Phenyl-4-aminosalicylate Property

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)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

Phenyl-4-aminosalicylate Chemical Properties,Usage,Production

Chemical Properties

WHITE POWDER

Originator

Pheny-Pas-Teb-Amin ,Purdue Frederick, US,1959

Uses

Phenyl 4-Aminosalicylate is a reactant in the synthesis of p-aminosalicylic ester imines with antitubercular activity.

Uses

Antibacterial(tuberculostatic).

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.]