41283-00-5

Basic information

• Product Name: N²-(4-chlorophenyl)-6-phenyl-1,3,5-triazine-2,4-diamine
• Synonyms: N²-(4-chlorophenyl)-6-phenyl-1,3,5-triazine-2,4-diamine
• CAS NO: 41283-00-5
• Molecular Weight: 297.747
• Mol File: 41283-00-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N²-(4-chlorophenyl)-6-phenyl-1,3,5-triazine-2,4-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: N²-(4-chlorophenyl)-6-phenyl-1,3,5-triazine-2,4-diamine(41283-00-5)
• EPA Substance Registry System: N²-(4-chlorophenyl)-6-phenyl-1,3,5-triazine-2,4-diamine(41283-00-5)

Safety Data

• Hazardous Substances Data: 41283-00-5(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 18915-35-0 1-(4-chloro-phenyl)-6-phenyl-1,6-dihydro-[1,3,5]triazine-2,4-diamine 
• 5304-59-6 4-chlorophenylbiguanide 
• 100-51-6 benzyl alcohol 
• 96730-35-7 1-(4'-chlorophenyl)-2-phenyl-4,6-diamino-1,2-dihydro-1,3,5-triazine hydrochloride 
• 106-47-8 4-chloro-aniline 

Relevant articles and documents

6,: N 2-Diaryl-1,3,5-triazine-2,4-diamines: Synthesis, antiproliferative activity and 3D-QSAR modeling

A library of 126 compounds with a 6,N2-diaryl-1,3,5-triazine-2,4-diamine scaffold was prepared using a one-pot, microwave-assisted method from readily available cyanoguanidine, aromatic aldehydes and arylamines. The three-component condensation of these reagents in the presence of hydrochloric acid was followed by the treatment with a base, which promoted a rearrangement of the dihydrotriazine ring and its dehydrogenative aromatization. The antiproliferative properties of the prepared compounds were evaluated using three breast cancer cell lines. The most promising results were obtained in the growth inhibition of the triple negative MDA-MB231 breast cancer cells. The active compounds were also selective against cancer cells and did not affect growth of the non-cancerous MCF-10A breast cell line. Analyzing the structure-activity relationship within the series, we built a 3D-QSAR model for the further design of more potent anticancer compounds.

New one-pot synthesis of 1,3,5-triazines: three-component condensation, dimroth rearrangement, and dehydrogenative aromatization

A new, effective one-pot synthesis of the 6,N2-diaryl-1,3,5-triazine-2,4-diamines under microwave irradiation was developed. The method involved an initial three-component condensation of cyanoguanidine, aromatic aldehydes, and arylamines in the presence of hydrochloric acid. Without isolation, the resulting 1,6-diaryl-1,6-dihydro-1,3,5-triazine-2,4-diamines were treated with a base to initiate Dimroth rearrangement and spontaneous dehydrogenative aromatization, affording the desired compounds. The developed method was found to be sufficiently general in scope, tolerating various aromatic aldehydes and amines; by using their combinations in the first step, a representative library of 110 compounds was successfully prepared and screened for anticancer properties.