3594-36-3

Usage

Chemical compound

Yes

Use

Flavoring agent in food and beverage production

Responsible for

Buttery flavor and aroma in certain food products

Examples of food products

Popcorn, margarine, and butter-flavored snacks

Health concerns

Linked to respiratory issues in workers at microwave popcorn and flavoring manufacturing factories

Efforts made

Limiting the use and concentration of diacetyl in food products due to health concerns

InChI:InChI=1/C17H16O2/c1-12-3-7-14(8-4-12)16(18)11-17(19)15-9-5-13(2)6-10-15/h3-10H,11H2,1-2H3

Upstream product

• 108-88-3 toluene 
• 1663-67-8 malonoyl dichloride 
• 94-08-6 4-methylbenzoic acid ethyl ester 
• 122-00-9 para-methylacetophenone 
• 874-60-2 4-methyl-benzoyl chloride 
• 123-54-6 acetylacetone 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 7446-70-0 aluminium trichloride 
• 104-87-0 4-methyl-benzaldehyde 
• 99-94-5 p-Toluic acid 
• 832737-81-2 2-chloro-1,3-bis(4′-methyl-phenyl)-1,3-propanedione 
• 97691-66-2 1,3-bis(4-methylphenyl)prop-2-yn-1-one 
• 62375-98-8 1,3-di(4-methylphenyl)propane-1,3-dione 
• 109-77-3 malononitrile 

Downstream Products

• 122-00-9 para-methylacetophenone 
• 3594-38-5 3,5-di-p-tolyl-2H-[1,2,6]thiadiazine 1,1-dioxide 
• 29574-59-2 1,3-Bis-<4-methyl-phenyl>-propantrion-(1,2,3) 
• 52046-56-7 2-bromo-1-(4-chlorophenyl)-3-phenylpropane-1,3-dione 
• 81798-03-0 [5-(4-Methyl-benzoyl)-4-phenyl-2-p-tolyl-1H-pyrrol-3-yl]-p-tolyl-methanone 
• 119097-66-4 p-Tolyl-(3-p-tolyl-2H-azirin-2-yl)-methanone 
• 81668-47-5 1-methyl-4,6-di-p-tolylpyrimidin-2(1H)-one 
• 155886-72-9 2,2-Dimethyl-1,3-bis(4'-methylphenyl)-1,3-propanedione 
• 167702-26-3 Dithio-bis-(di(4-toluyl)-methane) 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 5333-22-2 1,5-di-p-tolylpentane-1,5-dione 
• 170647-13-9 2,4-bis-(4-methylbenzoyl)-1,5-di-p-tolylpentane-1,5-dione 
• 99-94-5 p-Toluic acid 
• 257953-67-6 diethyl 3,4-bis(4-methylphenyl)thieno[2,3-b]thiophene-2,5-dicarboxylate 

Relevant academic research and scientific papers

Visible and Near-Infrared Emission from Lanthanoid β-Triketonate Assemblies Incorporating Cesium Cations

The reaction of the β-triketonate ligands tris(4-methylbenzoyl)methanide and tribenzoylmethanide with the trivalent lanthanoids Eu3+, Er3+, and Yb3+ in the presence of Cs+ afforded polymeric structures where the

A metal-free strategy for the cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol

Here, we report a metal-free approach for the construction of methylene-bridged bis-1,3-dicarbonyl compounds via cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol. In addition, we have extended this methodology to synthesize tetra-substituted pyridine derivatives using 1,3-dicarbonyl, 2-methoxyethanol and NH4OAc in one step. The key advantages include accepting a wide range of substrates, utilizing O2 as the sole oxidant, and synthesizing biologically active compounds such as 1,4-dihydropyridine and pyrazole. This journal is

PPh3-catalyzed β-selective addition of α-fluoro β-dicarbonyl compounds to allenoates

A highly selective phosphine-catalyzed β-addition of α-fluoro β-dicarbonyl compounds to allenoates has been developed. Both α-fluoro β-diketones and α-fluoro β-keto esters prove to be competent fluorocarbon nucleophiles, giving a series of the β-addition products bearing a fluorinated quaternary carbon center in good to excellent yields and with excellent regioselectivities. A plausible reaction pathway is presented.

Br?nsted acid-catalyzed enantioselective addition of 1,3-diones to in situ generated N-acyl ketimines

A Br?nsted acid-catalyzed asymmetric Mannich-type addition of 1,3-diones to cyclic N-acyl ketimines is reported for the synthesis of enantioenriched isoindolinones. Various dicarbonyl-substituted isoindolinones bearing a quaternary carbon stereocenter were synthesized with excellent yields (up to 98%) and moderate to high enantioselectivities (up to 95% ee), and most of them possess a fluorine atom at the reactive center. Furthermore, the synthetic utility of the protocol has been demonstrated by the debenzoylation of the product.

Ag-Catalyzed Insertion of Alkynyl Carbenes into C-C Bonds of β-Ketocarbonyls: A Formal C(sp2) Insertion

Here we report a silver-catalyzed alkynyl carbene insertion into β-ketocarbonyls using alkynyl N-nosylhydrazones as alkynyl carbene precursors, which provides access to trisubstituted allenyl ketones. This reaction represents the first example of an alkynyl carbene insertion into a C-C σ bond, affording products homologated with an sp2 carbon center. The products are useful substrates for further transformations. Experimental investigations and theoretical calculations suggest the reaction proceeds through a stepwise enol cyclopropanation/retro-aldol pathway.

Tris-(2-pyridylmethyl)amine-ligated Cu(II) 1,3-diketonate complexes: Anaerobic retro-Claisen and dehalogenation reactivity of 2-chloro-1,3-diketonate derivatives

We report synthetic, structural and reactivity investigations of tris-(2-pyridylmethyl)amine (TPA)-ligated Cu(ii) 1,3-diketonate complexes. These complexes exhibit anaerobic retro-Claisen type C-C bond cleavage reactivity which exceeds that found in analo

I2-Promoted [3+2] Cyclization of 1,3-Diketones with Potassium Thiocyanate: a Route to Thiazol-2(3H)-One Derivatives

An I2-promoted strategy has been developed for the synthesis of thiazol-2(3H)-one derivatives from 1,3-diketones with potassium thiocyanate. This [3+2] cyclization reaction involves C?S and C?N bond formation and exhibits good functional group tolerance. A series of thiazol-2(3H)-one derivatives are obtained in moderate to good yields. (Figure presented.).

Organocatalytic Asymmetric Cascade Michael-acyl Transfer Reaction between 2-Fluoro-1,3-diketones and Unsaturated Thiazolones: Access to Fluorinated 4-Acyloxy Thiazoles

Quinine derived bifunctional urea catalyzed cascade Michael-acyl transfer reaction of 5-alkenyl thiazolones and monofluorinated β-diketones has been developed. The fluorine containing 4-acyloxy thiazoles were synthesized in high yields and good diastereo-and excellent enantioselectivities. Synthetic transformations, including synthesis of 4-hydroxy thiazoles, have been demonstrated.

Method for synthesizing 1, 3-dicarbonyl compound based on terminal alkyne and acyl halide by one-pot process

The invention belongs to the technical field of catalytic synthesis, and discloses a method for synthesizing a 1, 3-dicarbonyl compound by a one-pot process, and the method comprises the following steps: by using simple palladium and copper salts as catalysts, reacting terminal alkyne with acyl halide at 0-80 DEG C for 0.5-12 hours under the action of trifluoromethanesulfonic acid to obtain the 1,3-dicarbonyl compound, wherein the molar ratio of the terminal alkyne to the acyl halide to the palladium salt to the copper salt to the trifluoromethanesulfonic acid is 1 to (1 to 2) to (0.00001 to0.10) to (0.00001 to 0.10) to (0.00004 to 0.40); the catalysts used in the method are common the commercialized palladium salt and copper salt, reagents used in the reaction are commercialized reagents, in addition, the raw materials are cheap and easy to obtain, functional group tolerance is good, reaction conditions are mild, operation is easy and convenient, and atom economy is high.

Direct synthesis of 2,3,5-trisubstituted pyrroles: via copper-mediated one-pot multicomponent reaction

We have developed a copper-mediated one-pot synthesis of 2,3,5-trisubstituted pyrroles from 1,3-dicarbonyl compounds and acrylates using ammonium acetate as a nitrogen source. The reaction achieves C-C and C-N bond formation and provides an efficient approach to access highly functionalized pyrroles without further raw material preparation. This method is operationally simple, compatible with a wide range of functional groups, and provides the target products in moderate to good yields. This journal is