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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

MSDS

• Language:English Provider:4-Amino-2-hydroxybenzoic acid phenyl ester
• Language:English Provider:SigmaAldrich

Phenyl-4-aminosalicylate Usage And Synthesis

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.]

Phenyl-4-aminosalicylate (133-11-9)Related Product Information

• 6-Aminocaproic acid
• Phenyl salicylate
• Tris(trimethylsilyl)phosphate
• PHENYL VALERATE
• Phenetidine
• Glycine
• Diphenyl ether
• 4-Aminosalicylic acid
• 4,4'-Diaminodiphenylsulfone
• 5-Aminosalicylic acid
• PHENETHYL SALICYLATE
• Pasiniazid
• Sodium 4-aminosalicylate dihydrate
• Sulfanilic acid
• 4-Aminobenzoic acid
• 4-Amino-benzenesulfonic acid monosodium salt
• METHYL 4-AMINOSALICYLATE
• PHENYL RESIN