2,2,5-Trimethylcyclopentanone

Base Information

• Chemical Name: 2,2,5-Trimethylcyclopentanone
• CAS No.: 4573-09-5
• Molecular Formula: C8H14O
• Molecular Weight: 126.199
• Hs Code.: 2914299000
• NSC Number: 179392
• DSSTox Substance ID: DTXSID301347808
• Nikkaji Number: J504.853B
• Mol file: 4573-09-5.mol

Synonyms:2,2,5-Trimethylcyclopentanone;4573-09-5;2,2,5-trimethylcyclopentan-1-one;Cyclopentanone, 2,2,5-trimethyl-;NSC179392;2,5-Trimethylcyclopentanone;Cyclopentanone,2,5-trimethyl-;SCHEMBL2691519;2,2,5-Trimethyl cyclopentanone;1.1.3-Trimethylcyclopentanon-2;DTXSID301347808;MFCD00049165;AKOS006283776;NSC 179392;NSC-179392;FT-0691314;3-(5-Cyano-2-hydroxy-1,4-dimethyl-6-oxo-1,6-dihydropyridin-3-ylazo)benzenesulfonicacid

Chemical Property of 2,2,5-Trimethylcyclopentanone

Chemical Property:

• Vapor Pressure: 3.57mmHg at 25°C
• Refractive Index: 1.431
• Boiling Point: 152 °C at 760 mmHg
• Flash Point: 45.4 °C
• PSA: 17.07000
• Density: 0.878 g/cm³
• LogP: 2.01160
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 126.104465066
• Heavy Atom Count: 9
• Complexity: 136

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Ketones (
• Canonical SMILES: CC1CCC(C1=O)(C)C

Technology Process of 2,2,5-Trimethylcyclopentanone

There total 9 articles about 2,2,5-Trimethylcyclopentanone 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: 79.0%

1-(trimethylsilyloxy)cyclopentene (19980-43-9) + methyl iodide (74-88-4) → 2-Methylcyclopentanone (1120-72-5) + 2,2-dimethylcyclopentanone (4541-32-6) + 2,2,5-trimethylcyclopentanone (4573-09-5) + cis-2,5-dimethylcyclopentanone (6672-39-5)

Guidance literature:

With methyllithium; In tetrahydrofuran; at 0 ℃; for 3h; Further byproducts given;

DOI:10.1021/jo00269a006

Reference yield: 79.0%

1-(trimethylsilyloxy)cyclopentene (19980-43-9) + methyl iodide (74-88-4) → 2-Methylcyclopentanone (1120-72-5) + 2,2-dimethylcyclopentanone (4541-32-6) + 2,2,5-trimethylcyclopentanone (4573-09-5) + cis-2,5-dimethylcyclopentanone (6672-39-5) + (+/-)-trans-2,5-dimethylcyclopentanone (83664-37-3)

Guidance literature:

With methyllithium; In tetrahydrofuran; at 0 ℃; for 3h; Product distribution; var. temp., times, and reagent systems; other lithium enolates;

DOI:10.1021/jo00269a006

Reference yield:

(1E)-N-tert-butyl-2,2-dimethylcyclopentanimine + methyl iodide (74-88-4) → 2,2-dimethylcyclopentanone (4541-32-6) + 2,2,5-trimethylcyclopentanone (4573-09-5)

Guidance literature:

(1E)-N-tert-butyl-2,2-dimethylcyclopentanimine; With methyllithium; diisopropylamine; In tetrahydrofuran; diethyl ether; at 42 ℃; for 2h;

methyl iodide; In tetrahydrofuran; diethyl ether; at 0 ℃;

With sulfuric acid; In water; at 130 ℃; for 1h; regioselective reaction;

DOI:10.1002/hlca.201800037

upstream raw materials:

1-(trimethylsilyloxy)cyclopentene

methyl iodide

2-Methylcyclopentanone

N-tert-butylcyclopentanimine

Downstream raw materials:

2,2-dimethylsuccinic acid

3-fluoro-N-((2,5,5-trimethylcyclopent-1-enyl)methyl)aniline hydrochloride

3-fluoro-N-((2,5,5-trimethylcyclopent-1-enyl)methyl)aniline

1-fluoro-3-((2,5,5-trimethylcyclopent-1-enyl)methoxy)benzene

Refernces

• 1、 Quesnel, Yannick,Bidois-Sery, Laure,Poirier, Jean-Marie,Duhamel, Lucette. "Highly regioselective alkylation at the more hindered α-site of unsymmetrical ketones by use of their potassium enolates. A comparative study with lithium enolates". . p. 413 - 415. Retrieved 2007/10/03.