22526-24-5

Usage

Physical state

Colorless to pale yellow liquid

Usage

Photoinitiator in ultraviolet (UV) curable inks, coatings, and adhesives

Photoinitiator type

Type II

InChI:InChI=1/C12H16O2/c1-12(2,3)11(13)9-7-5-6-8-10(9)14-4/h5-8H,1-4H3

Upstream product

• 79722-73-9 2-<<2,2-dimethyl-1-(2-methoxyphenyl)propylidene>amino>-2,4,4-trimethylpentane 
• 578-57-4 2-bromoanisole 
• 594-19-4 tert.-butyl lithium 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 3282-30-2 pivaloyl chloride 
• 86487-17-4 2-tri-n-butylstannylanisole 
• 1033260-24-0 C₂₆H₂₃NO₂Si 
• 558-17-8 tert-Butyl iodide 
• 100-66-3 methoxybenzene 
• 71146-29-7 pentamethylpivalophenone 

Downstream Products

• 676593-28-5 1-(2-isopropenylphenyl)-2,2-dimethylpropan-1-one 
• 2041-37-4 2,2-dimethyl-1-(o-tolyl)propan-1-one 
• 53847-36-2 α-(tert-butyl)-2-methoxyphenylmethanol 
• 16670-59-0 2-neopentylphenol 
• 328233-91-6 1-methoxy-2-neopentylbenzene 

Relevant academic research and scientific papers

A Fast and General Route to Ketones from Amides and Organolithium Compounds under Aerobic Conditions: Synthetic and Mechanistic Aspects

We report that the nucleophilic acyl substitution reaction of aliphatic and (hetero)aromatic amides by organolithium reagents proceeds quickly (20 s reaction time), efficiently, and chemoselectively with a broad substrate scope in the environmentally responsible cyclopentyl methyl ether, at ambient temperature and under air, to provide ketones in up to 93 % yield with an effective suppression of the notorious over-addition reaction. Detailed DFT calculations and NMR investigations support the experimental results. The described methodology was proven to be amenable to scale-up and recyclability protocols. Contrasting classical procedures carried out under inert atmospheres, this work lays the foundation for a profound paradigm shift of the reactivity of carboxylic acid amides with organolithiums, with ketones being straightforwardly obtained by simply combining the reagents under aerobic conditions and with no need of using previously modified or pre-activated amides, as recommended.

Chiral phosphoric acid catalyzed asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane

An asymmetric transfer hydrogenation of bulky aryl ketones with ammonia borane was successfully realized with chiral phosphoric acid (CPA) as catalyst and water as additive. A variety of optically active secondary alcohols were obtained in good to high yi

Synthesis of Functionalized Ketones from Acid Chlorides and Organolithiums by Extremely Fast Micromixing

Synthesis of ketones containing various functional groups from acid chlorides bearing electrophilic functional groups and functionalized organolithiums was achieved using a flow microreactor system. Extremely fast mixing is important for high chemoselectivity.

Synthesis of sterically hindered ketones from aldehydes via O-silyl oximes

A mild and efficient method to synthesize sterically hindered ketones from aldehydes via O-silyl oximes was developed. Treatment of O-triphenylsilylated oximes with alkyl iodides in the presence of triethyl borane afforded the corresponding ketones.

Catalyst-free alkanoylation of aromatic rings via arylstannanes. Scope and limitations

The reaction of alkanoyl chlorides with arylstannanes in 1,2-dichlorobenzene (180 °C) is a simple and direct route for the catalyst-free and regioselective synthesis of tertiary alkyl aryl ketones in good to excellent isolated yields (55-77%). Nevertheles

Enantioselective hydrogenation and transfer hydrogenation of bulky ketones catalysed by a ruthenium complex of a chiral tridentate ligand

A study on the enantioselective hydrogenation of tertiary alkyl ketones catalysed by a novel class of tridentate-Ru complex is reported. In contrast to the extensively studied [RuCl2(diphos)(di-primary amine)] complexes, this new class of hydro

Trifluoroacetic Acid-catalysed Transacylation of Arenes by Acylpentamethylbenzene

Facile transacylation between acylpentamethylbenzene and activated arenes such as anisole was found to occur in boiling trifluoroacetic acid (TFA).The mechanism for the transacylation between acetylpentamethylbenzene (AcPMB) and anisole with TFA was elucidated by means of product isolation and kinetics.The reaction proceeds via reversible protodeacetylation of AcPMB involving an ipso-protonated intermediate B to give pentamethylbenzene and acetic trifluoroacetic anhydride followed by irreversible acetylation of anisole by the mixed anhydride.The mechanism resulting in an ipso-protonated intermediate B was deduced from the reaction of acetylmesitylene with TFA as well as from the rate of deacetylation of 3,5-dideuterioacetylmesitylene with TFA.The formation of such an intermediate was also independently confirmed by 13C n.m.r. spectroscopic syudies on AcPMB in superacid solutions under stable conditions.

Metallo Aldimines. 3. Coupling of Lithium Aldimines with Aryl, Vinyl, and Acetylenic Halides

tert-Butyllithium aldimine, an acyl anion equivalent derived from 1,1,3,3-tetramethylbutyl isocyanide (TMBI) and tert-butyllithium, couples with aryl, vinyl, and acetylenic halides to give the corresponding ketimine which upon hydrolysis affords the corresponding ketones.These coupling reactions appear to result from halogen-metal exchange followed by addition-elimination to give the observed products.