1,3-Cyclopentanedione

Base Information

• Chemical Name: 1,3-Cyclopentanedione
• CAS No.: 3859-41-4
• Molecular Formula: C5H6O2
• Molecular Weight: 98.1014
• Hs Code.: 29142900
• European Community (EC) Number: 223-372-8
• NSC Number: 364015
• UNII: 98107S5K06
• DSSTox Substance ID: DTXSID90191911
• Nikkaji Number: J1.826K
• Wikipedia: 1,3-Cyclopentanedione
• Wikidata: Q27104474
• Metabolomics Workbench ID: 52284
• ChEMBL ID: CHEMBL224233
• Mol file: 3859-41-4.mol

Synonyms:1,3-Cyclopentanedione;Cyclopentane-1,3-dione;3859-41-4;1,3-Cyclopentadione;MFCD00001405;CHEBI:41456;UNII-98107S5K06;EINECS 223-372-8;NSC-364015;98107S5K06;1.3-CYCLOPENTANEDIONE;1,3cyclopentadione;1,3 cyclopentadione;1,3-cyclopentandione;cyclopentan-1,3-dione;1,3-cyclopentane dione;cyclopentane-1,3-quinone;CEJ;1,3-Cyclopentanedione, 97%;BDBM7813;CHEMBL224233;LOGSONSNCYTHPS-UHFFFAOYSA-;DTXSID90191911;CS-D0815;STR07692;BBL011146;NSC364015;STK802459;AKOS000278923;AC-1796;NSC 364015;PB47422;NCGC00336891-01;SY003377;A6527;AM20100026;FT-0606601;EN300-35672;AB01329887-02;W-111717;Q27104474;F0001-1098

Chemical Property of 1,3-Cyclopentanedione

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0.0374mmHg at 25°C
• Melting Point: 149-151 °C(lit.)
• Refractive Index: 1.577
• Boiling Point: 221.8 °C at 760 mmHg
• PKA: 8.94±0.20(Predicted)
• Flash Point: 80.1 °C
• PSA: 34.14000
• Density: 1.2 g/cm³
• LogP: 0.30850
• Storage Temp.: 0-6°C
• Solubility.: DMSO, Ethyl Acetate
• Water Solubility.: Very soluble in water.
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 98.036779430
• Heavy Atom Count: 7
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

1,3-Cyclopentanedione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: C1CC(=O)CC1=O
• Uses: 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. 1,3-Cyclopentanedione was used in the synthesis of chemical probes for selective labeling of sulfenic acid proteins.

Technology Process of 1,3-Cyclopentanedione

There total 32 articles about 1,3-Cyclopentanedione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

4-Hydroxycyclopent-2-enone (59995-47-0,59995-49-2,61305-27-9,61740-29-2) → 1,3-cyclopentadione (3859-41-4)

Guidance literature:

With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); In 2-methyltetrahydrofuran; at 80 ℃; for 4h; Solvent; Temperature; Schlenk technique; Inert atmosphere; Sealed tube; Green chemistry;

DOI:10.1039/d1gc02372a

Reference yield: 99.0%

3-(propoxy)cyclopent-2-en-1-one → 1,3-cyclopentadione (3859-41-4)

Guidance literature:

With water; In acetonitrile; at 20 ℃; for 0.226667h; under 900.09 Torr; Flow reactor;

DOI:10.1021/acs.oprd.9b00067

Reference yield: 94.0%

2,3-epoxycyclopentanone (130249-17-1,6705-52-8) → 1,3-cyclopentadione (3859-41-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,2-bis-(diphenylphosphino)ethane; In toluene; at 80 ℃; for 25h;

DOI:10.1021/ja00526a059

upstream raw materials:

6-Ethyl 1-methyl 3-oxohexane-1,6-dioate

maleic anhydride

2-acetylcyclopentane-1,3-dione

2,5-dioxo-cyclopentanecarboxylic acid ethyl ester

Downstream raw materials:

3-methoxycyclopent-2-enone

3-ethoxycyclopent-2-en-1-one

3-chlorocyclopent-2-en-1-one

4-oxo-2-phenyl-1,2,3,4,5,6-hexahydro-1-oxapentalene

Refernces

• 1、 Alsters, Paul L.,De Wildeman, Stefaan M. A.,Hadavi, Darya,Han, Peiliang,Mogensen, Siri,Monsegue, Luciano G.,Noordijk, Jurrie,Quaedflieg, Peter J. L. M.,Verzijl, Gerard K. M.,van Slagmaat, Christian A. M. R.. "Bio-based synthesis of cyclopentane-1,3-diamine and its application in bifunctional monomers for poly-condensation". . p. 7100 - 7114. Retrieved 2021/09/28.
• 2、 Pingen, Dennis,Diebolt, Olivier,Vogt, Dieter. "Direct amination of bio-alcohols using ammonia". . p. 2905 - 2912. Retrieved 2013/10/21.