36330-85-5

Basic information

• Product Name: Fenbufen
• Synonyms: FENBUFEN;GAMMA-OXO-[1,1'-BIPHENYL]-4-BUTANOIC ACID;GAMMA-OXO(1,1'-BIPHENYL)-BUTANOIC ACID;4-(4-BIPHENYL)-4-OXOBUTYRIC ACID;4-(4-BIPHENYLYL)-4-OXOBUTYRIC ACID;3-(4-PHENYLBENZOYL)PROPIONIC ACID;1’-biphenyl)-4-butanoicacid,gamma-oxo-(;3-(4-biphenylylcarbonyl)-propionicaci
• CAS NO: 36330-85-5
• Molecular Formula: C₁₆H₁₄O₃
• Molecular Weight: 254.28
• EINECS: 252-979-0
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;COLOFAC
• Mol File: 36330-85-5.mol
• Article Data: 48

Chemical Properties

• Melting Point: 184-187 °C(lit.)
• Boiling Point: 357.5°C (rough estimate)
• Flash Point: 252.3 °C
• Appearance: White solid
• Density: 1.1565 (rough estimate)
• Vapor Pressure: 1.21E-09mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Very slightly soluble in water, slightly soluble in acetone, in ethanol (96 per cent) and in methylene chloride.
• PKA: pKa 4.3(H2O tunde?ned Iunde?ned) (Uncertain)
• Water Solubility: 2.212mg/L(25 oC)
• Merck: 13,3990
• CAS DataBase Reference: Fenbufen(CAS DataBase Reference)
• NIST Chemistry Reference: Fenbufen(36330-85-5)
• EPA Substance Registry System: Fenbufen(36330-85-5)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 28-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DV1761000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 36330-85-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Originator

Cinopal,Cyanamid,Italy,1976

Uses

Different sources of media describe the Uses of 36330-85-5 differently. You can refer to the following data:
1. Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory
2. muscle relaxant (smooth)

Manufacturing Process

135 g of aluminum chloride is dissolved in 500 ml of nitrobenzene, the solution being held below 10°C by external cooling. A finely ground mixture of 50 g of succinic anhydride and 75 g of biphenyl is added to the stirred solution, the temperature being held below 10°C. It is then held at room temperature for four days. After pouring the reaction mixture into a solution of 150 ml of concentrated hydrochloric acid in 1 liter of ice water, the nitrobenzene is removed by steam distillation. The solid is collected, dissolved in 4 liters of 3% hot sodium carbonate solution, clarified, and reprecipitated by the addition of excess 6N sulfuric acid solution. The crude product is collected, dried, and recrystallized from ethanol to give the pure subject compound, MP 185°C to 187°C.

Therapeutic Function

Antiinflammatory

General Description

Fenbufen belongs to the class of non-steroidal anti-inflammatory drugs, widely used as an antipyretic and analgesic in medical applications. Its mode of action involves the inhibition of cyclooxygenase enzyme and thereby prevents the synthesis of certain prostaglandins.

Safety Profile

Poison by ingestion,intraperitoneal, and subcutaneous routes. Human systemiceffects by ingestion: cough, sweating, body temperature.An experimental teratogen. Other experimentalreproductive effects. An anti-inflammatory agent. Whenheated to decomposi

InChI:InChI=1/C16H14O3/c17-15(10-11-16(18)19)14-8-6-13(7-9-14)12-4-2-1-3-5-12/h1-9H,10-11H2,(H,18,19)/p-1

Upstream product

• 108-30-5 succinic acid anhydride 
• 92-52-4 biphenyl 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 6340-79-0 4-oxo-4-(4-bromophenyl)butanoic acid 
• 143-66-8 sodium tetraphenyl borate 
• 1230-54-2 ethyl 4-(4-phenylphenyl)-4-oxobutyrate 
• 35288-13-2 3-(4-cyclohexylbenzoyl)propionic acid 
• 92-66-0 4-bromo-1,1'-biphenyl 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 6057-60-9 4-(4-phenylphenyl)butanoic acid 
• 54011-27-7 methyl 4-([1,1'-biphenyl]-4-yl)-4-oxobutanoate 
• 20637-07-4 methyl 4-{[1,1'-biphenyl]-4-yl}butanoate 
• 3984-34-7 4-(4-chlorophenyl)-4-oxobutanoic acid 

Downstream Products

• 92-92-2 biphenyl-4-carboxylic acid 
• 40885-19-6 5-(1,1'-biphenyl)-4-yldihydro-2(3H)-furanone 
• 1365358-51-5 6-biphenyl-4-yl-(2-indol-1-ylethyl)-4,5-dihydropyridazin-3(2H)-one 
• 1456921-54-2 6-biphenyl-4-yl-2-(2-benzotriazol-1-ylethyl)-4,5-dihydropyridazin-3(2H)-one 
• 264199-97-5 5-Biphenyl-4-yl-3-[1-(2-chloro-phenyl)-meth-(Z)-ylidene]-3H-furan-2-one 
• 63472-14-0 5-([1,1'-biphenyl]-4-yl)-5-methyldihydrofuran-2(3H)-one 
• 41526-73-2 7-phenyl-3,4-dihydronaphthalen-1(2H)-one 

Relevant articles and documents

Phospholipid bicelles that align with their normals parallel to the magnetic field

We have recently reported phospholipid bicelles (bilayered micelles) that have positive anisotropy of the magnetic susceptibility and align with their normals parallel to an external magnetic field [J. Am. Chem. Soc. 2001, 123, 1537]. Improvements have been made via the synthesis of a new phospholipid, 1-dodecanoyl-2-(4-(4-biphenyl)butanoyl)-sn-glycero-3-phosphocholine (DBBPC). Bicelles can be formed by mixing DBBPC with a short-chain phospholipid, 1,2-dihexanoyl-sn-glycero-3-phosphocholine (DHPC) in a ratio between 5.1:1 and 6.5:1 in an aqueous medium. The 31P NMR spectra clearly show that these bicelles align with their principal axes parallel to the magnetic field within a wide temperature range. The 31P chemical shifts indicate that the conformation of the polar headgroup in these bicelles may be different from that in common bicelles. The phase behavior of a mixture of DBBPC/DHPC with 6:1 mole ratio was investigated in the temperature range of 10-75 °C using 31P, 2H, and 23Na NMR. At lower temperatures (10-54 °C), the system is dominated by the bicellar phase. At higher temperatures (54-75 °C), isotropic micelles are formed and coexist with the bicelles. The partial alignment of maltotriose in the DBBPC/ DHPC system was studied at three temperatures, and the 1H-13C dipolar coupling constants are compared with those obtained for two other bicelle solutions.

Nickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes

Herein, we disclose a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines by the nickel-catalyzed cross-coupling of halostibines with organic halides. The synthesized Sb-aryl stibines couple with aryl halides to give biaryls efficiently via palladium catalysis. Sequential reactions of stibines with polyhalogenated arenes bearing active C–I/C–Br sites and inactive C–Cl sites successfully proceeded, resulting in the formation of a variety of complex molecules with good site selectivity. Drugs such as diflunisal and fenbufen, as well as a fenofibrate derivative, were synthesized on gram scales in good yields, together with the high recovery of chlorostibine. Furthermore, catalytic mechanisms are proposed based on the results of control experiments.

Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines

The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylaminesviachiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids andC-alkynylN-BocN,O-acetals as easily availableC-alkynyl imine precursors has been demonstrated here, affording a broad scope of β-ketoN-Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97?:?3 er).

Synthesis, anti-convulsant activity and molecular docking study of novel thiazole pyridazinone hybrid analogues

Pyridazinone analogues have been known to be potential candidates for anticonvulsant agents. We have identified several pyridazinone-based anticonvulsant agents. As a continuation to our previous research, a series of hybrid pyridazinone-thiazole connected through amide linkage were designed and synthesized. Among these, compound SP-5F demonstrated significant anticonvulsant activity with median effective dose of 24.38 mg/kg (MES) and 88.23 mg/kg (scPTz). Results of GABA estimation showed a marked increase in the GABA level when compared with control. Molecular docking studies at the active site of GABA receptor, further confirmed the GABA modulatory effects of SP-5F.