14376-79-5

Basic information

• Product Name: 3,3,5,5-TETRAMETHYLCYCLOHEXANONE
• Synonyms: 3,3,5,5-TETRAMETHYLCYCLOHEXANONE;3,3,5,5-Tetramethyl-1-cyclohexanone;3,3,5,5-Tetramethylcyclohexanone,98%;NSC 91511;3,3,5,5-TetraMethylcyclohexanone 98%;3,3,5,5-tetramethylcyclohexan-1-one
• CAS NO: 14376-79-5
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 238-350-3
• Product Categories: API intermediates;C10;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 14376-79-5.mol
• Article Data: 31

Chemical Properties

• Melting Point: 11-12 °C
• Boiling Point: 200-203 °C
• Flash Point: 164 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 0.881 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.457mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1237421
• CAS DataBase Reference: 3,3,5,5-TETRAMETHYLCYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,5,5-TETRAMETHYLCYCLOHEXANONE(14376-79-5)
• EPA Substance Registry System: 3,3,5,5-TETRAMETHYLCYCLOHEXANONE(14376-79-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 14376-79-5(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to slightly yellow liquid

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 3463, 1984 DOI: 10.1016/S0040-4039(01)91048-2

Purification Methods

Purify the ketone first through a 24inch column packed with Raschig rings, then a 40cm Vigreux column (p 11) under reduced pressure (b 69-69.3o/7mm, see above). The oxime has m 144-145o (from 60% EtOH), and the semicarbazone has m 196-197o, 197-198o (214.5o, 217-218o) [Karasch & Tawney J Am Chem Soc 63 2308 1941, UV: Sandris & Ourisson Bull Soc Chim Fr 958 1956]. [Beilstein 7 III 163, 7 IV 89.]

InChI:InChI=1/C10H18O/c1-9(2)5-8(11)6-10(3,4)7-9/h5-7H2,1-4H3

Upstream product

• 917-64-6 methyl magnesium iodide 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 2650-40-0 3,3,5,5-tetramethyl cyclohexanol 
• 676-58-4 methylmagnesium chloride 
• 17530-69-7 3-chloro-5,5-dimethylcyclohex-2-en-1-one 
• 56671-85-3 5,5-dimethyl-3-iodocyclohex-2-en-1-one 
• 13271-49-3 3-bromo-5,5-dimethlycyclohex-2-en-1-one 
• 74-88-4 methyl iodide 
• 16393-75-2 1,3,3-Trimethyl-bicyclo<4.1.0>heptanon-(5) 
• 75-77-4 chloro-trimethyl-silane 
• 75-16-1 methylmagnesium bromide 
• 16393-75-2 (1R,6R)-4,4,6-Trimethyl-bicyclo[4.1.0]heptan-2-one 
• 42449-09-2 3.3.5.5-Tetramethylcyclohexanon-p-tosylhydrazon 
• 15681-48-8 lithium dimethylcuprate 

Downstream Products

• 78052-01-4 hydroxymethylene-2 tetramethyl-3,3,5,5 cyclohexanone-1 
• 38490-33-4 1,3,3,5,5-pentamethylcyclohexanol 
• 2650-40-0 3,3,5,5-tetramethyl cyclohexanol 
• 2065-77-2 2-bromo-3,3,5,5-tetramethylcyclohexanone 
• 28044-68-0 2r,6c-dibromo-3,3,5,5-tetramethyl-cyclohexanone 
• 2065-76-1 (+/-)-2r,6t-dibromo-3,3,5,5-tetramethyl-cyclohexanone 
• 99174-12-6 2,2,6-tribromo-3,3,5,5-tetramethyl-cyclohexanone 
• 14090-23-4 1,1,3,3-tetramethyl-5-methylenecyclohexane 
• 100315-25-1 2-Acetoxy-3,3,5,5-tetramethyl-cyclohexanon 
• 100874-28-0 2,6-Diacetoxy-3,3,5,5-tetramethyl-cyclohexanon-⁽¹⁾ 
• 64637-01-0 2-hydroxy-4,4,6,6-tetramethylcyclohex-2-enone 
• 29124-41-2 1,1-Difluor-3,3,5,5-tetramethyl-cyclohexan 
• 66323-36-2 1-Chlor-3,3,5,5-tetramethylcyclohex-1-en 
• 143586-27-0 1-Trimethylsilyloxy-3,3,5,5-tetramethylcyclohexene 

Relevant articles and documents

Nickel-catalysed conjugate addition to trimethylaluminum to sterically hindered α,β-unsaturated ketones

Nickel acetylacetonate is an efficient catalyst for the 1,4-addition of trimethylaluminum to α,β-unsaturated ketones. The reaction is strongly solvent dependent and gives best results in tetrahydrofuran or ethyl acetate. The reaction is especially useful for the nucleophilic 1,4-methyl transfer to sterically hindered enones. A β-cuparenone synthesis via conjugate methyl group addition to an enone precursor is described.

STREIC EFFECTS ON REACTION RATES II: RATE AND EQUILIBRIUM CONSTANTS FOR OXIDATION OF BICYCLIC ALCOHOLS

Equilibrium constants for oxidation of a series of bicyclic alcohols with cyclohexanone have been determined under Meerwein-Pondorf conditions.The data provide the thermodynamic background for interpretation of the mechanism of alcohol oxidation and ketone reductions.Free energies of the equilibrium (ΔGox) are compared with values calculated by molecular mechanics.

METHOD OF PREPARING 3,3,5,5-TETRAMETHYLCYCLOHEXANONE

Method of preparing 3,3,5,5-tetramethylcyclohexanone comprising step (i): (i) converting isophorone to 3,3,5,5-tetramethylcyclohexanone in the presence of methylmagnesium chloride. The thus prepared 3,3,5,5-tetramethylcyclohexanone may be employed in a method of preparing 1-amino-1,3,3,5,5-pentamethylcyclohexane (Neramexane) or a pharmaceutically acceptable salt thereof.

METHOD OF PREPARING NERAMEXANE

Method of preparing 1-amino-1,3,3,5,5-pentamethylcyclohexane or a pharmaceutically acceptable salt thereof, comprising at least two steps selected from the following steps (i) to (iv): (i) converting isophorone to 3,3,5,5-tetramethylcyclohexanone in the presence of methylmagnesium chloride; (N) converting 3,3,5,5-tetramethylcyclohexanone to 1-hydroxy-1,3,3,5,5- pentamethylcyclohexane in the presence of methylmagnesium chloride; (iii) converting 1-hydroxy-1,3,3,5,5-pentamethylcyclohexane to 1-chloroacetamido- 1,3,3,5,5-pentamethylcyclohexane in the presence of chloroacetonitrile in acidic solution; (iv) converting 1-chloroacetamido-1,3,3,5,5-pentamethylcyclohexane to 1-amino- 1,3,3,5,5-pentamethylcyclohexane in the presence of thiourea in water.