5064-52-8

Basic information

• Product Name: Cyclohexanone, 4-(1,1-dimethylethyl)-2-methyl-
• Synonyms: 4-tert-Butyl-2-methyl-cyclohexanon;4-tert-butyl-2-methyl-cyclohexanone;2-methyl-4-tert-butylcyclohexanone
• CAS NO: 5064-52-8
• Molecular Formula: C11H20O
• Molecular Weight: 168.279
• Mol File: 5064-52-8.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: Cyclohexanone, 4-(1,1-dimethylethyl)-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanone, 4-(1,1-dimethylethyl)-2-methyl-(5064-52-8)
• EPA Substance Registry System: Cyclohexanone, 4-(1,1-dimethylethyl)-2-methyl-(5064-52-8)

Safety Data

• Hazardous Substances Data: 5064-52-8(Hazardous Substances Data)

Usage

General Description

Cyclohexanone, 4-(1,1-dimethylethyl)-2-methyl-, is a chemical compound that belongs to the family of cyclohexanones. It is also known by its IUPAC name 4-tert-butyl-2-methylcyclohexanone. This chemical is commonly used as an intermediate in the synthesis of various compounds, including pharmaceuticals, agrochemicals, and fragrances. It is a colorless liquid with a faint odor, and it is soluble in organic solvents. 4-tert-butyl-2-methylcyclohexanone has several industrial applications, including in the production of plasticizers, resins, and rubber chemicals, as well as in the formulation of coatings and adhesives. It is important to handle this chemical with care, as it can be harmful if ingested, inhaled, or comes into contact with the skin.

Upstream product

• 80516-56-9 N-(4-tert-butylcyclohexylidene)cyclohexylamine 
• 74-88-4 methyl iodide 
• 98-27-1 2-Methyl-4-t-butylphenol 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 58911-63-0 4-tert-butylcyclohexanone dimethylhydrazone 
• 4147-00-6 4-tert-butyl-1-(1-pyrrolidinyl)cyclohexene 
• 19980-19-9 4-t-butyl-1-trimethylsilyloxy-1-cyclohexene 
• 68823-73-4 C₁₃H₂₅N 
• 87373-03-3 trans-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylic acid 
• 87373-02-2 cis-5-tert-butyl-1-methyl-2-oxocyclohexanecarboxylic acid 
• 3211-27-6 4-tert-butyl-2-methylcyclohexanone 
• 58911-80-1 trans-4-tert-Butyl-2-methyl-cyclohexanone-N,N-dimethylhydrazone 
• 7360-39-6 1-acetoxy-4-tert-butylcyclohexene 
• 43131-76-6 (C₄H₉)3SnO(C₆H₈C₄H₉) 

Downstream Products

• 86459-81-6 2-acetyl-2-methyl-4-t-butylcyclohexanone 
• 10347-88-3 2-tert-butyl-1,4-butanedicarboxylic acid 
• 5581-94-2 3-tert-Butyl-cyclopentanone 
• 88828-77-7 1,2-Dimethyl-4-tert.-butyl-cyclohex-1-en 
• 21862-63-5 trans-4-tert-butylcyclohexanol 
• 2484-73-3 trans-4-tert-butyl-cis-2-methylcyclohexanol 
• 2484-73-3 cis-4-tert-butyl-trans-2-methylcyclohexanol 
• 2484-73-3 trans-4-tert-butyl-trans-2-methylcyclohexanol 
• 3211-27-6 4-tert-butyl-2-methylcyclohexanone 
• 32383-54-3 1-methyl-trans-2-methyl-cis-4-t-butylcyclohexanol 
• 32383-54-3 1-methyl-cis-2-methyl-trans-4-t-butylcyclohexanol 
• 86137-12-4 (4R,6S)-4-tert-Butyl-2-hydroxy-6-methyl-6-(2-methyl-allyl)-cyclohex-2-enone 
• 86137-12-4 (4S,6S)-4-tert-Butyl-2-hydroxy-6-methyl-6-(2-methyl-allyl)-cyclohex-2-enone 
• 86137-11-3 (4R,6R)-6-Allyl-4-tert-butyl-2-hydroxy-6-methyl-cyclohex-2-enone 

Relevant articles and documents

Hydrogen shifts in cyclohexylcarbenes. Spatial dependence of activating power and of primary deuterium isotope effects

The conformationally biased ketones 4-t-butyl-cis-2-methylcyclohexanone (1c) and 4-t-butyl-cis-2-trans-6-dimethylcyclohexanone (7a; and its 2,6-dideuterio derivative 7c) were converted into p-toluenesulfonylhydrazone Li salts. Thermolysis or photolysis generated putative singlet carbenes, which underwent competitive axial vs equatorial H shift (or D shift in the case of 7c) to give alkenes. Product analysis showed that a bystander Me(eq) substituent promotes a geminal H shift several times more efficiently than does a bystander Me(ax). This geometry-dependent activating power parallels behavior noted earlier for OMe and Ph bystander groups; but as Me groups are rotationally symmetric and possess no lone pair or π electrons this phenomenon cannot be attributed solely to rotameric considerations or to effects involving mobile electron clouds. For the trans-dimethylcarbenes 10a and 10c the primary deuterium isotope effect (k(H)/k(D)) for axial migration (I(ax)) was determined to be ca. 1.5 times larger than that for equatorial migration (I(eq)). This finding invalidates the common assumption that I(ax) = I(eq) and suggests that published data on deuterium isotope effects and on H(ax)/H(eq) migration selectivities need to be adjusted.

Axial/equatorial proportions for 2-substituted cyclohexanones

Axial-equatorial conformational proportions have been measured for 2- substituted cyclohexanones in chloroform by the Eliel method for F, Cl, Br, I, MeO, MeS, Me2N, MeSe, and Me. For the first seven of these, at least five experimentally independent measurables were used and the resulting conformational preferences appear to be accurate to within 10%. Systematic errors degraded the results for MeSe and Me. For Me2N, the conformational preference also was measured for the first time at slow exchange in the low- temperature 13C spectrum in several solvents. In chloroform, steric and polar effects contribute to the conformational preferences, with steric effects dominant for large groups such as I and MeS.

Alkyl Migration in Competition with Phenylthio Migration in the Acid-catalysed Rearrangement of Alcohols

Sulfonate derivatives of conformationally rigid syn-2-phenylthiocyclohexanols, which are prevented from phenylthio migration by stereochemistry, rearrange slowly by alkyl migration or ring contraction.In contrast to other electronegative groups, phenylthio slows the reaction down but allows migration of other groups.