1469-94-9

Basic information

• Product Name: 1-(2-HYDROXYPHENYL)-3-PHENYL-1,3-PROPANEDIONE
• Synonyms: 2-(3-Oxo-3-phenylpropanoyl)phenol;1-(O-HYDROXYPHENYL)-3-PHENYL-1,3-PROPANEDIONE;1-(2-HYDROXYPHENYL)-3-PHENYL-1,3-PROPANEDIONE;1-(2-HYDROXYLPHENYL)-3-PHENYL-1,3-PROPANEDIONE;1-(2-HYDROXYPHENYL)-3-PHENYLPROPANE-1,3-DIONE;O-HYDROXYDIBENZOYLMETHANE;TIMTEC-BB SBB008009;1-(2-hydroxyphenyl)-3-phenyl-3-propanedione
• CAS NO: 1469-94-9
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25
• Product Categories: C15 to C38;Carbonyl Compounds;Ketones
• Mol File: 1469-94-9.mol

Chemical Properties

• Melting Point: 120-122 °C(lit.)
• Boiling Point: 421 °C at 760 mmHg
• Flash Point: 222.6 °C
• Appearance: yellow crystalline powder
• Density: 1.23 g/cm³
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Refractive Index: 1.61
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.80±0.30(Predicted)
• CAS DataBase Reference: 1-(2-HYDROXYPHENYL)-3-PHENYL-1,3-PROPANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-HYDROXYPHENYL)-3-PHENYL-1,3-PROPANEDIONE(1469-94-9)
• EPA Substance Registry System: 1-(2-HYDROXYPHENYL)-3-PHENYL-1,3-PROPANEDIONE(1469-94-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1469-94-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Hydroxyphenyl)-3-phenyl-1,3-propanonedione is used as an intermediate compound for the synthesis of various pharmaceuticals, including drugs with potential therapeutic applications. Its unique chemical structure allows for the development of new drugs with improved efficacy and reduced side effects.
Used in Chemical Research:
As a chalcone, 1-(2-Hydroxyphenyl)-3-phenyl-1,3-propanonedione is used as a research compound in the field of organic chemistry. It serves as a model for studying the properties and reactions of chalcone derivatives, which can lead to the discovery of new chemical reactions and the development of novel compounds with potential applications in various industries.
Used in Material Science:
The unique chemical and physical properties of 1-(2-Hydroxyphenyl)-3-phenyl-1,3-propanonedione make it a candidate for use in the development of new materials with specific properties. It can be used in the synthesis of advanced materials for various applications, such as electronics, optics, and sensors.
Used in Cosmetics Industry:
Due to its natural origin and unique chemical properties, 1-(2-Hydroxyphenyl)-3-phenyl-1,3-propanonedione can be used as an active ingredient in the cosmetics industry. It may have potential applications in the development of skincare products, hair care products, and other personal care items, offering benefits such as antioxidant, anti-inflammatory, or UV protection properties.

Synthesis Reference(s)

Synthesis, p. 839, 1992 DOI: 10.1055/s-1992-26241

InChI:InChI=1/C15H12O3/c16-13-9-5-4-8-12(13)15(18)10-14(17)11-6-2-1-3-7-11/h1-9,16H,10H2

Upstream product

• 525-82-6 FLAVONE 
• 64-17-5 ethanol 
• 4010-33-7 2-acetylphenyl benzoate 
• 3999-70-0 potassium n-butoxide 
• 93-89-0 benzoic acid ethyl ester 
• 118-93-4 o-hydroxyacetophenone 
• 98-88-4 benzoyl chloride 
• 80282-49-1 1-(1-(2-hydroxyphenyl)-2-methanone)-1H-imidazole 
• 136003-86-6 1-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-phenyl-propane-1,3-dione 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 122-79-2 Phenyl acetate 
• 614-20-0 3-oxo-3-phenylpropionic acid 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 70460-60-5 2-phenyl-chroman-3,4-dione 
• 121507-65-1 2,2,4-Triphenyl-2H-benzopyran 
• 525-82-6 FLAVONE 
• 67139-38-2 3-Phenyl-5-(2-hydroxyphenyl)isoxazole 
• 5067-18-5 (3-hydroxybenzofuran-2-yl)(phenyl)methanone 
• 19726-10-4 2-(1-phenyl-5-phenyl-1H-pyrazol-3-yl)phenol 
• 30455-85-7 5-amino-2-phenyl-3H-chromeno[4,3,2-de][1,6]naphthyridine-4-carbonitrile 
• 130824-67-8 (Z)-1-(2-Hydroxy-phenyl)-3-methoxy-3-phenyl-propenone 
• 130824-69-0 (E)-2,7-Dimethoxychalcone 
• 130824-65-6 (Z)-2,7-Dimethoxychalcone 
• 116750-07-3 Furan-2-carboxylic acid 2-(3-oxo-3-phenyl-propionyl)-phenyl ester 
• 116625-84-4 (2-Hydroxy-phenyl)-(2-phenyl-[1,8]naphthyridin-3-yl)-methanone 
• 65182-56-1 2-(2-hydroxyphenyl)-1,8-naphthyridine 
• 93-58-3 benzoic acid methyl ester 

Relevant articles and documents

Synthesis, photophysical and electrochemical properties of novel and highly fluorescent difluoroboron flavanone β-diketonate complexes

Difluoroboron β-diketonates complexes are highly luminescent with extensive properties such as their fluorescence both in solution and in solid state and their high molar extinction coefficients. Due to their rich optical properties, these compounds have been studied for their applications in organic electronics such as in self-assembly and applications in biosensors, bio-imaging and optoelectronic devices. The easy and fast synthesis of difluoroboron β-diketonate (BF2dbm) complexes makes their applications even more attractive. Although many different types of difluoroboron β-diketonates complexes have been studied, the cyclic flavanone analogues of these compounds have never been reported in the literature. Therefore, the present work aims to synthesize difluouroboron flavanone β-diketonate complexes, study their photophysical and electrochemical properties and assess their suitability for applications in optoelectronic devices. The synthesis was based on a Baker-Venkataraman reaction which initially provided substituted diketones, which were subsequently reacted with aldehydes to afford the proposed flavanones. The complexation was achieved by reacting flavanones and BF3·Et2O and in total 9 novel compounds were obtained. A representative difluoroboron flavanone complex was subjected to single crystal X-ray diffraction to unequivocally confirm the chemical structure. A stability study indicated only partial degradation of these compounds over a few days in a protic solvent at elevated temperatures. Photophysical studies revealed that the substituent groups and the solvent media significantly influence the electrochemical and photophysical properties of the final compounds, especially the molar absorption coefficient, fluorescence quantum yields, and the band gap. Moreover, the compounds exhibited a single excited-state lifetime in all studied solvents. Computational studies were employed to evaluate ground and excited state properties and carry out DFT and TDDFT level analysis. These studies clarify the role of each state in the experimental absorption spectra as well as the effect of the solvent.

Synthesis of 2,2′-biflavanones from flavone via electrolytic reductive coupling

Flavone (1) was easily reduced by using the electrochemical method to give two hydrodimers of 2,2′-biflavanone(racemate) (5a) and 2,2′-biflavanone(meso) (5b) and one reductive product of flavanone (6). Their yields were dependent on the nature of electrodes, the kinds of supporting electrolytes and the reaction temperature. They were found to afford higher yields of 2,2′-biflavanone(racemate) (5a) and 2,2′-biflavanone (meso) (5b) (32.4% and 24.8%, 35.8% and 13.4%, respectively,) in the reaction conditions of Pb(-)/C(+)-H2SO4-TF/mol and C(-)/C(+)-H 2SO4-5F/mol.

Catalytic and stoichiometric flavanone oxidation mediated by nonheme oxoiron(iv) complexes as flavone synthase mimics: Kinetic, mechanistic and computational studies

The present study describes the first example of the stoichiometric and catalytic oxidation of flavanone by synthetic nonheme oxoiron(iv) complexes and their precursor iron(ii) complexes with m-CPBA as the terminal oxidant. These models, including detailed kinetic, mechanistic and computational studies, may serve as the biomimics of flavone synthase (FS) enzymes.

Synthesis, structure and acetylcholinesterase inhibition activity of new diarylpyrazoles

A variety of diarylpyrazole derivatives III-VI were synthesized and structurally characterized using FTIR, 1H and 13C NMR spectroscopy, and in case of compound VIb by X-ray single crystal analysis. The in vitro biological studies rev

In vitro photoprotective evaluation and development of novel nanoemulsion with chromone derivative

Chromone derivatives exhibiting high absorbance values in the UVA/UVB region were synthesized, and their photoprotective properties were evaluated. Chromones were prepared according to known literature procedures and characterized by high resolution mass

Comparison of nonheme manganese‐ and iron‐containing flavone synthase mimics

Heme and nonheme‐type flavone synthase enzymes, FS I and FS II are responsible for the synthesis of flavones, which play an important role in various biological processes, and have a wide range of biomedicinal properties including antitumor, antimalarial, and antioxidant activities. To get more insight into the mechanism of this curious enzyme reaction, nonheme structural and functional models were carried out by the use of mononuclear iron, [FeII(CDA‐BPA*)]2+ (6) [CDA‐BPA = N,N,N’,N’‐tetrakis‐(2‐pyridylmethyl)‐cyclohexanediamine], [FeII(CDA‐BQA*)]2+ (5) [CDA‐BQA = N,N,N’,N’‐tetrakis‐(2‐quinolilmethyl)‐cyclohexanediamine], [FeII(Bn‐TPEN)(CH3CN)]2+ (3) [Bn‐ TPEN = N‐benzyl‐N,N’,N’‐tris(2‐pyridylmethyl)‐1,2‐ diaminoethane], [FeIV(O)(Bn‐TPEN)]2+ (9), and manganese, [MnII(N4Py*)(CH3CN)]2+ (2) [N4Py* = N,N‐bis(2‐pyridylmethyl)‐1,2‐di(2‐pyridyl)ethyl-amine)], [MnII(Bn‐TPEN)(CH3CN)]2+ (4) complexes as catalysts, where the possible reactive inter-mediates, high‐valent FeIV(O) and MnIV(O) are known and well characterised. The results of the catalytic and stoichiometric reactions showed that the ligand framework and the nature of the metal cofactor significantly influenced the reactivity of the catalyst and its intermediate. Comparing the reactions of [FeIV(O)(Bn‐TPEN)]2+ (9) and [MnIV(O)(Bn‐TPEN)]2+ (10) towards flavanone under the same conditions, a 3.5‐fold difference in reaction rate was observed in favor of iron, and this value is three orders of magnitude higher than was observed for the previously published [FeIV(O)(N2Py2Q*)]2+ [N,N‐bis(2‐quinolylmethyl)‐1,2‐di(2‐pyridyl)ethylamine] species.

Trypanocidal activity of flavanone derivatives

Chagas disease, also known as American trypanosomiasis, is classified as a neglected disease by the World Health Organization. For clinical treatment, only two drugs have been on the market, Benznidazole and Nifurtimox, both of which are recommended for use in the acute phase but present low cure rates in the chronic phase. Furthermore, strong side effects may result in discontinuation of this treatment. Faced with this situation, we report the synthesis and trypanocidal activity of 3-benzoyl-flavanones. Novel 3-benzoyl-flavanone derivatives were prepared in satisfactory yields in the 3-step synthetic procedure. According to recommended guidelines, the whole cell-based screening methodology was utilized that allowed for the simultaneous use of both parasite forms responsible for human infection. The majority of the tested compounds displayed promising anti-Trypanosoma cruzi activity and the most potent flavanone bearing a nitrofuran moiety was more potent than the reference drug, Benznidazole.

Novel Bifunctionalization of Activated Methylene: Base-Promoted Trifluoromethylthiolation of β-Diketones with Trifluoromethanesulfinyl Chloride

A novel bifunctionalization of activated methylene was achieved successfully through the base-promoted trifluoromethylthiolation of β-diketones or β-ketoesters with trifluoromethanesulfinyl chloride. A series of α-trifluoromethylthiolated α-chloro-β-diketones and α-chloro-β-ketoesters were obtained in moderate to good yields under mild conditions. When β-diketones containing a phenyl group with a hydroxyl or amino substituent at the ortho position were used as substrates, intramolecular trifluoromethylthiolation/cyclization reaction took place to give the corresponding cyclic products. Furthermore, the protocol could be extended to perfluoroalkylthiolation with the sodium perfluoroalkanesulfinate/POCl3 system. On the basis of experimental results, plausible mechanisms are proposed.

Method for synthesizing 2-aryl benzopyrone flavonoid derivatives

The invention relates to a method for synthesizing 2-aryl benzopyrone flavonoid derivatives, and relates to a method for synthesizing a compound, the method for synthesizing 2-aryl benzopyrone flavonoid derivatives is suitable for the synthesis of 2-aryl benzopyrone flavonoid derivatives containing different substituents. The method aims to solve the technical problems of low yield, long reactionperiod, and complicated post-treatment and high operation difficulty of the existing synthesis method of the ketone flavonoid derivative. The method comprises the following steps of: 1, preparing beta-propanedione compounds; 2, preparing flavonoid compound 2-aryl benzopyranones. The method completes esterification and rearrangement in one step, which is simple and practical, reduces intermediate links of reaction, saves separation and purification of intermediate products, improves utilization rate of raw materials, reduces reaction temperature, shortens reaction time under microwave radiation, reduces solvent consumption, the post-treatment is relatively simple, the yield is relatively high and no by-products exist, and can also react in the presence of a small amount of water, the reaction is easy to operate, and the method is suitable for industrial production. The method belongs to the technical field of compound synthesis.

Rh(III)-Catalyzed Aldehydic C?H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides

A novel aldehydic C?H functionalization reaction between salicylaldehydes and sulfoxonium ylides has been developed under rhodium(III) catalysis, affording coupling products in moderate to good yields. A plausible mechanism involving aldehydic C(sp2)?H activation by rhodium(III) and rhodium(III) catalyzed carbene insertion is also proposed. It was also found that the aldehydic C?H functionalization followed by dehydrative cyclization was able to produce flavonoids in one-pot. (Figure presented.).