 
• 101237-26-7 N-(4-Aminophenyl)-4-amino-7-nitrobenz-2,1,3-oxadiazol 
• 18378-29-5 4-methylamino-7-nitro-2,1,3-benzoxadiazole 
• 101237-24-5 N-(3-Hydroxyphenyl)-4-amino-7-nitrobenz-2,1,3-oxadiazol 
• 64917-85-7 1-(7-Nitro-4-benzofurazanyl)-L-alanine 
• 18378-15-9 7-nitro-N-phenylbenzo[c][1,2,5]oxadiazol-4-amine 
• 101237-22-3 7-nitro-N-(p-tolyl)benzo[c][1,2,5]oxadiazol-4-amine 
• 101237-25-6 N-(4-Hydroxyphenyl)-4-amino-7-nitrobenz-2,1,3-oxadiazol 

Relevant academic research and scientific papers

Reactions of substituted phenylnitromethane carbanions with aromatic nitro compounds in methanol: Carbanion reactivity, kinetic, and equilibrium studies

The feasibility of carrying out nucleophilic addition from electron-deficient heteroaromatics has been addressed through a detailed investigation of the interaction of a two 7-substituted-nitrobenzofurazan (R = OMe 2a; R = Cl 2b) with a series of substituted-nitroaryl anions (X = 4-NO 2 1a; X = 3-NO2 1b; X = 4-CN 1c; X = 4-Br 1d), all reactions first lead to the quantitative formation of the σ-adducts 3a-d and 4a-d arising from covalent addition of the nucleophile to the C-5 carbon. The rate and equilibrium constants for the formation of σ-adducts 3a-d and 4a-d (k5, K5) together with the rate constants for their decomposition (k-5) have been determined in methanol at 25C, allowing a determination of intrinsic rate constants, k0 = 0.03, the lower k0 value reflects the very strong salvation by methanol of the negative charge on the nitro group. The discovery of a linear correlation between the E and pKaMeOH parameters allows a calibration of the electrophilicity power of 2a and 2b, E = -11.67 and -10.29, respectively. Applying the general approach to nucleophilicity/electrophilicity recently developed by Mayr et al. through the relationship log k = s(E + N), a successful ranking of our nitroaryl anions 1a-d on the general nucleophilicity scale (N) has been carried out. The N values of 1a-d are found to cover a range from 15.78 to 16.69. The results are compared with previously reported data in water and DMSO.

Derivatization of Amines with 4-Substituted 7-Nitrobenzofurazans

Electrophilic derivatives of 4-nitro-benzofurazan with different reactivities were used to synthesize 28 new mono- and disubstituted 4-amino-7-nitrobenzofurazans 2b, 2d, 2f-2i, 2l, 2m-2n, 3b-3f, 3h-3j, 4c-4d, 4f-4k, 4m, 4o-4p.A reaction mechanism is proposed on the basis of the differences of the reactivities and a preliminary kinetic examination.The acid character of the N-H-function in monosubstituted compounds is demonstrated by means of spectroscopical investigation of pKa-values.Data from i.r., u.v./vis, and fluorescence studies are offered.