13145-56-7

Basic information

• Product Name: 1,4-Butanedione, 1,4-bis(4-methylphenyl)-
• CAS NO: 13145-56-7
• Molecular Formula: C18H18O2
• Molecular Weight: 266.34
• Mol File: 13145-56-7.mol

Chemical Properties

• CAS DataBase Reference: 1,4-Butanedione, 1,4-bis(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Butanedione, 1,4-bis(4-methylphenyl)-(13145-56-7)
• EPA Substance Registry System: 1,4-Butanedione, 1,4-bis(4-methylphenyl)-(13145-56-7)

Safety Data

• Hazardous Substances Data: 13145-56-7(Hazardous Substances Data)

Usage

Physical State

Yellow liquid

Odor

Strong, sweet, and fruity

Natural Occurrence

Commonly found in fruits such as berries and cherries

Primary Uses

a. Production of fragrances and flavorings
b. Intermediate in organic synthesis
c. Raw material for the production of pharmaceuticals and pesticides

Toxicity

Low toxicity, making it relatively safe for use in consumer products and industrial applications

Upstream product

• 42289-03-2 (Z)-1,4-Bis(4-methylphenyl)but-2-ene-1,4-dione 
• 543-20-4 succinoyl dichloride 
• 108-88-3 toluene 
• 13581-83-4 ω-(Methylsulphinyl)-p-methylacetophenon 
• 15982-67-9 1,4-di-p-tolyl-butane-1,4-diol 
• 77-77-0 Divinyl sulfone 
• 104-87-0 4-methyl-benzaldehyde 
• 122-00-9 para-methylacetophenone 
• 4209-24-9 p-methylphenacyl chloride 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 15229-65-9 α-Dimethylamino-α-(4-methylphenyl)-acetonitrile 
• 19832-78-1 1-(4-methylphenyl)prop-2-en-1-one 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 21399-23-5 2,5-di(4-methylphenyl)-1H-pyrrole 
• 57196-75-5 2,5-bis(p-tolyl)furan 
• 82366-98-1 2,5-bis(4'-methylphenyl)thiophene 
• 7568-23-2 1,4-di-p-tolylbutane 
• 5465-41-8 ditoluylethylene 
• 222158-46-5 C₂₂H₂₆ 
• 222158-41-0 C₂₂H₂₆ 
• 222158-45-4 C₂₂H₂₆ 
• 99-94-5 p-Toluic acid 
• 1189240-14-9 (-)-(1S,4S)-1,4-di(4-methylphenyl)-1,4-butanediol 
• 1205612-20-9 2,5-di-p-tolyl-N-[2-(benzylamino)phenyl]pyrrole 
• 1205612-05-0 2,5-di-p-tolyl-N-(2-mercaptophenyl)pyrrole 
• 51678-13-8 2,5-di-p-toluoylselenophene 

Relevant articles and documents

Unexpected formation of 4,4-dimethyl-1,2-disubstituted-dicarbonyl cyclopentanes from ketone enolate anions and 1,3-diiodo-2,2-dimethylpropane

Cyclic 1,4-dicarbonyl compounds can be easily obtained by mixing a solution of aryl methyl or alkyl methyl ketone enolate anions with 1,3-diiodo-2,2-dimethylpropane in DMSO. This represents the first example of dimerization of ketone enolate anions using a simple diiodoalkane as a reagent followed by subsequent double alkylation with bis-iodide yielding a cyclopentane adduct. This methodology allows the use of a simple potassium tert-butoxide as a base at room temperature for the formation of three C-C bonds resulting in a relatively complex five-membered ring diketone structure under transition-metal-free conditions.

Novel photo-rearrangement of 1,5-di(p-methoxyphenyl)-6,7-dioxabicyclo[3.2.2]nonane through an O-neophyl-type 1,2-aryl shift: Evidence for a 1,6-dioxyl diradical intermediate

Photolysis and thermolysis of 1,5-diaryl-6,7-dioxabicyclo[3.2.2]nonane 1a-c (a: Ar=p-MeOC6H4, b: Ar=p-MeC6H4, c: Ar=Ph) were investigated. (p-Methoxyphenyl)-substituted 1a underwent a novel photo-initiated O-neophyl-type 1,2-aryl shift to afford 1-(p-methoxyphenyl)oxy-5-(p-methoxyphenyl)-8-oxabicyclo[3.2.1]octane 7a along with a small amount of 1-(p-methoxyphenyl)-3-(2-(4′-methoxyphenyl)tetrahydrofuran-2-yl) propan-1-one 4a through an 1,6-dioxyl diradical intermediate, while the thermolysis mainly afforded the 1,5-di(p-methoxyphenyl)pentan-1,5-dione 5a and 1,4-di(p-methoxyphenyl)butan-1,4-dione 8a.

Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols

Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herei

Copper(I)/DDQ-Mediated Double-Dehydrogenative Diels-Alder Reaction of Aryl Butenes with 1,4-Diketones and Indolones

A copper(I)/DDQ-mediated double-dehydrogenative Diels-Alder (DDDA) reaction of simple butenes with 1,4-diketones and indolones has been established for the first time. This strategy is based on a tandem double-dehydrogenation/Diels-Alder reaction from nonprefunctionalized starting materials, in which both a diene and dienophile were in situ generated via activation of fourfold inert C(sp3)-H bonds in one catalytic system.

Synthesis of 2,2,5-Trisubstituted 2 H-Pyrroles and 2,3,5-Trisubstituted 1 H-Pyrroles by Ligand-Controlled Site-Selective Dearomative C2-Arylation and Direct C3-Arylation

Palladium-catalyzed site-selective dearomative C2-arylation of 2,5-diaryl-1H-pyrroles with aryl chlorides was accomplished, and a series of 2,2,5-triaryl-2H-pyrroles were synthesized. In addition, the site selectivity of the reaction was switched by simply changing the ligand, and the direct C3-arylated 2,3,5-triaryl-1H-pyrroles were prepared. The obtained 2,2,5-triaryl-2H-pyrroles could be further transformed into 2,2,5,5-tetraarylpyrrolidines.

Synthesis of 1,4-Diketones via Titanium-Mediated Reductive Homocoupling of α-Haloketones

1,4-Diketones have been synthesized via a reductive homocoupling of α-haloketones. Addition of a Grignard reagent to titanium(IV) isopropoxide affords a low-valent titanium(III) intermediate that is believed to mediate a radical dimerization reaction. The

A novel coupling reaction of α-halo ketones promoted by SmI3/CuI

With SmI3 as the Lewis acid and catalyzed by CuI in DMF, α-haloketones were transformed unexpectedly into α-hydroxy-1,4-diketones in good to moderate yields. The mechanism was probed and a plausible reaction pathway was proposed. DMF was assumed to play a dual role both as a hydroxyl source and as a solvent.

Breaking bonds with electrons: Stepwise and concerted reductive cleavage of C-S, C-Se and Se-CN bonds in phenacylthiocyanates and phenacylselenocyanates

The mechanistic aspects of the electrochemical reduction of phenacylthio- and selenocyanates have been studied. With phenacylthiocyanates (1), a change in the reductive cleavage mechanism is observed as a function of the substituent on the phenyl ring. While a stepwise mechanism involving the intermediacy of a radical anion is followed for substrates bearing a strong electron withdrawing group, such as cyano and nitro substituent (1d, 1e), and a concerted mechanism is favoured for compounds bearing an electron-donating or no substituent on the phenyl ring (1a-c). A regioselective bond cleavage leads to the fragmentation of the CH2-S bond with all compounds 1a-e, further yielding the corresponding 1,4-diketone (3) as products. Contrastingly, with phenacylselenocyanates (2), two different reductive cleavages occur involving the breaking of both the CH2-Se and Se-CN bonds. Several products are obtained, all coming from nucleophilic attack at the α (phenacyl) carbon or the selenium atom.

Polymer-stabilized palladium nanoparticles for the chemoselective transfer hydrogenation of α,β-unsaturated carbonyls: Single-step bottom-Up approach

Polypyrrole stabilised palladium nanoparticles show good catalytic efficiency for the chemoselective transfer hydrogenation of α,β- unsaturated carbonyl compounds. The catalyst is very specific and selectively hydrogenates the olefins or acetylenes only,

Visible-light-induced Ci-S bond activation: Facile access to 1,4-diketones from β-ketosulfones

A novel method for the synthesis of 1,4-diketones from β-ketosulfones was developed by means of a visible light-induced Ci￡S bond activation process. Symmetrical and unsymmetrical 1,4-diketones can be easily prepared in moderate to good yields. A new and efficient method for the synthesis of 1,4-diketones from β-ketosulfones was developed by means of a visible-light-induced Ci￡S bond activation process (see scheme). Symmetrical and unsymmetrical 1,4-diketones can be easily prepared in moderate to good yields.