Fenbufen CAS 36330-85-5
Introduction：Basic information about Fenbufen CAS 36330-85-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Fenbufen 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;cl82204;diphenyl-4-gamma-oxo-gamma-butyricacid |
| CAS: | 36330-85-5 |
| MF: | C16H14O3 |
| MW: | 254.29 |
| EINECS: | 252-979-0 |
| Product Categories: | COLOFAC;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals |
| Mol File: | 36330-85-5.mol |
Fenbufen Chemical Properties
| Melting point | 184-187 °C (lit.) |
| Boiling point | 357.5°C (rough estimate) |
| density | 1.1565 (rough estimate) |
| refractive index | 1.5600 (estimate) |
| storage temp. | 2-8°C |
| 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) |
| form | Solid |
| color | White to off-white |
| Water Solubility | 2.212mg/L(25 ºC) |
| Merck | 13,3990 |
| Major Application | forensics and toxicology pharmaceutical (small molecule) veterinary |
| InChI | 1S/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) |
| InChIKey | ZPAKPRAICRBAOD-UHFFFAOYSA-N |
| SMILES | OC(=O)CCC(=O)c1ccc(cc1)-c2ccccc2 |
| EPA Substance Registry System | [1,1'-Biphenyl]-4-butanoic acid, .gamma.-oxo- (36330-85-5) |
Safety Information
| Hazard Codes | T |
| Risk Statements | 25 |
| Safety Statements | 28-45 |
| RIDADR | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | DV1761000 |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 2918300090 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral |
| Toxicity | LD50 in various strains of mice, rats (mg/kg): 795-1673, 200-720 orally; 506-811, 265-575 i.p. (Bolte) |
| Description | Fenbufen has been found to be an effective, well-tolerated drug for the treatment ofrheumatoid arthritis, osteoarthritis, and ankylosing spondylitis. Fenbufen is prepared by the Friedel-Crafts (aluminum chloride – nitrobenzene)acylation of biphenyl with succinic anhydride. The compound is metabolizedin humans first to 4-hydroxy-4-biphenylbutyricacid (tmax 2.5 h) then to 4-biphenyl acetic acid(tmax 7.5 h). Both metabolites are more activethan fenbufen itself and circulate for severalhours (t1/2 10 h). This slow conversion of fenbufen to active metabolites having relativelylong plasma half-lives allows for once a day dosing with this agent. |
| Chemical Properties | White Solid |
| Originator | Cinopal,Cyanamid,Italy,1976 |
| Uses | Cyclo-oxygenase inhibitor; analgesic; anti-inflammatory |
| Uses | muscle relaxant (smooth) |
| Definition | ChEBI: Fenbufen is a member of biphenyls and a 4-oxo monocarboxylic acid. It has a role as a non-steroidal anti-inflammatory drug. |
| Manufacturing Process | 135 g of aluminum chloride is dissolved in 500 ml of nitrobenzene, thesolution being held below 10°C by external cooling. A finely ground mixture of50 g of succinic anhydride and 75 g of biphenyl is added to the stirredsolution, the temperature being held below 10°C. It is then held at roomtemperature for four days. After pouring the reaction mixture into a solutionof 150 ml of concentrated hydrochloric acid in 1 liter of ice water, thenitrobenzene is removed by steam distillation. The solid is collected, dissolvedin 4 liters of 3% hot sodium carbonate solution, clarified, and reprecipitatedby the addition of excess 6N sulfuric acid solution. The crude product iscollected, dried, and recrystallized from ethanol to give the pure subjectcompound, 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. |
| Trade name | Clincopal (Lederle, Spain),Lederfen (Lederle, UK), Napanol (Lederle,Japan). |
| 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 |
| References | [1] Organic Letters, 2016, vol. 18, # 3, p. 504 - 507 [2] Organic Preparations and Procedures International, 1995, vol. 27, # 5, p. 550 - 552 [3] Chemistry Letters, 2015, vol. 44, # 11, p. 1503 - 1505 [4] Organic Process Research and Development, 2004, vol. 8, # 2, p. 291 - 292 [5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 8, p. 614 - 619 |
Fenbufen Preparation Products And Raw materials
| Raw materials | Biphenyl-->Succinic anhydride-->Aluminum chloride-->4-(4-Biphenylyl)butanoic acid methyl ester-->4-cyclohexyl-gamma-oxobenzenebutyric acid-->Fenbufen Methyl Ester-->ETHYL 4-(4-BIPHENYL)-4-OXOBUTYRATE-->3-(4-Chlorobenzoyl)propionic acid-->3-(4-BROMOBENZOYL)PROPIONIC ACID-->Sodium tetraphenylboron-->4-Biphenylcarbonyl chloride-->Phenylboronic acid-->Nitrobenzene-->4-Bromobiphenyl |
| Preparation Products | 4-(4-BIPHENYLYL)BUTYRIC ACID |
