581-83-9

Basic information

• Product Name: 1-(4-BIPHENYLYL)-4,4,4-TRIFLUORO-1,3-BUTANEDIONE
• Synonyms: 1-(4-BIPHENYLYL)-4,4,4-TRIFLUORO-1,3-BUTANEDIONE
• CAS NO: 581-83-9
• Molecular Formula: C₁₆H₁₁F₃O₂
• Molecular Weight: 292.255
• Mol File: 581-83-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 372.9°Cat760mmHg
• Flash Point: 134.3°C
• Appearance: /
• Density: 1.255g/cm³
• Vapor Pressure: 9.3E-06mmHg at 25°C
• Refractive Index: 1.518
• CAS DataBase Reference: 1-(4-BIPHENYLYL)-4,4,4-TRIFLUORO-1,3-BUTANEDIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-BIPHENYLYL)-4,4,4-TRIFLUORO-1,3-BUTANEDIONE(581-83-9)
• EPA Substance Registry System: 1-(4-BIPHENYLYL)-4,4,4-TRIFLUORO-1,3-BUTANEDIONE(581-83-9)

Safety Data

• Hazardous Substances Data: 581-83-9(Hazardous Substances Data)

Usage

General Description

1-(4-biphenylyl)-4,4,4-trifluoro-1,3-butanedione, also known as dibenzoylmethane, is a chemical compound used in various industrial and scientific applications. It is a yellow crystalline solid with a melting point of 76-78°C, and is commonly used as a fluorescent chemosensor for metal ions and a precursor for pharmaceuticals. It is a versatile compound with potential therapeutic effects, such as anti-inflammatory and anti-cancer properties. Additionally, it is used as a photoluminescent material in the production of organic light-emitting diodes (OLEDs) and other optoelectronic devices. Overall, 1-(4-biphenylyl)-4,4,4-trifluoro-1,3-butanedione is a valuable and multi-purpose chemical with a wide range of applications in various industries.

InChI:InChI=1/C16H11F3O2/c17-16(18,19)15(21)10-14(20)13-8-6-12(7-9-13)11-4-2-1-3-5-11/h1-9H,10H2

Upstream product

• 92-91-1 biphenyl-4-acetaldehyde 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 618068-99-8 4-(5-(biphenyl-4-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide 
• 1252678-93-5 5-Biphenyl-4-yl-1-(4-nitro-phenyl)-3-trifluoromethyl-1H-pyrazole 
• 1374744-72-5 N-[4-(5-biphenyl-4-yl-3-trifluoromethyl-pyrazol-1-yl)-phenyl]-aminosulfonamide 
• 1177469-50-9 4-(5-biphenyl-4-yl-3-trifluoromethyl-pyrazol-1-yl)-phenylamine 

Relevant articles and documents

An Integrated Continuous Flow Micro-Total Ultrafast Process System (μ-TUFPS) for the Synthesis of Celecoxib and Other Cyclooxygenase Inhibitors

Integrated continuous manufacturing has emerged as a promising device for the rapid manufacturing of active pharmaceutical ingredients (APIs). We herein report a newly designed continuous flow micro-total process system platform for the rapid manufacturing of celecoxib, a selective nonsteroidal anti-inflammatory drug. This approach has been proven generally for the synthesis of several alkyl and aryl substituted pyrazoles. In order to minimize the tedious work-up process of potential reaction intermediates/products, we have developed a continuous flow extraction and separation platform to carry out the entire reaction sequence resulting in a short residence time with good yield. The present process was further extended to gram-scale synthesis of the COX-2-related API, viz. celecoxib, in the continuous flow process.

Development of novel antibacterial agents against methicillin-resistant Staphylococcus aureus

Methicillin-resistant Staphylococcus aureus (MRSA) poses a serious threat to public health because of its resistance to multiple antibiotics most commonly used to treat infection. In this study, we report the unique ability of the cyclooxygenase-2 (COX-2) inhibitor celecoxib to kill Staphylococcus aureus and MRSA with modest potency. We hypothesize that the anti-Staphylococcus activity of celecoxib could be pharmacologically exploited to develop novel anti-MRSA agents with a distinct mechanism. Examination of an in-house, celecoxib-based focused compound library in conjunction with structural modifications led to the identification of compound 46 as the lead agent with high antibacterial potency against a panel of Staphylococcus pathogens and different strains of MRSA. Moreover, this killing effect is bacteria-specific, as human cancer cells are resistant to 46. In addition, a single intraperitoneal administration of compound 46 at 30 mg/kg improved the survival of MRSA-infected C57BL/6 mice. In light of its high potency in eradicating MRSA in vitro and its in vivo activity, compound 46 and its analogues warrant continued preclinical development as a potential therapeutic intervention against MRSA.