2040-21-3

Usage

Chemical Class

Ketone

Physical State

Colorless, flammable liquid

Odor

Strong, sweet

Uses

Intermediate in the synthesis of pharmaceuticals and perfumes, solvent in industrial applications

Health Risks

Harmful if ingested or inhaled, should be minimized to prevent adverse health effects

Upstream product

• 16620-71-6 isopropyl o-tolyl ketimine 
• 68020-95-1 2-benzyloxy-3-methyl-butyronitrile 
• 79-30-1 isobutyryl chloride 
• 108-88-3 toluene 
• 79-31-2 isobutyric Acid 
• 529-20-4 2-methylphenyl aldehyde 
• 100-44-7 benzyl chloride 
• 67-56-1 methanol 
• 577-16-2 2-Methylacetophenone 
• 75-24-1 trimethylaluminum 
• 611-70-1 phenyl isopropyl ketone 
• 1068-55-9 isopropylmagnesium chloride 
• 933-88-0 ortho-toluoyl chloride 
• 2040-14-4 2-methylpropiophenone 

Downstream Products

• 155225-03-9 4-Ethyl-3-hydroxy-2,2-dimethyl-1-o-tolyl-hexan-1-one 
• 155225-09-5 3-Hydroxy-2,2-dimethyl-1-o-tolyl-butan-1-one 
• 155225-08-4 3-Hydroxy-2,2-dimethyl-1-o-tolyl-pentan-1-one 
• 100994-08-9 C₁₅H₂₀O₂ 
• 1370713-49-7 1-[4-(1-ethoxy-2,2,2-trifluoro-1-trimethylsiloxyethyl)-2-methylphenyl]-2-methylpropan-1-one 
• 1251902-40-5 2-methyl-1-(2-methyl-4-trifluoroacetylphenyl)propan-1-one 
• 100994-03-4 1-o-methylphenyl-2-methylpropanol 
• 54090-91-4 N-(2-methylbenzoyl)-S-methyl-S-phenyl sulfoximine 
• 1583276-61-2 (E)-2,2-dimethyl-5-phenyl-1-(o-tolyl)pent-4-en-1-one 
• 1583276-22-5 2-benzyl-4,4-dimethyl-3,4-dihydro-2H-pyrrole 1-oxide 
• 1583276-45-2 (1Z,4E)-2,2-dimethyl-5-phenyl-1-(o-tolyl)pent-4-en-1-one oxime 
• 134298-67-2 1-cyclohexyl-2-(1'-hydroxy-1',2'-dihydrobenzocyclobuten-1'-yl)-2-methylpropan-1-one 
• 134298-59-2 1-cyclohexyl-2,2-dimethyl-3-(o-methylphenyl)propane-1,3-dione 
• 134298-73-0 3-cyclohexyl-3-hydroxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one 

Relevant academic research and scientific papers

The effect of type of acid sites in molecular sieves on activity and selectivity in acylation reactions

The role of the type of acid site (Broensted vs. Lewis) on the activity and selectivity of molecular sieve catalysts was investigated in ferrocene and toluene acylation. H-, Zn-, Fe-, Aland La-forms of zeolite Beta, USY and mesoporous molecular sieves (A1

Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol

One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.

Experimental and Computational Studies of Palladium-Catalyzed Spirocyclization via a Narasaka-Heck/C(sp3or sp2)-H Activation Cascade Reaction

The first synthesis of highly strained spirocyclobutane-pyrrolines via a palladium-catalyzed tandem Narasaka-Heck/C(sp3 or sp2)-H activation reaction is reported here. The key step in this transformation is the activation of a δ-C-H bond via an in situ generated σ-alkyl-Pd(II) species to form a five-membered spiro-palladacycle intermediate. The concerted metalation-deprotonation (CMD) process, rate-determining step, and energy barrier of the entire reaction were explored by density functional theory (DFT) calculations. Moreover, a series of control experiments was conducted to probe the rate-determining step and reversibility of the C(sp3)-H activation step.

Manganese catalyzed α-methylation of ketones with methanol as a C1 source

The direct α-methylation of ketones with methanol under hydrogen borrowing conditions using a well-defined manganese PN3P complex as a pre-catalyst was, for the first time, achieved. The reactions typically proceed at 120 °C for 20 h with 3 mol% pre-catalyst loading and in the presence of NaOtBu (50 mol%) as base. The scope of the reaction was extended to the α-methylation of esters.

α-Methylation of Ketones with Methanol Catalyzed by Ni/SiO2-Al2O3

α-Methylation of ketones with methanol catalyzed by a cheap and easy to handle Ni/SiO2-Al2O3 was explored. After optimization of the reaction between propiophenone and methanol, the desired product was obtained in 95 % isolated yield. A wide range of ketones was methylated under the optimized conditions (16 examples). This procedure was extended to a three-component cross-benzylation-methylation of acetophenone.

Iron-Catalyzed Methylation Using the Borrowing Hydrogen Approach

A general iron-catalyzed methylation has been developed using methanol as a C1 building block. This borrowing hydrogen approach employs a Kn?lker-type (cyclopentadienone)iron carbonyl complex as catalyst (2 mol %) and exhibits a broad reaction scope. A variety of ketones, indoles, oxindoles, amines, and sulfonamides undergo mono- or dimethylation in excellent isolated yields (>60 examples, 79% average yield).

Syndiotactic Poly(aminostyrene)-Supported Palladium Catalyst for Ketone Methylation with Methanol

Palladium nanoparticles immobilized on an amino-functionalized syndiotactic polystyrene (sPS-N) served as a novel recyclable catalyst for the dimethylation and cross methyl alkylation of a wide range of ketones with methanol as the methylation agent. This heterogeneous catalyst (Pd@sPS-N) was highly robust and showed excellent thermal stability and chemical resistance. It not only showed remarkably high activity, but it could also be easily recovered by filtration without loss of activity.

Methylation of C(sp3)-H/C(sp2)-H bonds with methanol catalyzed by cobalt system

A highly efficient Co-based catalytic system, composed of a commercially available Co salt, a tetradentate phosphine ligand P-(CH2CH2PPh2)3(PP3), and a base (denoted as [Co]/PP3/base), is developed for the methylation of C(sp3)-H and C(sp2)-H bonds using methanol as a methylating reagent. The Co(BF4)2.6H2O/PP3/K2CO3 catalytic system showed high catalytic activity for the methylation of C-H bonds in aryl alkyl ketones, aryl acetonitriles, and indoles, with wide substrate scope and good functional group tolerance, and methylsubstituted products were obtained in good to excellent yields at 100 °C. This cheap, readily available, and highly efficient Co-based catalytic system may have promising applications in methylation reaction using methanol.

Iron-Catalyzed Ortho C-H Methylation of Aromatics Bearing a Simple Carbonyl Group with Methylaluminum and Tridentate Phosphine Ligand

Iron-catalyzed C-H functionalization of aromatics has attracted widespread attention from chemists in recent years, while the requirement of an elaborate directing group on the substrate has so far hampered the use of simple aromatic carbonyl compounds such as benzoic acid and ketones, much reducing its synthetic utility. We describe here a combination of a mildly reactive methylaluminum reagent and a new tridentate phosphine ligand for metal catalysis, 4-(bis(2-(diphenylphosphanyl)phenyl)phosphanyl)-N,N-dimethylaniline (Me2N-TP), that allows us to convert an ortho C-H bond to a C-CH3 bond in aromatics and heteroaromatics bearing simple carbonyl groups under mild oxidative conditions. The reaction is powerful enough to methylate all four ortho C-H bonds in benzophenone. The reaction tolerates a variety of functional groups, such as boronic ester, halide, sulfide, heterocycles, and enolizable ketones.

C-C coupling of ketones with methanol catalyzed by a N-heterocyclic carbene-phosphine iridium complex

An N-heterocyclic carbene-phosphine iridium complex system was found to be a very efficient catalyst for the methylation of ketone via a hydrogen transfer reaction. Mild conditions together with low catalyst loading (1 mol%) were used for a tandem process which involves the dehydrogenation of methanol, C=C bond formation with a ketone, and hydrogenation of the new generated double bond by iridium hydride to give the alkylated product. Using this iridium catalyst system, a number of branched ketones were synthesized with good to excellent conversions and yields.