13177-38-3

Basic information

• Product Name: cyclopenta-2,4-dien-1-one
• Synonyms: 2,4-cyclopentadien-1-one; 2,4-Cyclopentadiene-1-one; Cyclopenta-2,4-dien-1-one
• CAS NO: 13177-38-3
• Molecular Formula: C₅H₄O
• Molecular Weight: 80.0847
• Mol File: 13177-38-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 164.7°C at 760 mmHg
• Flash Point: 54.5°C
• Density: 1.115g/cm³
• Vapor Pressure: 1.94mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: cyclopenta-2,4-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: cyclopenta-2,4-dien-1-one(13177-38-3)
• EPA Substance Registry System: cyclopenta-2,4-dien-1-one(13177-38-3)

Safety Data

• Hazardous Substances Data: 13177-38-3(Hazardous Substances Data)

Usage

General Description

Cyclopenta-2,4-dien-1-one is an organic compound that falls under the category of cyclic enones, specifically a conjugated cyclodienone. It has a molecular formula of C5H4O and a molecular weight of 80.09 g/mol. The structure is so named for its pentagonal ring structure (cyclopentane) with two double bonds (diene) and a ketone group (one). It exhibits desirable properties such as excellent chemical stability and heat resistance, making it a useful chemical in the fields of organic synthesis, polymer chemistry, and material science. In addition to its aromatic nature, cyclopenta-2,4-dien-1-one also shows potential bioactivity, although its direct applications in the field of medicine are still under investigation.

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Relevant articles and documents

The Photo-isomerization of Cyclopentadienone O-Oxide Isolated in Low Temperature Matrices

Discrepancies in recent reports from different laboratories on the i.r. spectrum of matrix-isolated cyclopentadienone O-oxide have now been reconciled by showing that two distinct isomers may be formed from cyclopentadienylidene and O2, and that one, a carbonyl oxide, may be converted photolytically into the other, a dioxirane.

Binuclear ruthenium(III) bis(thiosemicarbazone) complexes: Synthesis, spectral, electrochemical studies and catalytic oxidation of alcohol

(Chemical Equation Presented).A new series of binuclear ruthenium(III) thiosemicarbazone complexes of general formula [(EPh3)2 (X)2Ru-L-Ru(X)2(EPh3)2] (where E = P or As; X = Cl or Br; L = NS chelating bis(thiosemicarbazone ligands) has been synthesized and characterized by analytical and spectral (FT-IR, UV-Vis and EPR). IR spectra show that the thiosemicarbazones behave as monoanionic bidentate ligands coordinating through the azomethine nitrogen and thiolate sulphur. The electronic spectra of the complexes indicate that the presence of d-d and intense LMCT transitions in the visible region. The complexes are paramagnetic (low spin d5) in nature and all the complexes show rhombic distortion around the ruthenium ion with three different 'g' values (gx ≠ gy ≠ gz) at 77 K. All the complexes are redox active and exhibit an irreversible metal centered redox processes (RuIII-RuIII/RuIV-RuIV; RuIII-RuIII/RuII-RuII) within the potential range of 0.38- 0.86 V and -0.39 to -0.66 V respectively, versus Ag/AgCl. Further, the catalytic efficiency of one of the complexes [Ru2Cl2(AsPh3)4(L1)] (4) has been investigated in the case of oxidation of primary and secondary alcohols into their corresponding aldehydes and ketones in the presence of N-methylmorpholine- N-oxide(NMO) as co-oxidant. The formation of high valent RuV@O species is proposed as catalytic intermediate for the catalytic cycle.

Cyclopentadienone O-Oxide: A Highly Labile Intermediate in the Matrix Reaction between Cyclopentadienylidene and Oxygen

Cyclopentadienylidene reacts with oxygen in low-temperature matrices, giving a photolabile intermediate, the i.r. spectrum of which suggests that it is the carbonyl oxide, cyclopentadienone O-oxide.

Parabenzoquinone pyrolysis and oxidation in a flow reactor

An experimental and theoretical study of the pyrolysis and oxidation of parabenzoquinone has been performed. The experiments were conducted in an isothermal quartz flow reactor at atmospheric pressure in the temperature range 600-1500 K. The main variables considered are temperature, oxygen concentration, and presence of CO. A detailed reaction mechanism for the pyrolysis and oxidation chemistry of parabenzoquinone is proposed, which provides a good description of the experimental results. Both the experimental work and the kinetic mechanism proposed for the pyrolysis and oxidation of parabenzoquinone represent the first systematic study carried out for this important aromatic compound. Our pyrolysis results confirm that the primary dissociation channel for p-benzoquinone leads to CO and a C5H4O isomer, presumably cyclopentadienone. However, significant formation of CO2 during the pyrolysis may indicate the existence of a secondary dissociation channel leading to CO2 and a C5H4 isomer. Under oxidizing conditions, consumption of p-benzoquinone occurs mainly by dissociation at lower temperatures. As the temperature increases interaction of OC6H4O with the radical pool becomes more significant, occurring primarily through hydrogen abstraction reactions followed by ring opening reactions of the OC6H3O radical.