22315-46-4

Basic information

• Product Name: 3-Cyclobutene-1,2-dione, 3-bromo-4-phenyl-
• CAS NO: 22315-46-4
• Molecular Formula: C10H5BrO2
• Molecular Weight: 237.052
• Mol File: 22315-46-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-Cyclobutene-1,2-dione, 3-bromo-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclobutene-1,2-dione, 3-bromo-4-phenyl-(22315-46-4)
• EPA Substance Registry System: 3-Cyclobutene-1,2-dione, 3-bromo-4-phenyl-(22315-46-4)

Safety Data

• Hazardous Substances Data: 22315-46-4(Hazardous Substances Data)

Upstream product

• 313-28-0 3,3,4,4-Tetrafluor-1-phenyl-cyclobuten-⁽¹⁾ 
• 313-29-1 4-Fluor-4-chlor-1-phenyl-cyclobuten-⁽¹⁾-on-⁽³⁾ 
• 313-30-4 4,4-Difluoro-3-phenyl-cyclobuten-⁽²⁾-on-⁽¹⁾ 
• 313-27-9 1-phenyl-3,3,4-trifluoro-4-chloro-1-cyclobutene 
• 128242-44-4 3-(1-methylethoxy)-4-phenyl-3-cyclobutene-1,2-dione 2-ethylene acetal 
• 3947-97-5 3-phenyl-3-cyclobutene-1,2-dione 

Downstream Products

• 36048-56-3 (2-morpholin-4-yl-cyclopent-1-enyl)-phenyl-cyclobutenedione 
• 36048-57-4 (2-morpholin-4-yl-cyclohex-1-enyl)-phenyl-cyclobutenedione 
• 76098-50-5 N-(3,4-Dioxo-2-phenyl-cyclobut-1-enyl)-pyrrolidine-1-carboximidoyl bromide 
• 22557-32-0 1-Phenyl-2-(2-methoxy-anilino)-cyclobuten-⁽¹⁾-dion-(3,4) 
• 22557-38-6 1-Phenyl-2-(2-carboxyanilino)-cyclobuten-⁽¹⁾-dion-(3,4) 
• 24804-50-0 1-(4-Methoxy-phenyl)-2-phenyl-cyclobuten-⁽¹⁾-dion-(3,4) 
• 22557-56-8 1-Phenyl-2--cyclobuten-(1)-dion-(3.4) 
• 22557-36-4 1-Phenyl-2-(2-nitro-p-toluidino)-cyclobuten-⁽¹⁾-dion-(3,4) 
• 72807-81-9 2-(3,4-Dioxo-2-phenyl-cyclobut-1-enyl)-1,3-di-p-tolyl-isothiourea 
• 711-78-4 3-methoxy-4-phenylcyclobutenedione 
• 61509-83-9 2-(3,4-Dioxo-2-phenyl-1-cyclobuten-1-yl)-2-(triphenylphosphoranyliden)essigsaeureethylester 
• 63676-78-8 (2Z)-2-(4-Oxo-3-phenoxy-2-phenyl-2-cyclobuten-1-yliden)essigsaeure-ethylester 
• 36048-47-2 1-(Ethoxycarbonyl-methyl)-2-phenyl-cyclobutendion-(3,4) 
• 36048-53-0 3-(2-Oxo-cyclooctyl)-4-phenyl-cyclobut-3-ene-1,2-dione 

Relevant articles and documents

Generation of 1,2-bisketenes from cyclobutene-1,2-diones by flash photolysis and ring closure kinetics

The interconversion of cyclobutene-1,2-diones (1) and 1,2-bisketenes (RC-C-O)2 has been surveyed for different combinations of substituents R = H, Me, t-Bu, Ph, Me3Si, CN, Cl, Br, R1O, alkynyl, and PhS. The bisketenes 2 have been generated by flash photolysis, and the kinetics of their conversion to 1 have been studied by time-resolved infrared and ultraviolet spectroscopy. The rate constants of the ring closure of 2 are correlated by the ketene stabilization parameters (SE) and with calculated barriers. The rate constant of ring closure of the di-tert-butyl bisketene 2g to cyclobutenedione 1g is only 40 times smaller than for the dimethyl analogue, showing a rather modest steric barrier. The quinoketene 2s has a fast rate of ring closure, but not as fast as anticipated on the basis of calculated geometric and thermodynamic factors. A lag in the attainment of aromatic stabilization in the transition structure for ring closure is a possible cause of this diminished reactivity.