3457-48-5

Basic information

• Product Name: 4,4'-DIMETHYLBENZIL
• Synonyms: 1,2-Bis(4-methylphenyl)-1,2-ethanedione;1,2-Di-p-tolyl-ethane-1,2-dione;di-p-tolylethanedione;Ethanedione, bis(4-methylphenyl)-;Ethanedione,bis(4-methylphenyl)-;LABOTEST-BB LT00159323;4,4'-DIMETHYLDIBENZOYL;4,4'-DIMETHYLBENZIL
• CAS NO: 3457-48-5
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.28
• EINECS: 222-388-2
• Product Categories: Aromatic Ketones (substituted);Benzil and Benzoin Compounds;Organic Photoinitiators;Polymerization Initiators
• Mol File: 3457-48-5.mol

Chemical Properties

• Melting Point: 102-104 °C(lit.)
• Boiling Point: 211 °C (7 mmHg)
• Flash Point: 168.6 °C
• Appearance: yellow crystals or needles
• Density: 1.119±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.6290 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 4,4'-DIMETHYLBENZIL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-DIMETHYLBENZIL(3457-48-5)
• EPA Substance Registry System: 4,4'-DIMETHYLBENZIL(3457-48-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26
• WGK Germany: 3
• Hazardous Substances Data: 3457-48-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 1296, 1973 DOI: 10.1021/ja00785a047Tetrahedron Letters, 34, p. 3897, 1993 DOI: 10.1016/S0040-4039(00)79257-4

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 99-94-5 p-Toluic acid 
• 79-37-8 oxalyl dichloride 
• 108-88-3 toluene 
• 460-19-5 ethanedinitrile 
• 2789-88-0 1,2-bis(4-methylphenyl)acetylene 
• 1218-89-9 4,4'-dimethylbenzoin 
• 4342-61-4 1,2-dichlorotetramethylsilane 
• 874-60-2 4-methyl-benzoyl chloride 
• 2417-95-0 p-tolyllithium 
• 106675-70-1 N¹,N²-dimethoxy-N¹,N²-dimethyloxalamide 
• 71193-32-3 2-chloro-1,2-bis(4-methylphenyl)ethanone 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 38424-23-6 (E)-4,4'-dimethylstilbene 

Downstream Products

• 2216-49-1 triphenylmethyl radical 
• 1218-89-9 4,4'-dimethylbenzoin 
• 92405-78-2 5,6-bis(p-methylphenyl)-2,3-dihydropyrazine 
• 62497-27-2 3,4-bis(4-methylphenyl)thiophene-2,5-dicarboxylic acid 
• 40030-85-1 bis-(4,4'-dimethyl-α'-oxo-bibenzyl-α-ylidene)-hydrazine 
• 858007-60-0 4,4'-dimethyl-benzil-dihydrazone 
• 2695-79-6 bis-p-tolylhydroxyacetic acid 
• 5173-28-4 (1R,2S)-1,2-Di-p-tolyl-ethane-1,2-diol 
• 5314-79-4 α,α'-bis-benzoyloxy-4,4'-dimethyl-stilbene 
• 16112-18-8 2,4,5-tri(4-methylphenyl)-1,3-oxazole 
• 99-94-5 p-Toluic acid 
• 22985-87-1 meso-2,3-bis(4-methylphenyl)-2,3-butanediol 
• 22985-88-2 dl-2,3-bis(4-methylphenyl)-2,3-butanediol 
• 40030-78-2 4,4'-dimethylbenzil monohydrazone 

Relevant articles and documents

Electrochemical oxidation-induced benzyl C–H carbonylation for the synthesis of aromatic α-diketones

Electrochemical oxidation-induced direct carbonylation of benzyl C–H bond for the synthesis of aromatic α-diketones is described. In this process, tetrabutylammonium iodide (nBu4NI) not only acts as an electrolyte, but its iodine anion is oxidized to an iodine radical at the anode, acting as a hydrogen atom transfer agent. The iodine radical extracts the benzyl hydrogen atom and causes the carbonylation of the benzyl position, where O2 in the air is used as an oxygen source.

One-pot synthesis, structural analysis, and oxidation applications of a series of diaryltellurium dicarboxylates

This paper presents a concise and efficient one-pot synthesis of a variety of functionalized diaryltellurium dicarboxylates. The method is based on a mild photosensitized oxygenation of cheap and readily available carboxylic acids. The molecular structures of the diaryltellurium dicarboxylates were determined unambiguously using single-crystal X-ray diffraction analysis. The thus obtained diaryltellurium dicarboxylates were used to study the oxidation of benzoin derivatives.

Synthesis of 1,2-diketones by mercury-catalyzed alkyne oxidation

The first mercury-catalyzed synthesis of 1,2-diketones by alkyne oxidation has been developed. This inexpensive method extends the potential of mercury catalysis and allows the rapid construction of various 1,2-diketones and α-carbonyl amides in good yields with high functional group tolerance.

Catalyst-Free and Transition-Metal-Free Approach to 1,2-Diketones via Aerobic Alkyne Oxidation

A catalyst-free and transition-metal-free method for the synthesis of 1,2-diketones from aerobic alkyne oxidation was reported. The oxidation of various internal alkynes, especially more challenging aryl-alkyl acetylenes, proceeded smoothly with inexpensive, easily handled, and commercially available potassium persulfate and an ambient air balloon, achieving the corresponding 1,2-diketones with up to 85% yields. Meanwhile, mechanistic studies indicated a radical process, and the two oxygen atoms in the 1,2-diketons were most likely from persulfate salts and molecular oxygen, respectively, rather than water.

Visible-Light-Induced Photocatalytic Oxidative Decarboxylation of Cinnamic Acids to 1,2-Diketones

A concerted metallophotoredox catalysis has been realized for the efficient decarboxylative functionalization of α,β-unsaturated carboxylic acids with aryl iodides in the presence of perylene bisimide dye to afford 1,2-diketones.

One-pot cascade synthesis of α-diketones from aldehydes and ketones in water by using a bifunctional iron nanocomposite catalyst

A new methodology for the synthesis of α-diketones was reportedviaa one-pot cascade process from aldehydes and ketones catalyzed by a bifunctional iron nanocomposite using H2O2as a green oxidant in water. The one-pot strategy showed excellent catalytic stability, comprehensive suitability of substrates and important practical utility for directly synthesizing biologically active and medicinally valuable N-heterocyclesviaan intermittent process.

1-butyl-3-methylimidazol-2-ylidene as an efficient catalyst for cross-coupling between aromatic aldehydes and N-aroylbenzotriazoles

Cross-coupling of aromatic aldehydes with N-aroylbenzotriazoles in [Bmim]Br in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) provided an efficient procedure for the synthesis of 1,2-diarylethane-1,2-diones.

Synthesis of unsymmetrical benzilsviapalladium-catalysed a-arylation-oxidation of 2-hydroxyacetophenones with aryl bromides

A diverse set of unsymmetrically substituted benzils were facilely synthesised by a cross-coupling reaction between 2-hydroxyacetophenones and aryl bromides in the presence of a palladium catalyst. Experimental studies suggested a reaction mechanism involving a one-pot tandem palladium-catalysed a-arylation and oxidation, where aryl bromides play a dual role as mild oxidants as well as arylating agents.

Dimethyl Sulfoxide as an Oxygen Atom Source Enabled Tandem Conversion of 2-Alkynyl Carbonyls to 1,2-Dicarbonyls

A tandem transformation of 2-alkynyl carbonyl compounds by means of a CuBr2/I2/DMSO/water system is developed, enabling the fromation of various functionalized 1,2-dicarbonyl compounds, including 1,2-diketones, α-keto amides and α-keto ester. This Cu-promoted iodine-mediated tandem procedure employs DMSO as the oxygen atom source of the formed carbonyl group through iodonium ion formation, nucleophilic DMSO addition and C?C bond cleavage cascades. (Figure presented.).

Copper/Iodine-Cocatalyzed C-C Cleavage of 1,3-Dicarbonyl Compounds Toward 1,2-Dicarbonyl Compounds

A new, general oxidative route to transformations of 1,3-dicarbonyl compounds to 1,2-dicarbonyl compounds by merging copper and I2 catalysis is described. This method is applicable to broad 1,3-dicarbonyl compounds, including 1,3-diketones, 1,3-keto esters and 1,3-keto amides. Mechanistical studies show that the reaction is achieved via the C–C bond cleavage and CO release cascades.