2,2-Dimethyl-1,3-cyclopentanedione

Base Information

• Chemical Name: 2,2-Dimethyl-1,3-cyclopentanedione
• CAS No.: 3883-58-7
• Molecular Formula: C7H10O2
• Molecular Weight: 126.155
• Hs Code.: 2914299000
• DSSTox Substance ID: DTXSID90192100
• Nikkaji Number: J145.024G
• Wikidata: Q83064721
• Mol file: 3883-58-7.mol

Synonyms:2,2-Dimethyl-1,3-cyclopentanedione;3883-58-7;2,2-dimethylcyclopentane-1,3-dione;1,3-Cyclopentanedione, 2,2-dimethyl-;2,2-dimethyl-cyclopentane-1,3-dione;ghl.PD_Mitscher_leg0.127;SCHEMBL660844;DTXSID90192100;MFCD00074900;STL227693;AKOS004120700;DS-16688;CS-0153883;C74976;A849789

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

Chemical Property:

• Vapor Pressure: 0.164mmHg at 25°C
• Melting Point: 46-47 °C
• Boiling Point: 213.4°C at 760 mmHg
• Flash Point: 76.5°C
• PSA: 34.14000
• Density: 1.05g/cm³
• LogP: 0.94460
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

2,2-DIMETHYL-1,3-CYCLOPENTANEDIONE AldrichCPR ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)CCC1=O)C

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

There total 15 articles about 2,2-Dimethyl-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: 93.0%

2-Methylcyclopentane-1,3-dione (765-69-5) + methyl iodide (74-88-4) → 2,2-dimethylcyclopentane-1,3-dione (3883-58-7)

Guidance literature:

2-Methylcyclopentane-1,3-dione; methyl iodide; With potassium hydroxide; In 1,4-dioxane; water; Heating / reflux;

With hydrogenchloride; In water; at 120 ℃; for 0.25h;

Reference yield: 82.0%

3,3-Dimethyl-2,4-dioxo-cyclopentanecarboxylic acid ethyl ester (57613-21-5) → 2,2-dimethylcyclopentane-1,3-dione (3883-58-7)

Guidance literature:

With hydrogenchloride; at 70 ℃; for 3h;

DOI:10.1055/s-1986-31800

Reference yield: 74.0%

2,2-dimethyl-1,3-dioxane (695-30-7) + 1,2-bis(trimethylsiloxy)cyclobutene (17082-61-0) → 2,2-dimethylcyclopentane-1,3-dione (3883-58-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/0040-4039(96)01409-8

upstream raw materials:

2-Methylcyclopentane-1,3-dione

dimethyl sulfate

methyl iodide

dimethyl(methylthio)sulfonium tetrafluoroborate

Refernces

• 1、 Parker, Kathlyn A.,Koziski, Kathleen A.,Breault, Gloria. "SYNTHESIS OF 2,2-DISUBSTITUTED 4,9-DIHYDROXY-1H-BENZ(f)INDENE-1,3(2H)DIONES. A MODEL SEQUENCE FOR THE SYNTHESIS OF FREDERICAMYCIN". . p. 2181 - 2182. Retrieved 1985.
• 2、 Budny, Marcin,W?odarczyk, Joanna,Muzio?, Tadeusz,Bosiak, Mariusz Jan,Wolan, Andrzej. "Stereoselective synthesis of two potential metabolites of cis-metconazole". . p. 4285 - 4288. Retrieved 2017.
• 3、 Lopchuk, Justin M.,Green, Ilene L.,Badenock, Jeanese C.,Gribble, Gordon W.. "A short, protecting group-free total synthesis of bruceollines D, E, and J". . p. 4485 - 4487. Retrieved 2013.
• 4、 Gu, Yue-Qing,Zhang, Peng-Peng,Fu, Jun-Kai,Liu, Song,Lan, Yu,Gong, Jian-Xian,Yang, Zhen. "Regio- and Stereoselective Syntheses of 7-Oxabicyclo[2.2.1]heptanes via a Gold(I)-Catalyzed Cycloisomerization of Alkynediols: Asymmetric Total Synthesis of Farnesiferol C". supporting information. p. 1392 - 1397. Retrieved 2016/05/19.