| Identification | More | [Name]
Phenyl-4-aminosalicylate | [CAS]
133-11-9 | [Synonyms]
4-amino-2-hydroxybenzoic acid phenyl ester
fenamisal
PHENYL 4-AMINOSALICYLATE
PHENYL PAS
TIMTEC-BB SBB000692
PHENYL AMINOSALICYLATE
PHENYL 4-AMINOSALICYLATE(PHENYL PAS)
4-Aminosalicylic acid phenyl ester
Phenyl 4-amino-3-hydroxybenzoate
Phenyl p-aminosalicylate
Pheny-PAS-Tebamin
NSC-40144
p-Aminosalol
Phenyl-PAS-Tebamin
Tebamin
Tebanyl | [EINECS(EC#)]
205-092-8 | [Molecular Formula]
C13H11NO3 | [MDL Number]
MFCD00007788 | [Molecular Weight]
229.23 | [MOL File]
133-11-9.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE POWDER | [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) | [form ]
Solid | [pka]
8.76±0.10(Predicted) | [color ]
Off-White | [CAS DataBase Reference]
133-11-9(CAS DataBase Reference) | [EPA Substance Registry System]
133-11-9(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
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| Hazard Information | Back Directory | [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.] |
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