3947-97-5

Basic information

• Product Name: 3-phenyl-3-cyclobutene-1,2-dione
• Synonyms: 3-phenyl-3-cyclobutene-1,2-dione;Einecs 223-540-0
• CAS NO: 3947-97-5
• Molecular Formula: C₁₀H₆O₂
• Molecular Weight: 158.15344
• EINECS: 223-540-0
• Mol File: 3947-97-5.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 309.2°Cat760mmHg
• Flash Point: 123.9°C
• Appearance: /
• Density: 1.324g/cm³
• Vapor Pressure: 0.000647mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 3-phenyl-3-cyclobutene-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-3-cyclobutene-1,2-dione(3947-97-5)
• EPA Substance Registry System: 3-phenyl-3-cyclobutene-1,2-dione(3947-97-5)

Safety Data

• Hazardous Substances Data: 3947-97-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthetic Communications, 25, p. 2781, 1995 DOI: 10.1080/00397919508011825

InChI:InChI=1/C10H6O2/c11-9-6-8(10(9)12)7-4-2-1-3-5-7/h1-6H

Upstream product

• 91359-10-3 2-Chloro-3-phenyl-4-phenylsulfanyl-cyclobut-2-enone 
• 3470-35-7 4,4-dichloro-3-phenyl-2-cyclobuten-1-one 
• 109-73-9 N-butylamine 
• 536-74-3 phenylacetylene 
• 15321-51-4 diiron nonacarbonyl 
• 13463-40-6 iron pentacarbonyl 
• 342-60-9 2,4-dichloro-1,1-difluoro-3-phenyl-2-cyclobutene 
• 340-01-2 4,4-dichloro-3,3-difluoro-1-phenyl-cyclobutene 
• 71-43-2 benzene 
• 175225-79-3 3-chloro-2-hydroxy-4-phenyl-2-cyclobuten-1-one 
• 787-18-8 1,1-Difluor-2,4-diethoxy-3-phenyl-cyclobuten 
• 786-02-7 1,1-Difluor-2,2-diethoxy-3-phenyl-cyclobuten 
• 313-28-0 3,3,4,4-Tetrafluor-1-phenyl-cyclobuten-⁽¹⁾ 
• 1495-74-5 1,1-Difluor-2-chlor-4-ethoxy-3-phenyl-cyclobuten-⁽²⁾ 

Downstream Products

• 100518-82-9 2,4-dimethoxy-3-phenyl-cyclobutenone 
• 22315-46-4 bromo-phenyl-cyclobutenedione 
• 22118-93-0 3-chloro-4-(4-phenyl)cyclobut-3-ene-1,2-dione 
• 24804-63-5 3-Hydroxy-2-phenyl-1-<4-methoxy-phenyl>-cyclobuten-(2)-on-(4) 
• 22557-59-1 3-Hydroxy-2-phenyl-1-<4-dimethylamino-phenyl>-cyclobuten-(2)-on-(4) 
• 59735-57-8 2-Methyl-benzoic acid 3-chloro-4-oxo-2-phenyl-cyclobut-1-enyl ester 
• 24804-69-1 1-<2,4-Dimethyl-phenyl>-2-phenyl-cyclobuten-(2)-ol-(3)-on-(4) 
• 24804-64-6 3-Hydroxy-2-phenyl-1-<4-chlorphenyl>-cyclobuten-(2)-on-(4) 
• 34094-57-0 2-Ethyl-2-(3-hydroxy-4-oxo-2-phenyl-cyclobut-2-enyl)-malonic acid diethyl ester 
• 23094-27-1 2-(2.4-Dichlor-benzoyloxy)-3-phenyl-4-chlor-cyclobuten-⁽²⁾-on 
• 24804-70-4 3-phenyl-4-p-tolyl-cyclobutane-1,2-dione 
• 24804-62-4 3-Hydroxy-2-phenyl-1-<4-aethoxy-phenyl>-cyclobuten-(2)-on-(4) 
• 59735-54-5 3-Fluoro-benzoic acid 3-chloro-4-oxo-2-phenyl-cyclobut-1-enyl ester 
• 33900-68-4 4-Bromo-benzoic acid 3-chloro-4-oxo-2-phenyl-cyclobut-1-enyl ester 

Relevant articles and documents

Novel reaction of the [HFe3(CO)11]- reagent with alkynes: A new synthesis of cyclobutenediones

Reaction of the [HFe3(CO)11]- species generated in situ using Fe(CO)5 and NaBH4/CH3COOH in THF with alkynes, followed by CuCl2.2H2O oxidation leads to the corresponding cyclobutenediones in 60-73% yields.

Reactive iron carbonyl reagents via reaction of metal alkoxides with Fe(CO)5 or Fe2(CO)9: Synthesis of cyclobutenediones via double carbonylation of alkynes

Alkoxy bases such as t-BuOK react with Fe(CO)5 to give reactive iron carbonyl intermediates that in turn react with alkynes at 70 °C in THF to give 1,2-cyclobutenediones in 70-93% yields after CuCl2· 2H2O oxidation. A novel 1,2-diacyloxyferrole derivative was isolated in the reaction of diphenylacetylene with Fe(CO)5/t-BuOK in the presence of acetyl chloride in contrast to the formation of a 1,4-diacyloxyferrole complex formed in the reaction using Fe(CO) 5/Me3NO. The Fe2(CO)9/t-BuOK reagent system also converts the alkynes to corresponding cyclobutenediones in 63-90% yields under similar reaction conditions.

Amine induced carbonylation of alkynes to cyclobutenediones using Fe3(CO)12

Iron carbonyl species, prepared in situ in THF using Fe3(CO)12, react with alkynes at 25°C, in the presence of certain amines, to give the corresponding cyclobutenediones in moderate to good yields (25-61%) after CuCl2·2H

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.