3859-41-4

Basic information

• Product Name: 1,3-Cyclopentanedione
• Synonyms: 1,3-Cyclopentadione;1,3-CYCLOPENTANEDIONE;CYCLOPENTANE-1,3-DIONE;Cyclopentanedione;1,3-CYCLOPENTANEDIONE 98+%;Pentan-1,3-dione;1,3-Cyclopentanedione,99%;1,3-Cyclopentandion
• CAS NO: 3859-41-4
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.1
• EINECS: 223-372-8
• Product Categories: Carbonyl Compounds;pharmacetical;ketone;Ring Systems;C3 to C6;Carbonyl Compounds;Ketones
• Mol File: 3859-41-4.mol
• Article Data: 22

Chemical Properties

• Melting Point: 149-151 °C(lit.)
• Boiling Point: 143.59°C (rough estimate)
• Flash Point: 80.1 °C
• Appearance: white to brown/Crystalline Powder
• Density: 1.1008 (rough estimate)
• Vapor Pressure: 0.0374mmHg at 25°C
• Refractive Index: 1.4400 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO, Ethyl Acetate
• PKA: 8.94±0.20(Predicted)
• Water Solubility: Very soluble in water.
• BRN: 1362728
• CAS DataBase Reference: 1,3-Cyclopentanedione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclopentanedione(3859-41-4)
• EPA Substance Registry System: 1,3-Cyclopentanedione(3859-41-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• Hazardous Substances Data: 3859-41-4(Hazardous Substances Data)

Usage

Chemical Properties

white to cream crystalline powder

Uses

Different sources of media describe the Uses of 3859-41-4 differently. You can refer to the following data:
1. 1,3-Cyclopentanedione was used in the synthesis of chemical probes for selective labeling of sulfenic acid proteins. It was also used to synthesize enaminones with possible anticonvulsant activity.
2. 1,3-Cyclopentanedione was used in the synthesis of chemical probes for selective labeling of sulfenic acid proteins.

Synthesis Reference(s)

Journal of the American Chemical Society, 102, p. 2095, 1980 DOI: 10.1021/ja00526a059

Purification Methods

Purify the dione by Soxhlet extraction with CHCl3. The CHCl3 is evaporated and the residue is recrystallised from EtOAc and/or sublimed at 120o/4mm. [IR: Boothe et al. J Am Chem Soc 75 1732 1953, DePuy & Zaweski J Am Chem Soc 81 4920 1959, Beilstein 7 IV 1981.]

InChI:InChI=1/C5H6O2/c6-4-1-2-5(7)3-4/h3,6H,1-2H2

Upstream product

• 14000-78-3 6-Ethyl 1-methyl 3-oxohexane-1,6-dioate 
• 930-60-9 maleic anhydride 
• 3859-39-0 2-acetylcyclopentane-1,3-dione 
• 14734-21-5 2,5-dioxo-cyclopentanecarboxylic acid ethyl ester 
• 14734-23-7 2-Carbaethoxy-4-carbo-tert.-butoxy-cyclopentan-1.3-dion 
• 130249-17-1 2,3-epoxycyclopentanone 
• 279-35-6 1,3-epiperoxycyclopentane 
• 59995-47-0 4-Hydroxycyclopent-2-enone 
• 73825-35-1 3-(N-phenylamino)-2-cyclopentene-1-one 
• 78743-55-2 2-Hydroxy-2-methoxymethyl-cyclobutanone 
• 109459-59-8 1,4-dioxaspiro[4.4]nonan-7-one 
• 91920-55-7 methyl 1-hydroxy-4-oxocyclopent-2-enecarboxylate 
• 120-92-3 cyclopentanone 
• 41498-13-9 4,5-diiodo-4-cyclopentene-1,3-dione 

Downstream Products

• 4683-50-5 3-methoxycyclopent-2-enone 
• 22627-70-9 3-ethoxycyclopent-2-en-1-one 
• 53102-14-0 3-chlorocyclopent-2-en-1-one 
• 150111-61-8 3-Hydroxy-2-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one 
• 504-02-9 1,3-cylohexanedione 
• 102306-78-5 6,7-dihydrocyclopenta[d][1,3]dioxin-5(4H)-one 
• 114908-47-3 C₁₃H₁₄O₅ 
• 77902-69-3 C₁₁H₈N₃O₈^(1-) 
• 142605-82-1 2,2,9,9-tetrakis(4-methoxyphenyl)octahydro-3,4,7,8-tetraoxabenzindene-4a,6a-diol 
• 112621-25-7 2-(4-hydroxybenzyl)cyclopentane-1,3-dione 
• 92774-85-1 3-Hydroxy-2-(2-nitro-1-p-tolyl-ethyl)-cyclopent-2-enone 
• 129836-54-0 C₁₈H₁₈O₄ 
• 70359-69-2 2-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenylidene]-cyclopentane-1,3-dione 
• 142605-83-2 2,2,9,9-tetrakis(4-fluorophenyl)octahydro-3,4,7,8-tetraoxabenzindene-4a,6a-diol 

Relevant articles and documents

KINETIC RESOLUTION OF 4-HYDROXY-2-CYCLOPENTENONE BY RHODIUM-CATALYZED ASYMMETRIC ISOMERIZATION

Cationic Rh-BINAP complexes catalyze isomerization of racemic 4-hydroxy-2-cyclopentenone to 1,3-cyclopentadione with 5:1 enantiomeric discrimination.

Rapid and Multigram Synthesis of Vinylogous Esters under Continuous Flow: An Access to Transetherification and Reverse Reaction of Vinylogous Esters

An environmentally benign approach for the synthesis of vinylogous esters from 1,3-diketone and its reverse reaction under continuous-flow has been developed with alcohols in the presence of inexpensive Amberlyst-15 as a catalyst. This methodology is highly selective and general for a range of cyclic 1,3-dicarbonyl compounds which gives a library of linear alkylated and arylated vinylogous esters in good to excellent yield under solvent and metal free condition. Furthermore, the long-time experiment in a continuous-flow up to 40 h afforded 8.0 g of the vinylogous ester with turnover number (TON) = 28.6 and turnover frequency (TOF) = 0.715 h-1 using Amberlyst-15 as a catalyst. Furthermore, a continuous-flow sequential transetherification of vinylogous esters with various alcohols has been achieved in high yield. Reversibly, this vinylogous ester was deprotected or hydrolyzed into ketone using environmentally benign water as a solvent and Amberlyst-15 as a catalyst under continuous-flow process.

PROCESS FOR PRODUCTION OF SUBSTITUTED CYCLOPENTANONE

A substituted cyclopentanone represented by the formula (2) can be produced by hydrogenating the double bond in a compound represented by the formula (1) in the presence of a transition metal catalyst by using a carboxylic acid or a specific concentration of a carboxylic acid ester as a solvent. This process can produce a substituted cyclopentanone which is useful as an jasmine-flavored fragrance, an intermediate in the production of the fragrance or the like, in a simple and inexpensive manner at a high cis-form ratio; (1) wherein R1 and R2 represent a substituent having 1 to 8 carbon atoms; and (2) wherein R3 and R4 represent a substituent having 1 to 8 carbon atoms, may be the same as R1 and R2, and may be the same as each other.