145693-89-6

Basic information

• Product Name: 4-Imidazolidinone, 3-phenyl-5-(2-pyridinylmethylene)-2-thioxo-, (Z)-
• CAS NO: 145693-89-6
• Molecular Formula: C15H11N3OS
• Molecular Weight: 281.338
• Mol File: 145693-89-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4-Imidazolidinone, 3-phenyl-5-(2-pyridinylmethylene)-2-thioxo-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Imidazolidinone, 3-phenyl-5-(2-pyridinylmethylene)-2-thioxo-, (Z)-(145693-89-6)
• EPA Substance Registry System: 4-Imidazolidinone, 3-phenyl-5-(2-pyridinylmethylene)-2-thioxo-, (Z)-(145693-89-6)

Safety Data

• Hazardous Substances Data: 145693-89-6(Hazardous Substances Data)

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 2010-15-3 3-phenyl-2-thioxoimidazolidin-4-one 
• 62-53-3 aniline 
• 104892-41-3 ethyl N-(phenylaminothiocarbonyl)glycinate 
• 103-72-0 phenyl isothiocyanate 
• 2215-20-5 2-[(phenylcarbamothioyl)amino]acetic acid 

Downstream Products

• 916747-72-3 (5Z,5'Z)-2,2'-(ethane-1,2-diyldisulfanyldiyl)bis(5-(pyridine-2-ylmethylene)-3-phenyl-3,5-dihydro-4H-imidazole-4-one) 
• 916747-75-6 (5Z,5'Z)-2.2'-(decane-1,10-diyldisulfanyldiyl)bis(3-phenyl-5-(2-pyridylmethylene)-3,5-dihydro-4H-imidazol-4-one) 
• 916747-74-5 (5Z,5'Z)-2.2'-(octane-1,8-diyldisulfanyldiyl)bis(3-phenyl-5-(2-pyridylmethylene)-3,5-dihydro-4H-imidazol-4-one) 
• 874755-87-0 (5Z)-3-methyl-2-methylthio-5-(α-pyridylmethylidene)-3,5-dihydro-4H-imidazol-4-one 

Relevant articles and documents

Polymorphism of 5-(pyridin-2-ylmethylene)-3-phenyl-2-methylthio-3,5- dihydro-4H-imidazole-4-one

The title compound, C16H13N3OS (1), exists in three polymorphic forms. Crystalline 1 undergoes an enantiotropic, first-order, k2 phase transition at 262.9(5) K with ΔH = 0.3(1) kJ mol-1. Upon cooling below the transition temperature, the high temperature orthorhombic polymorph (Form I, space group Pbcm) transforms into a low temperature orthorhombic polymorph (Form II, space group Pbca) with a unit cell twice the size of that of the Form I. A molten 1 can be cooled in a controlled fashion to generate a monoclinic Form III of 1 with the unit cell size similar to that of Form I. Metastable Form III, once isolated, is indefinitely stable between 100 K and its melting point of 466 K. If crystals of Form III are in contact with seed crystals of Form I, a monotropic t2 first-order Form III → Form I phase transition occurs upon heating with the onset between 420 and 448 K and ΔH = -1.7(4) kJ mol-1. The most substantial differences among the molecular geometries of 1 in Forms I-III are observed in the position and tilt of the phenyl ring relative to the rest of the molecule. The packing in Form III is very different from those in the other polymorphs. DFT molecular geometry optimizations produce the following order of stable molecule configurations: Form II (most stable), Form I (0.50 kJ mol -1), Form III (2.81 kJ mol-1).

Synthesis of isomeric 3-phenyl-5-(pyridylmethylene)-2-thiohydantoins and their S-methylated derivatives. Molecular and crystal structures of (5Z)-3-phenyl-5-(pyridin-2-ylmethylene)-2-thiohydantoin and (5Z)-2-methylthio-3- phenyl-5-(pyridin-2-ylmethylene)-

Three procedures were used for the synthesis of α-, β, and γ-pyridyl-substituted (5Z)-3-phenyl-5-(pyridylmethylene)-2-thiohydantoins: the reaction of 2-thiohydantoin with the corresponding aldehyde in AcOH in the presence of AcONa, the two-step one-pot sy