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| | Phenyl-4-aminosalicylate Basic information |
| Product Name: | Phenyl-4-aminosalicylate | | Synonyms: | TIMTEC-BB SBB000692;PHENYL PAS;PHENYL 4-AMINOSALICYLATE;fenamisal;4-amino-2-hydroxybenzoic acid phenyl ester;PHENYL AMINOSALICYLATE;PHENYL 4-AMINOSALICYLATE(PHENYL PAS);4-Aminosalicylic acid phenyl ester | | CAS: | 133-11-9 | | MF: | C13H11NO3 | | MW: | 229.23 | | EINECS: | 205-092-8 | | Product Categories: | | | Mol File: | 133-11-9.mol |  |
| | Phenyl-4-aminosalicylate Chemical Properties |
| Melting point | 150-152 °C(lit.) | | Boiling point | 371.13°C (rough estimate) | | density | 1.2084 (rough estimate) | | refractive index | 1.5500 (estimate) | | storage temp. | -20°C Freezer | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | 8.76±0.10(Predicted) | | form | Solid | | color | Off-White | | CAS DataBase Reference | 133-11-9(CAS DataBase Reference) | | EPA Substance Registry System | Phenyl 4-aminosalicylate (133-11-9) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 |
| | Phenyl-4-aminosalicylate Usage And Synthesis |
| Chemical Properties | WHITE POWDER | | Originator | Pheny-Pas-Teb-Amin ,Purdue Frederick, US,1959 | | Uses | Antibacterial(tuberculostatic). | | Uses | Phenyl 4-Aminosalicylate is a reactant in the synthesis of p-aminosalicylic ester imines with antitubercular activity. | | Definition | ChEBI: 4-amino-2-hydroxybenzoic acid phenyl ester is a carbonyl compound. | | Manufacturing Process | 183 g of p-nitrosalicylic acid are dissolved in 564 g of phenol by heating to 140°C to 150°C on an oil bath. When all the p-nitrosalicylic acid is dissolved, 153 g of phosphorus oxychloride are run in, drop by drop, over a period of about 2 hours, while maintaining the temperature at about 150°C. The still warm mixture is run into 2 liters of water with agitation. The precipitate formed is filtered off, washed with water until phenol is removed and then dried.
There are thus obtained 250 g of 2-hydroxy-4-nitrophenylbenzoate which melts at 154°C to 155°C.
In a hydrogenation autoclave are introduced 92 g of 2-hydroxy-4nitrophenylbenzoate preceded by 200 cc of ethyl acetate; Raney nickel, obtained from 30 g of alloy, is added with 300 cc of ethyl acetate. Hydrogenation under pressure (100 to 120 kg) at ordinary temperature is carried out during a period of about 12 hours. The nickel is filtered off and the ethyl acetate is removed by distillation on the water bath under a vacuum of 300 mm. There is thus obtained 80 g of crude damp 2-hydroxy-4amnophenylbenzoate which after recrystallization from isopropyl alcohol melts at 153°C. | | Brand name | Pheny-Pas-Tebamin (Purdue Frederick). | | Therapeutic Function | Antibacterial (tuberculostatic) | | Purification Methods | Crystallise the ester from EtOH (m 155o, also 149-150.5o), aqueous EtOH (m 147-149o), or isopropanol. It is tuberculostatic.[Beilstein 13 IV 1979.] |
| | Phenyl-4-aminosalicylate Preparation Products And Raw materials |
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