2-Methyl-1,3-cyclopentanedione

Base Information

• Chemical Name: 2-Methyl-1,3-cyclopentanedione
• CAS No.: 765-69-5
• Molecular Formula: C6H8O2
• Molecular Weight: 112.128
• Hs Code.: 29142900
• European Community (EC) Number: 212-153-2
• NSC Number: 54458
• UNII: C9LG5VP01C
• DSSTox Substance ID: DTXSID30227309
• Nikkaji Number: J110.437C
• Wikidata: Q27896539
• Metabolomics Workbench ID: 132885
• ChEMBL ID: CHEMBL363186
• Mol file: 765-69-5.mol

Synonyms:2-Methyl-1,3-cyclopentadione;NSC 54458;

Chemical Property of 2-Methyl-1,3-cyclopentanedione

Chemical Property:

• Appearance/Colour: light beige to tan crystalline powder
• Vapor Pressure: 0.0392mmHg at 25°C
• Melting Point: 212-215 °C(lit.)
• Refractive Index: 1.548
• Boiling Point: 218 °C at 760 mmHg
• PKA: 10.83±0.20(Predicted)
• Flash Point: 78.5 °C
• PSA: 34.14000
• Density: 1.102 g/cm³
• LogP: 0.55450
• Storage Temp.: Store below +30°C.
• Solubility.: Solubility in hot Methanol (almost transparency).
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

2-[Methyl-1- ^*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:

• Canonical SMILES: CC1C(=O)CCC1=O
• Uses: 2-Methyl-1,3-cyclopentanedione was used as a reactant in the identification and characterization of benzil (diphenylethane-1,2-dione) analogues as inhibitors of mammalian carboxylesterases. 2-Methyl-1,3-cyclopentanedione hs been used to explore deoxycholic acid (DCA) induced changes in cell signaling. DCA is a secondary bile acid implicated in numerous pathological conditions. It has also been used in the synthesis of (-)-curcumanolide A and (-)-curcumalactone by aldol-lactonization.

Technology Process of 2-Methyl-1,3-cyclopentanedione

There total 15 articles about 2-Methyl-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: 69.0%

Co{(N4C19H6(CH3)8)(CH2CH2COOC3H7)4(CH2COOC3H7)3}(CH2CHC(O)CH2CH2C(O))(1+) → 2-Methylcyclopentane-1,3-dione (765-69-5) + 1,4-Cyclohexanedione (637-88-7)

Guidance literature:

In methanol; Irradiation (UV/VIS); anaerobic irradiation 1h with visible light at 20°C; analyzing products by GLC;

DOI:10.1246/cl.1988.621

Reference yield: 68.0%

tert-Butyl peroxybenzoate (614-45-9) + 1,3-cyclopentadione (3859-41-4) → 2-Methylcyclopentane-1,3-dione (765-69-5)

Guidance literature:

With acetic acid; copper(l) chloride; at 120 ℃;

Reference yield: 63.0%

succinic acid (110-15-6) + propionyl chloride (79-03-8) → 2-Methylcyclopentane-1,3-dione (765-69-5)

Guidance literature:

succinic acid; With aluminum (III) chloride; nitromethane; at 20 ℃; for 1h; Inert atmosphere;

propionyl chloride; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01622

upstream raw materials:

3-methylcyclopentane-1,2,4-trione

succinic acid anhydride

propionyl chloride

succinic acid

Downstream raw materials:

(+/-)-7a-methyl-2,3,7,7a,tetrahydro-1H-indene-1,5(6H)-dione

2-methyl-2-(3-oxobutyl)-1,3-cyclopentanedione

2-allyl-2-methyl-1,3-cyclopentanedione

2-methyl-2-(2-phenyl-2-oxoethyl)-1,3-cyclopentanedione

Refernces

• 1、 Armaly, Ahlam M.,Bar, Sukanta,Schindler, Corinna S.. "Aluminum Chloride-Mediated Dieckmann Cyclization for the Synthesis of Cyclic 2-Alkyl-1,3-alkanediones: One-Step Synthesis of the Chiloglottones". supporting information. p. 3958 - 3961. Retrieved 2017/08/15.
• 2、 Isart, Carles,Bastida, David,Bures, Jordi,Vilarrasa, Jaume. "Gold(III) complexes catalyze deoximations/transoximations at neutral pH". experimental part. p. 3275 - 3279. Retrieved 2011/05/12.