26831-63-0

Basic information

• Product Name: 3-Hydroxycyclopentanone
• Synonyms: 3-Hydroxycyclopentanone;3-hydroxycyclopentan-1-one
• CAS NO: 26831-63-0
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.11582
• Mol File: 26831-63-0.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 210.0±33.0 °C(Predicted)
• Appearance: /
• Density: 1.217±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 14.15±0.20(Predicted)
• CAS DataBase Reference: 3-Hydroxycyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxycyclopentanone(26831-63-0)
• EPA Substance Registry System: 3-Hydroxycyclopentanone(26831-63-0)

Safety Data

• Hazardous Substances Data: 26831-63-0(Hazardous Substances Data)

Usage

General Description

3-Hydroxycyclopentanone is a chemical compound with the molecular formula C5H8O2. It is a cyclic ketone with a hydroxyl group attached to a five-membered ring. 3-Hydroxycyclopentanone is a colorless liquid that is soluble in water and is commonly used as a building block in organic synthesis. It is often used as a reagent in the production of various pharmaceuticals and fine chemicals due to its ability to undergo various chemical reactions, such as oxidation and reduction, to yield different derivatives. Additionally, 3-Hydroxycyclopentanone has potential applications in the fragrance and flavor industry due to its unique structure and reactivity. Overall, this compound has important industrial and synthetic applications due to its versatile chemical properties.

Upstream product

• 279-35-6 1,3-epiperoxycyclopentane 
• 98-00-0 (2-furyl)methyl alcohol 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 88867-81-6 2,3-dioxabicyclo<2.2.1>heptane-1-d 

Downstream Products

• 16326-97-9 cis-cyclopentane-1,3-diol 

Relevant articles and documents

Prostaglandin Endoperoxides. 11. Mechanism of Amine-Catalyzed Fragmentation of 2,3-Dioxabicycloheptane

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Industrially scalable and cost-effective synthesis of 1,3-cyclopentanediol with furfuryl alcohol from lignocellulose

A new route for the selective synthesis of renewable 1,3-cyclopentanediol was developed by the aqueous phase rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone followed by hydrogenation. The presence of a small amount of base catalysts is beneficial for the aqueous phase rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone. Such a promotion effect of base catalysts can be rationalized by restraining the generation of levulinic acid which may catalyze the polymerization of furfuryl alcohol. In the hydrogenation of 4-hydroxycyclopent-2-enone to 1,3-cyclopentanediol, an evident solvent effect was noticed. Higher carbon yields of 1,3-cyclopentanediol were obtained when tetrahydrofuran was used as the solvent. In the large scale tests with high initial concentrations of feedstocks, a high overall carbon yield (72.0%) of 1,3-cyclopentanediol was achieved over cheap catalysts (MgAl-HT and RANEY Ni). As a potential application, 1,3-cyclopentanediol as obtained was successfully used as a monomer in the synthesis of polyurethane.

Ruthenium(II)-Catalyzed Reactions of 1,4-Epiperoxides

The behavior of 1,4-epiperoxides in the presence of transition-metal complexes is highly dependent on the structures of the substrates and the nature of the metal catalysts.Reaction of saturated epiperoxides such as 1,3-epiperoxycyclopentane, 1,4-epiperoxycyclohexane, or dihydroascaridole catalyzed by RuCl2(PPh3)3 in dichloromethane gives a mixture of products arising from fragmentation, rearrangement, reduction, disproportionation, etc.Prostaglandin H2 methyl ester undergoes clean and stereospecific fragmentation to afford methyl(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoate and malonaldehyde.Bicyclic 2,3-didehydro 1,4-epiperoxides give the syn-1,2:3,4-diepoxides by the same catalyst.The monocyclic analogues are transformed to a mixture of diepoxides and furan products.The stereochemical outcome of the epoxide formation reflects unique differences in the ground-state geometry of the starting epiperoxide substrates.FeCl2(PPh3)2 serves as a useful catalyst for the skeletal change of sterically hindered bicyclic 2,3-didehydro 1,4-epiperoxides to the syn-diepoxides.In addition, the Fe complex best effects the conversion of 1,4-unsubstituted 2,3-didehydro epiperoxides to furans.The Ru-catalyzed reactions are interpreted in terms of the intermediacy of inner-sphere radicals formed by atom transfer of the Ru(II) species to peroxy substrates, in contrast to the Fe-catalyzed reactions proceeding via free, outer-sphere radicals generated by an electron-transfer mechanism.