29097-52-7

Usage

Uses

Used in Chemical Industry:
2,2,4,4-Tetramethyl-3-pentanone imine is used as a key intermediate in the synthesis of various organic compounds, such as dyes and metabolites. Its stability and unique structure make it a valuable building block for the development of new molecules with potential applications in various fields.
Used in Pharmaceutical Industry:
2,2,4,4-Tetramethyl-3-pentanone imine is used as a starting material for the synthesis of pharmaceutical compounds. Its unique properties allow for the creation of novel drug candidates with potential therapeutic applications.
Used in Dye Industry:
2,2,4,4-Tetramethyl-3-pentanone imine is used as a precursor in the production of dyes. Its stability and reactivity make it an ideal candidate for the development of new dye molecules with improved properties, such as enhanced color intensity and stability.

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4527, 1971 DOI: 10.1021/ja00747a031

InChI:InChI=1/C9H19N/c1-8(2,3)7(10)9(4,5)6/h10H,1-6H3

Upstream product

• 630-18-2 tert-butyl isocyanide 
• 507-20-0 tertiary butyl chloride 
• 73996-71-1 2,2,4,4-tetramethylpentan-3-one-O-(phenylmethyl)oxime 

Downstream Products

• 56741-77-6 3,3’-di-tert-butyl oxaziridine 
• 33420-23-4 2,2,4,4-tetramethyl-pentan-3-one (toluene-4-sulfonyl)-hydrazone 
• 103708-90-3 N-(1-tert-Butyl-2,2-dimethylpropyliden)benzamid 
• 815-24-7 Di-t-butyl ketone 
• 56956-22-0 2,2,4,4-Tetramethylpentan-3-on-(triphenylphosphoranyliden)hydrazon 
• 54396-72-4 2,2-di-tert-butyl-5,5-diphenyl-2,5-dihydro-[1,3,4]thiadiazole 
• 54396-71-3 1,1-di-tert-butyl-2,2-diphenylethylene 
• 71996-42-4 (1-tert-Butyl-1-chloro-2,2-dimethyl-propyl)-(1-chloro-2,2,2-trifluoro-1-phenyl-ethyl)-carbodiimide 
• 71996-44-6 (1-tert-Butyl-1-chloro-2,2-dimethyl-propyl)-(1-chloro-2,2-dimethyl-1-phenyl-propyl)-carbodiimide 
• 118364-66-2 N-(2,4,6-trimethylphenyl)-4-bromobenzamide 
• 118364-63-9 (1-tert-Butyl-2,2-dimethyl-propylidene)-(2,2,2-trifluoro-1-isocyanato-1-phenyl-ethyl)-amine 
• 6846-12-4 4-bromo-N-phenyl-benzamide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 119208-78-5 (Z)-1,2-Bis(di-tert-butylmethylen)amino-1,2-diphenylethylen 

Relevant academic research and scientific papers

Thermal decomposition of O-benzyl ketoximes; role of reverse radical disproportionation

Thermolyses of seven dialkyl, two alkyl-aryl and two diaryl O-benzyl ketoxime ethers, R1R2C=NOCH2Ph, have been examined in three hydrogen donor solvents: tetralin, 9,10-dihydrophenanthrene, and 9,10-dihydroanthracene. All the oxime ethers gave the products expected from homolytic scission of both the O-C bond (viz., R1R2C=NOH and PhCH3) and N-O bond (viz., R1R2C=NH and PhCH2OH). The yields of these products depended on which solvent was used and the rates of decomposition of the O-benzyl oxime ethers were greater in 9,10-dihydrophenanthrene and 9,10-dihydroanthracene than in tetralin. These results indicated that a reverse radical disproportionation reaction in which a hydrogen atom was transferred from the solvent to the oxime ether, followed by β-scission of the resultant aminoalkyl radical, must be important in the latter two solvents. Benzaldehyde was found to be an additional product from thermolyses conducted in tetralin. This, and other evidence, indicated that another induced decomposition mode involving abstraction of a benzylic hydrogen atom, followed by β-scission of the resulting benzyl radical, became important for some substrates. Participation by minor amounts of enamine tautomers of the oxime ethers was shown to be negligible by comparison of thermolysis data for the O-benzyloxime of bicyclo[3.3.1]nonan-9-one, which cannot give an enamine tautomer, with that of the O-benzyloxime of cyclohexanone.

Sterically congested molecules, 16: A convenient synthesis of di-tert-butyl ketone via its imine, 2,2,4,4-tetramethyl-3-pentanimine

2,2,4,4-Tetramethyl-3-pentanimine (3) is efficiently prepared by a Barbier-type reaction of pivalonitrile (1) with an excess of tert-butyl chloride (2) and metallic lithium in ether. Its purification by extraction into aqueous acid and slow hydrolysis permit an inexpensive and very simple production of di-tert-butyl ketone (4). VCH Verlagsgesellschaft mbH, 1996.