25856-01-3

Basic information

• Product Name: 1-(4-bromophenyl)-3-phenylpropane-1,3-dione
• Synonyms: 1-(4-bromophenyl)-3-phenylpropane-1,3-dione;1-(4-Bromophenyl)-3-phenyl-1,3-propanedione
• CAS NO: 25856-01-3
• Molecular Formula: C₁₅H₁₁BrO₂
• Molecular Weight: 303.15064
• Mol File: 25856-01-3.mol

Chemical Properties

• Melting Point: 94 °C
• Boiling Point: 443.3±30.0 °C(Predicted)
• Appearance: /
• Density: 1.422±0.06 g/cm3(Predicted)
• PKA: 8.66±0.12(Predicted)
• CAS DataBase Reference: 1-(4-bromophenyl)-3-phenylpropane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-bromophenyl)-3-phenylpropane-1,3-dione(25856-01-3)
• EPA Substance Registry System: 1-(4-bromophenyl)-3-phenylpropane-1,3-dione(25856-01-3)

Safety Data

• Hazardous Substances Data: 25856-01-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-bromophenyl)-3-phenylpropane-1,3-dione is used as an active pharmaceutical ingredient for its analgesic and sedative properties, contributing to the development of pain medications and sedatives.
Used in Pain Management:
Bromadoline is used as an analgesic agent for managing pain due to its effectiveness in reducing discomfort and alleviating pain sensations.
Used in Sedation:
As a sedative, 1-(4-bromophenyl)-3-phenylpropane-1,3-dione is used to induce a state of calmness and relaxation, which can be beneficial in various medical procedures and treatments requiring sedation.
Note: The use of bromadoline in these applications is subject to strict regulations and professional oversight due to its potential for abuse and addiction.

Upstream product

• 67-56-1 methanol 
• 64-19-7 acetic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 23565-63-1 1-(4-bromophenyl)-3-phenylpropynone 
• 932-90-1 Benzaldoxime 
• 39833-48-2 3-(4-bromophenyl)-1-phenylprop-2-yn-1-one 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 98-86-2 acetophenone 
• 586-76-5 4-Bromobenzoic acid 
• 57699-28-2 methyl 4-bromophenylglyoxalate 
• 70-11-1 α-bromoacetophenone 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 99-73-0 para-bromophenacyl bromide 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 1417818-39-3 1-(4-bromo-phenyl)-2-phenyl-ethane-1,2-diol 
• 53573-22-1 5-(p-bromophenyl)-3-phenyl-2-isoxazole 
• 53573-21-0 3-(4-bromophenyl)-5-phenylisoxazole 
• 586-76-5 4-Bromobenzoic acid 
• 57736-15-9 2-(4'-bromophenyl)-3-benzoyl-4-phenyl-1-oxa-4-azabutadiene 
• 65182-59-4 2-(4'-bromophenyl)-1,8-naphthyridine 
• 116625-83-3 (4-Bromo-phenyl)-(2-phenyl-[1,8]naphthyridin-3-yl)-methanone 
• 93944-86-6 2-bromo-1-(4-bromophenyl)-3-phenyl-1,3-propanedione 
• 61668-27-7 (+/-)-2-benzoyl-1-(4-bromo-phenyl)-4-phenyl-butane-1,4-dione 
• 61668-32-4 2-benzoyl-1-(4-bromophenyl)pentane-1,4-dione 

Relevant articles and documents

Non-metal catalytic method for preparing 1,3-diketone compounds based on acetyenic ketone

The invention discloses a non-metal catalytic method for preparing 1,3-diketone compounds based on acetyenic ketone. The preparation method is a stepwise method or a one-pot method. The stepwise method comprises the following steps: mixing an acetyenic ketone compound I, a nitrogen-containing aromatic compound II and a No.1 base for a reaction, performing separation and purification to obtain an intermediate product, mixing the intermediate product and a No.2 base for a reaction, and performing separation and purification to obtain the product; and the one-pot method comprises the following steps: firstly mixing an acetyenic ketone compound I and a nitrogen-containing aromatic compound II, adding a No.1 base, performing a reaction for a period of time, adding a No.2 base, continuing a reaction for a period of time, and finally performing separation and purification to obtain the product. The method provided by the invention has mild reaction conditions, simple operation and a higher yield, wherein the yield is generally 80% or more, and the method has greater practical application value in drug synthesis.

Analyzing the Relation between Structure and Aggregation Induced Emission (AIE) Properties of Iridium(III) Complexes through Modification of Non-Chromophoric Ancillary Ligands

Unconventionally modified dibenzoylmethane (dbm) ligands have been synthesized and successfully utilized as ancillary ligands for neutral iridium(III) complexes of the formula [Ir(dFppy)2(LX)], where dFppyH is 2-(2,4-difluorophenyl)pyridine and LX is tribenzoylmethane (tbm) or 1-phenyl-3-(4-(pyridin-2-yl)phenyl)propane-1,3-dione (pydbm). The modification of the ligands aims to prevent or enhance possible intermolecular interactions between the dFppy and/or the LX moiety in comparison with the previously reported [Ir(dFppy)2(dbm)] complex. The aggregation induced emission (AIE) properties of these complexes are significantly modulated, as a consequence of the different π–π interactions revealed by X-ray crystallography.

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.

An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources

An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.

Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones

A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.

Triphenylamine-modified difluoroboron dibenzoylmethane derivatives: Synthesis, photophysical and electrochemical properties

Two new triphenylamine functionalized difluoroboron (BF2) β-diketonate complexes, one asymmetrical 2 and the other symmetrical 3, were synthesized and fully characterized. The effects of the triphenylamine substituent on the photoluminescence,

Synthesis and photophysical properties of halogenated derivatives of (dibenzoylmethanato)boron difluoride

A series of (dibenzoylmethanato)boron difluoride (BF2DBM) derivatives with a halogen atom in one of the phenyl rings at the para-position were synthesized and used to elucidate the effects of changing the attached halogen atom on the photophysi

2-Hydroxylation of 1,3-Diketones with Atmospheric Oxygen

An efficient method for the 2-hydroxylation of 1,3-diketones by using atmospheric oxygen as an oxidant under transition-metal-free condition is described. The protocol has the advantages of using an inexpensive and stable oxidant, producing high yields, and requiring ecofriendly conditions.

Transition-metal-free formal decarboxylative coupling of ?±-oxocarboxylates with ?±-bromoketones under neutral conditions: A simple access to 1,3-diketones

A transition-metal-free formal decarboxylative coupling reaction between ?±-oxocarboxylates and ?±-bromoketones to synthesize 1,3-diketone derivatives is presented. In this reaction, a broad scope of substrates can be employed, and neither a metal-based reagent nor an additional base is required. DFT calculations reveal that this reaction proceeds through a coupling followed by decarboxylation mechanism and the ?±-bromoketone unprecedentedly serves as a nucleophile under neutral conditions. The rate-determining step is an unusual hydrogen-bond-assisted enolate formation by thermolysis.

Asymmetric transfer hydrogenation of unsymmetrical benzils

In this paper, the asymmetric transfer hydrogenation of unsymmetrical benzils with m, p-substituents was conducted with a substrate/catalyst molar ratio of 100 at 40°C for 24 h to produce (S,S)-hydrobenzoins in good yields (76.2% to 97.1%) with high diastereomeric (syn/anti = 10.8 to 29.7/1) and enantiomeric purities (86.1%ee syn to 98.9%ee syn). Unfortunately, the unsymmetrical benzils with the o-substituents such as electron-donating (R = CH3, OCH3) and electron-withdrawing groups (R = F, Cl, CF3) resulted in poor yields (0% to 31.2%), even at 40°C for 72 h. These products had inefficient diastereoselectivities (syn/anti = 1.5 to 5.0/1) caused by steric effects. Furthermore, the results of a dynamic-kinetic study were used to propose a plausible reaction pathway of unsymmetrical benzil using 3-methoxy-1,2-diphenyl ethanedione as an example.