41169-42-0

Basic information

• Product Name: 2,2-dimethyl-1,3-diphenylpropane-1,3-dione
• Synonyms: 1,3-Propanedione, 2,2-dimethyl-1,3-diphenyl-
• CAS NO: 41169-42-0
• Molecular Formula: C₁₇H₁₆O₂
• Molecular Weight: 252.3077
• Mol File: 41169-42-0.mol

Chemical Properties

• Boiling Point: 402.7°C at 760 mmHg
• Flash Point: 150.8°C
• Density: 1.097g/cm³
• Vapor Pressure: 1.07E-06mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: 2,2-dimethyl-1,3-diphenylpropane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-dimethyl-1,3-diphenylpropane-1,3-dione(41169-42-0)
• EPA Substance Registry System: 2,2-dimethyl-1,3-diphenylpropane-1,3-dione(41169-42-0)

Safety Data

• Hazardous Substances Data: 41169-42-0(Hazardous Substances Data)

Usage

Uses

Used in Polymer Production:
Benzil is utilized as a photo-initiator in the polymerization of monomers, which is crucial for the manufacturing process of plastics and adhesives. Its role in this application is to facilitate the transformation of monomers into polymers under the influence of light, thereby enhancing the efficiency and speed of the polymerization process.
Used in Pharmaceutical Synthesis:
Benzil serves as an important intermediate in the synthesis of various pharmaceuticals. Its chemical properties make it a valuable component in the creation of new drug molecules, contributing to the development of novel treatments and therapies.
Used in Dye Synthesis:
In the dye industry, benzil is employed in the synthesis of different types of dyes. Its chemical structure allows for the production of dyes with specific color characteristics, which are essential for various applications such as textiles, printing, and other industrial uses.
Used in Organic Chemistry Research:
Due to its ability to undergo a variety of chemical reactions, benzil is also a popular compound in organic chemistry research. It is used in academic and industrial laboratories to study reaction mechanisms, test new synthetic methods, and explore the boundaries of organic chemistry.

Upstream product

• 7321-55-3 2,2-dimethylmalononitrile 
• 5659-93-8 2,2-Dimethylmalonyl chloride 
• 71-43-2 benzene 
• 120-46-7 1,3-diphenylpropanedione 
• 74-88-4 methyl iodide 
• 13118-38-2 1-benzylidene-2-(diphenylmethylidene)hydrazine 
• 75990-52-2 3-hydroxy-2,2-dimethyl-1,3-diphenylpropan-1-one 
• 546-67-8 lead(IV) tetraacetate 
• 99390-63-3 2,2-dimethyl-1,3-diphenyl-1,3-propanedione dioxime 
• 72229-10-8 cis-3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole 
• 10409-54-8 2-bromo-2-methyl-1-phenyl-propan-1-one 
• 98-88-4 benzoyl chloride 
• 30169-45-0 4,4-dimethyl-3,5-diphenyl-4H-pyrazole 
• 137363-40-7 3-hydroxy-4,4-dimethyl-3,5,5-triphenyl-1,2-dioxolane 

Downstream Products

• 151221-89-5 3-hydroxy-2,2-dimethyl-1,3-diphenyl-butan-1-one 
• 76-84-6 triphenylmethyl alcohol 
• 611-70-1 phenyl isopropyl ketone 
• 51942-52-0 4,4-dimethyl-3,5-diphenyl-4,5-dihydroisoxazol-5-ol 
• 93-89-0 benzoic acid ethyl ester 
• 113768-17-5 2,2-dimethyl-1,3-diphenylpropane-1,3-dione dioxime 
• 95581-19-4 meso-1,3-Diphenyl-2,2-dimethyl-1,3-propandiol 
• 95581-18-3 (+/-)-1,3-diphenyl-2,2-dimethyl-1,3-propanediol 
• 30169-45-0 4,4-dimethyl-3,5-diphenyl-4H-pyrazole 
• 50555-61-8 3,3-dimethyl-1,2-diphenyl-1-cyclopropene 
• 41169-43-1 cis-3,3-dimethyl-1,2-diphenylcyclopropane-1,2-diol 
• 123-72-8 butyraldehyde 
• 98-86-2 acetophenone 
• 65-85-0 benzoic acid 

Relevant articles and documents

Influence of phase transfer catalyst structure on the E : Z ratio in the O-alkylation of an enolate

Both C- vs. O-alkylations and Z vs. E enol ether formation from 2-methyl-1,3-diphenylpropane-1,3-dione (1) can be influenced by the structure of the phase transfer catalyst. O-Methylation is the major process in the PTC reaction of 1 with dimethyl sulfate

Structural insights into the desymmetrization of bulky 1,2-dicarbonyls through enzymatic monoreduction

Benzil reductases are dehydrogenases preferentially active on aromatic 1,2-diketones, but the reasons for this peculiar substrate recognition have not yet been clarified. The benzil reductase (KRED1-Pglu) from the non-conventional yeast Pichia glucozyma showed excellent activity and stereoselectivity in the monoreduction of space-demanding aromatic 1,2-dicarbonyls, making this enzyme attractive as biocatalyst in organic chemistry. Structural insights into the stereoselective monoreduction of 1,2-diketones catalyzed by KRED1-Pglu were investigated starting from its 1.77 ? resolution crystal structure, followed by QM and classical calculations; this study allowed for the identification and characterization of the KRED1-Pglu reactive site. Once identified the recognition elements involved in the stereoselective desymmetrization of bulky 1,2-dicarbonyls mediated by KRED1-Pglu, a mechanism was proposed together with an in silico prediction of substrates reactivity.

Versatile CuI/Pd0 dual catalysis for the synthesis of quaternary α-allylated carbonyl compounds: Development, mechanistic investigations and scope

We report herein a versatile cooperative dual catalysis reaction based on a CuI/Pd0 system. Mechanistic investigation shows that every component plays a crucial role in determining the reaction outcome. The reaction is successfully extended to various substrates; such as α,β-unsaturated ketones, malonates and coumarins. The strategy tolerates different substitution patterns and affords good yields for each family of substrates.

Clemmensen reduction. XII The synthesis and acidolysis of some diaryl-substituted cyclopropane-1,2-diols. The possible involvement of a cyclopropyl cation

The generation of a number of 1,2-diarylcyclopropane-1,2-diols is reported. Reaction of these in situ with acid gives, primarily, an α,β-unsaturated ketone in which the aryl substituent attached to the double bond is that which is best able to stabilize a benzylic cation. It is proposed that the reaction proceeds by O-protonation of the cyclopropane- 1,2-diol, followed by loss of water and opening of the resulting cyclopropyl cation and final deprotonation. Such initial O-protonation contrasts with the C-protonation normally observed in the acidolysis of cyclopropanols and other dialkyl- and alkylaryl-cyclopropane-1,2-diols.

Additivity of the Electronic Meta-Substituent Effect in 3,5-Disubstituted Cumyl Radicals Assessed by the EPR D Parameter of 1,3-Arylcyclopentane-1,3-diyl Triplet Diradicals

The D parameter (EPR zero-field splitting) of the 3,3′,5,5′-tetrasubstituted triplet diradicals 6 (X = X′ = H, NO2, CH3, OAc, OCH3, NH2, and OH) were determined in a MTHF matrix at 77 K and serves as a spectrosc

Photochemistry of nonconjugated diketones: internal self-quenching and energy transfer

The triplet state behavior of nine α,ο-dibenzoylalkanes indicates the occurrence of a rapid quenching interaction between the two carbonyl groups.This quenching is fastest (k=3E7 s-1) in dibenzoylbutane, is slightly slower (ca.E7 s-1) in dibenzoylethane, dibenzoylpentane, and 2,2-dibenzoylpropane, but is absent in 1,3-dibenzoylpropane.It also occurs in several "mixed" 1,4-diaroylbutanes incorporating p-ethylbenzoyl or p-methoxybenzoyl chromophores.This internal self-quenching is interpreted as the intramolecular counterpart of the well-know bimolecular self-quenching of aryl ketones, although no exact mechanism can be proposed.Such internal quenching does not occur as rapidly, if at all, in three "turned around" diketones: δ-(p-acetylphenyl)valerophenone, δ-(p-acetylphenoxy)valerophenone, and γ-(p-acetylphenoxy)butyrophenone.This fact, together with the varying rates of internal self-quenching in the dibenzoylalkanes, indicates the necessity for a very specific and close orientation of the two carbonyl groups for self-quenching.In the mixed diketones containing a p-alkylbenzoyl group, triplet excitation appears to be fully equilibrated between the two chromophores.However, in those containing a p-methoxybenzoyl group, excitation does not fully equilibrate before triplet decay, as evidenced by different quenching efficiencies for products from the two carbonyls.Analysis indicates intramolecular energy transfer rate constants -1.These are sufficiently lower than in other bichromophoric systems to suggest relatively slow energy hopping in the polymers of phenyl vinyl ketone.Key words: nonconjugated diketones, dibenzoylalkanes, sefl-quenching, energy transfer, triplet ketones.

Diastereo- and regioselective synthesis of diquinanes and related systems from tricyclo[3.3.0.02,4]octanes by chemical electron transfer (CET)

A new synthetic methodology for diquinanes by one-electron oxidation of tricyclo[3.3.0.02,4]octanes and subsequent stereocontrolled rearrangement is provided. The latter compounds are conveniently accessible through acid-catalyzed isopyrazole cycloaddition, followed by hydrogenation and photoextrusion of molecular nitrogen. The oxidative rearrangement of the tricyclooctanes proceeds catalytically and cleanly to afford regio- and diastereoselectively the corresponding diquinanes.

Synthesis and Thermolysis of Ketal Derivatives of 3-Hydroxy-1,2-dioxolanes

3--3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (2), 3-methoxy-3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (3), and 3-acetoxy-3,4,4,5-tetramethyl-5-phenyl-1,2-dioxolane (4) were synthesized from the corresponding 3-hydroxy-1,2-dioxolane (1a) under basic conditions. 3-Acetoxy-4,4-dimethyl-3,5,5-triphenyl-1,2-dioxolane (5) was also synthesized via this approach.Under acidic conditions, 3-hydroxy-1,2-dioxolane 1a underwent quantitative decomposition to phenol and 3,3-dimethyl-2,4-pentanedione.This competing degradation was dependent on the nature of the substituents at position-5.Methyl groups at position-5 slowed the degradative rearrangement whereas phenyl groups favored it. 3-Methoxy- and 3-(allyloxy)-4,4,5,5-tetramethyl-3-phenyl-1,2-dioxolanes (6, 7) were synthesized under acidic conditions from the appropriate 1,2-dioxolane precursors and the corresponding alcohols.At 60 deg C, derivatized 1,2-dioxolanes 2-7 were found to be more stable than the corresponding 3-hydroxy-1,2-dioxolanes.The first order rate constants for the thermolysis of 1,2-dioxolanes 2-7 were determined.Product studies showed that thermolysis of 2-5 yielded pairs of ketones and derivatized carboxylic acids.In addition to R-group migration products, an acetoxy migration product was observed for the thermolysis of 4.Thermolysis of 6 at 60 deg C in benzene yielded methyl benzoate and pinacolone, quantitatively.Thermolysis of 7 yielded products analogous to those for 6.No evidence for internal trapping of radicals by the carbon-carbon double bond of the allyloxy group in 7 was found.The thermolysis appeared to proceed with peroxy bond homolysis as the rate-determining step.Subsequent β-scissions of the intermediate 1,5-oxygen diradical with interesting rearrangements that show a high preference for alkyl vs phenyl migration account for the observed product distributions.The results suggest that the β-scission/rearrangement mechanism may not be concerted but rather stepwise to yield 1,3-diradical and carbonyl fragments.

Electronic Substituent Effects on the Acid-Catalyzed + + 2> Cycloaddition of Isopyrazoles with Cyclopentadiene and the Photochemical and Thermal Denitrogenation of the Resulting 1,4-Diaryl-7,7-dimethyl-2,3-diazabicyclohept-2-ene Azoalk

Eight symmetrically disubstituted 3,5-diaryl-4,4-dimethylisopyrazoles 6 with para and meta substituents (OMe, Me, H, F, Cl, Br, CN, NO2) and two unsymmetrically para-substituted derivatives (OMe and NO2; Me and CO2Me) were synthesized from the correspondi

Photochemical Reaction of 3-Hydroxy-1-(o-methylaryl)alkan-1-ones: Formation of Cyclopropane-1,2-diols and Benzocyclobutenols through β- and γ-Hydrogen Abstractions

Irradiation of 3-hydroxy-2,2-dimethyl-1-(o-methylaryl)-alkan-1-ones 1a-h having a bulky alkyl group or an aryl group on C-3 in methanol gave trans- and cis-cyclopropane-1,2-diols 2a-g and 3a, c-f, h and benzocyclobutenols 4a-h through β- and γ-hydrogen abstractions.Irradiation of 3-hydroxy-2,2-dimethyl-1-(o-methylphenyl)-alkan-1-ones 1i-k having ethyl, methyl or no substituent at C-3 gave benzocyclobutenols 4i-k and 1,3-diketones 5i, j, but no cyclopropane-1,2-diols.The cyclopropane-1,2-diols were sensitive to air and readily oxidized to the corresponding 1,3-diketones.Irradiation of 3-hydroxy-4,4-dimethyl-1-(o-methylaryl)pentan-1-ones 8a, b having a methyl group or no substituent on C-2 gave benzocyclobutenols 9a, b, the peroxide 10 and phthalides 11a, b. 3-Hydroxy-2,2-dimethyl-1,3-diphenylpropan-1-one 12a and 3-hydroxy-2,2,4-trimethylpentan-1-one 12b also underwent photocyclization through β-hydrogen abstraction to give cyclopropane-1,2-diols 13a, b and 14.