132685-68-8

Basic information

• Product Name: Hydrazinecarboximidamide, 2-[(4-chlorophenyl)methylene]-, (2E)-
• CAS NO: 132685-68-8
• Molecular Formula: C8H9ClN4
• Molecular Weight: 196.639
• Mol File: 132685-68-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Hydrazinecarboximidamide, 2-[(4-chlorophenyl)methylene]-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Hydrazinecarboximidamide, 2-[(4-chlorophenyl)methylene]-, (2E)-(132685-68-8)
• EPA Substance Registry System: Hydrazinecarboximidamide, 2-[(4-chlorophenyl)methylene]-, (2E)-(132685-68-8)

Safety Data

• Hazardous Substances Data: 132685-68-8(Hazardous Substances Data)

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 1937-19-5 1-aminoguanidine hydrochloride 
• 2582-30-1 aminoguanidine bicarbonate 

Downstream Products

• 736177-19-8 1-(4-chlorobenzylideneamino)-4-(5-chlorothiophen-2-yl)-1H-imidazol-2-amine 
• 677737-58-5 (E)-N¹-[(4-chlorophenyl)methylene]-4-phenyl-1H-imidazole-1,2-diamine 
• 132901-76-9 C₁₀H₉ClN₆ 

Relevant articles and documents

An unprecedented intramolecular to intermolecular mechanistic switch in 1,1-diaminoazines leading to differential product formation during the I2-induced tandem oxidative transformation

The tautomeric preference of guanylhydrazones towards the azine form induces an unprecedented intramolecular to intermolecular mechanistic switch during the I2-catalyzed oxidative transformation leading to 4,5-disubstituted-3-amino-1,2,4-triazoles in contrast to the reaction of semicarbazones and thiosemicarbazones to form 1,3,4-oxa/thiadiazoles. This intramolecular to intermolecular cyclization shift was established through control experiments and was attributed to the high energy demand (～22 kcal mol-1) for the azine tautomer to adopt the s-cis conformation which is essential for the intramolecular reaction. An I2 induced protocol for an efficient and straightforward synthesis of 4,5-disubstituted-3-amino-1,2,4-triazoles has been developed via tandem oxidative transformation of guanylhydrazones (in its preferentially existing azine tautomeric form) with distinct advantages such as wide substrate scope, use of substoichiometric amounts of iodine, no requirement of external oxidizing agents, base free reaction conditions, short reaction time and moderate to good yields. The role of silver salt in improving the yield and shortening of reaction time was also highlighted.

Rational Design and Synthesis of 1-(Arylideneamino)-4-aryl-1H-imidazole-2-amine Derivatives as Antiplatelet Agents

Based on previous studies indicating the pharmacophoric role of a hydrazone group and azole rings for antiplatelet aggregation activity, a few series of compounds with both hydrazone and an azole (imidazole) ring in their structures were synthesized, and their platelet aggregation inhibitory effects were evaluated. Two of these 1-(arylideneamino)-4-aryl-1H-imidazole-2-amine derivatives, compounds 4 a [(E)-1-(benzylideneamino)-4-phenyl-1H-imidazol-2-amine] and 4 p [(E)-4-phenyl-1-((thiophen-2-ylmethylene)amino)-1H-imidazol-2-amine], exhibited IC50 values similar to that of acetylsalicylic acid against collagen as a platelet aggregation inducer. Structural comparison of the synthesized compounds revealed that those with a para-substituted phenyl ring on the imidazole were among the most active compounds against platelet aggregation induced by arachidonic acid (AA), and the presence of a thiophene ring in these compounds maximized their antiplatelet activity.