99841-06-2

Basic information

• Product Name: N¹-Salicyloylpiperazine
• CAS NO: 99841-06-2
• Molecular Weight: 206.244
• Mol File: 99841-06-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N¹-Salicyloylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: N¹-Salicyloylpiperazine(99841-06-2)
• EPA Substance Registry System: N¹-Salicyloylpiperazine(99841-06-2)

Safety Data

• Hazardous Substances Data: 99841-06-2(Hazardous Substances Data)

Upstream product

• 110-85-0 piperazine 
• 61141-14-8 anionic phenyl salicylate 
• 118-55-8 phenyl Salicylate 
• 69-72-7 salicylic acid 

Downstream Products

• 151824-78-1 5-(4-Salicyloylpiperazin-1-yl)-1,2-phenylenediamine 
• 151824-81-6 5-(4-Salicyloylpiperazin-1-yl)-2-nitroaniline 

Relevant articles and documents

Effects of mixed H2O-CH3CN solvents on the Bronsted coefficient for the intramolecular general base-catalyzed cleavage of ionized phenyl salicylate in the presence of primary and secondary amines

Nucleophilic second-order rate constants, knms, for the reactions of several primary and secondary amines with ionized phenyl salicylate (PS-) show a nonlinear decrease with the increase in the content of CH3CN from 2 to ≤50% v/v in mixed aqueous solvent. The values of knms remain almost unchanged with the change in the content of CH3CN at >50% v/v. The nucleophilic reactivity of primary and secondary amines toward PS- reveal Bronsted plots of different Bronsted coefficients, βnuc, at a constant content of CH3CN in mixed aqueous solvents. The values of βnuc decrease from 0.4 to nearly 0 for primary amines and from 0.22 to 0.12 for secondary amines with the increase in CH3CN content from 2 to 70% v/v. The values of knms/kMeOHms (where kMeOHms represents the nucleophilic second-order rate constant for the reaction of MeOH with PS- in H2O-CH3CN solvents), obtained within 2-50% v/v CH3CN, fit to an empirical equation: log (knms/kMeOHms) = θ+λX where X is the % v/v content of CH3CN, and θ and λ are empirical constants. It has been shown empirically that both θ and λ are the function of Bronsted coefficient βlg. The values of λ are used to calculate βlg and these βlg values for all amines except Tris lie within -0.32 to -0.46. The effects of mixed water-acetonitrile solvents on pKa of leaving the group, phenol, and conjugate acid of amine nucleophile have been concluded to be the major source for the observed solvent effects on knms. The βlg for Tris is unusually very close to zero.

Synthesis and potential anthelmintic activity of methyl-5-(4-salicyloyl-piperazin-1-yl)-benzimidazole-2-carbamates

A series of methyl-5-(4-salicyloyl-piperazin-1-yl)-benzimidazole-2-carbamates (IX) has been prepared. 5-(4-salicyloyl-piperazin-1-yl)-2-nitro anilines (VII) have been synthesized starting from 5-piperazino-2-nitro anilines and salicyloyl chlorides. Catalytic reduction of VII with Pd/C, followed by treatment with 1,3-dicarbomethoxy-S-methyl isothiourea, yielded the corresponding carbamates (IX), the anthelmintic activity of which was studied. Compound IX(a) significantly reduced the numbers of preadults, adults and encysted T. spiralis larvae in experimental mice.