3,3,5,5-Tetramethylcyclohexanone

Base Information

• Chemical Name: 3,3,5,5-Tetramethylcyclohexanone
• CAS No.: 14376-79-5
• Molecular Formula: C10H18O
• Molecular Weight: 154.252
• Hs Code.: 29142990
• European Community (EC) Number: 238-350-3
• NSC Number: 91511
• DSSTox Substance ID: DTXSID20162538
• Nikkaji Number: J142.889F
• Wikidata: Q72507543
• Mol file: 14376-79-5.mol

Synonyms:3,3,5,5-Tetramethylcyclohexanone;14376-79-5;3,3,5,5-tetramethylcyclohexan-1-one;Cyclohexanone, 3,3,5,5-tetramethyl-;3,3,5,5-Tetramethyl cyclohexanone;MFCD00001640;3,3,5,5-tetramethyl-cyclohexanone;EINECS 238-350-3;Cyclohexanone,3,3,5,5-tetramethyl-;NSC91511;SCHEMBL638075;3,5,5-Tetramethylcyclohexanone;DTXSID20162538;Cyclohexanone,3,5,5-tetramethyl-;NSC 91511;NSC-91511;RB3201;AKOS015906416;3,3,5,5-Tetramethyl-1-cyclohexanone;AM85584;CS-W008480;PB47843;3,3,5,5-tetramethyl-cyclohexan-1-one;3,3,5,5-Tetramethylcyclohexanone, 98%;AS-54429;SY039671;FT-0687855;EN300-96572;A884892;J-007870;Z1255415405

Chemical Property of 3,3,5,5-Tetramethylcyclohexanone

Chemical Property:

• Appearance/Colour: Clear colorless to slightly yellow liquid
• Vapor Pressure: 0.457mmHg at 25°C
• Melting Point: 11-12 °C
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 193.8 °C at 760 mmHg
• Flash Point: 73.3 °C
• PSA: 17.07000
• Density: 0.857 g/cm³
• LogP: 2.79180
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 154.135765193
• Heavy Atom Count: 11
• Complexity: 159

Purity/Quality:

97% ^*data from raw suppliers

3,3,5,5-Tetramethylcyclohexanone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CC(=O)CC(C1)(C)C)C

Technology Process of 3,3,5,5-Tetramethylcyclohexanone

There total 23 articles about 3,3,5,5-Tetramethylcyclohexanone 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: 96.0%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + trimethylaluminum (75-24-1) → 3,3,5,5-tetramethylcyclohexanone (14376-79-5)

Guidance literature:

With chloro-trimethyl-silane; copper(I) bromide; In tetrahydrofuran; hexane; for 4h;

Reference yield: 93.0%

methyl magnesium iodide (917-64-6) + chloro-trimethyl-silane (75-77-4) + 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 3,3,5,5-tetramethylcyclohexanone (14376-79-5) + 1-Trimethylsilyloxy-3,3,5,5-tetramethylcyclohexene (143586-27-0) + 3-Hydroxy-1,3,5,5-Tetramethylcyclohexen (94925-94-7)

Guidance literature:

With copper(I) iodide-lithium chloride; In tetrahydrofuran; at 0 ℃; for 0.5h; Product distribution; other α,β-unsaturated ketones and esters; other Grignard reagents; var. catalysts, var. temperatures;

DOI:10.1016/0022-328X(95)05699-P

Reference yield: 87.0%

3.3.5.5-Tetramethylcyclohexanon-p-tosylhydrazon (42449-09-2) → 3,3,5,5-tetramethylcyclohexanone (14376-79-5)

Guidance literature:

Envirocat EPZG; In water; acetone; at 80 ℃; for 4h;

DOI:10.1055/s-1997-5749

upstream raw materials:

3,5,5-Trimethylcyclohex-2-en-1-one

methylmagnesium bromide

ethanol

1-hydroxy-3,3,5,5-tetramethyl-cyclohexanecarbonitrile

Downstream raw materials:

1-Hydroxymethyl-3,3,5,5-tetramethyl-cyclohexanol

1-(1-Hydroxy-1-methyl-ethyl)-3,3,5,5-tetramethyl-cyclohexanol

1-ethyl,3,3,5,5-tetramethyl cyclohexanol

1-Trimethylsilyloxy-3,3,5,5-tetramethylcyclohexene

Refernces

Improved addition of phenyllithium to hindered ketones by the use of non-polar media

10.1016/S0040-4039(02)00597-X

The research focuses on the improved addition of phenyllithium (PhLi) to hindered ketones using non-polar media at room temperature. The study was conducted on six hindered ketones: (?)-fenchone, (?)-menthone, (+)-camphor, 3,3,5-trimethylcyclohexanone, 3,3,5,5-tetramethylcyclohexanone, and 2,4-dimethylpentan-3-one. The researchers aimed to enhance the low reactivity of these ketones towards PhLi, which traditionally yields modest results when performed in ethers like diethyl ether or THF. The experiments involved dissolving the ketones in a non-polar solvent, such as toluene or a toluene-diethyl ether mixture, and then slowly adding commercial PhLi via syringe. The mixtures were stirred at room temperature for 2 to 4 hours. The results showed significant improvements in yield compared to traditional methods, with the addition occurring in a stereospecific manner, favoring the less-hindered side. The configuration of the adducts was established using 13C NMR according to literature methods. This approach was found to be more efficient, cost-effective, and easier, offering a significant advantage for the synthesis of chiral inducers.