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4-Aminosalicylic acid

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Name

4-Aminosalicylic acid

EINECS 200-613-5
CAS No. 65-49-6 Density 1.491 g/cm3
PSA 83.55000 LogP 1.25380
Solubility water: 2 g/L (20 °C ) Melting Point 135-145 °C(lit.)
Formula C7H7NO3 Boiling Point 380.8 °C at 760 mmHg
Molecular Weight 153.137 Flash Point 184.1 °C
Transport Information UN 1789 8/PG 3 Appearance beige powder
Safety 26-37/39-45-53-36 Risk Codes 22-36-36/37/38-45
Molecular Structure Molecular Structure of 65-49-6 (4-Aminosalicylic acid) Hazard Symbols HarmfulXn,IrritantXi,ToxicT
Synonyms

Salicylicacid, 4-amino- (8CI);2-Hydroxy-4-aminobenzoic acid;4-Aminosalicylicacid;Entepas;Gabbropas;Osacyl;PAS (acid);Pamisyl;Para-Pas;Paramycin;Parasal;Parasalindon;Pasnodia;Propasa;Sanipirol-4;

Article Data 63

4-Aminosalicylic acid Synthetic route

619-19-2

2-hydroxy-4-nitrobenzoic acid

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With aminomethyl polystyrene resin formic acid salt; zinc In methanol at 20℃; for 2h;96%
With ammoniummethyl polystyrene resin formate; palladium on activated charcoal In methanol at 20℃; for 5h;95%
With polymer-supported formate; magnesium In methanol at 20℃; for 3h;94%
43134-76-5

1-amino-3-acetylamino-6-carboxy-benzene

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With sulfuric acid; sodium nitrite Eintragen der Reaktionsloesung in warme Schwefelsaeure;
591-27-5

m-Hydroxyaniline

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With carbon dioxide; boric acid; potassium hydrogencarbonate at 95℃; weiteres Reagens: H2O;
With carbon dioxide; potassium hydrogencarbonate; glycerol at 130℃;
With potassium hydroxide; sodium dithionite; carbon dioxide at 100℃; under 73550.8 Torr;
With carbon dioxide; potassium carbonate at 180℃;
With salicylic acid decarboxylase from Trichosporon moniliiforme; potassium hydrogencarbonate at 30℃; for 24h; pH=8.5; aq. phosphate buffer; Enzymatic reaction; regioselective reaction;
591-27-5

m-Hydroxyaniline

A

15540-79-1

4-amino-6-hydroxyisophthalic acid

B

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With carbon dioxide; potassium hydrogencarbonate
108-46-3

recorcinol

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With ammonium carbonate at 215℃; under 154457 Torr; anschliessend Erhitzen mit Na2CO3 und CO2 auf 125grad/140 at;
With ammonium hydroxide; boric acid at 200℃; under 33097.9 Torr; anschliessend Erhitzen mit NaHCO3 und CO2 auf 110grad/20 at;
591-27-5

m-Hydroxyaniline

ammonium carbonate

ammonium carbonate

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
at 110℃;
ammonium salt of/the/ 2-hydroxy-4-nitro-benzoic acid

ammonium salt of/the/ 2-hydroxy-4-nitro-benzoic acid

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With water; nickel Hydrogenation;
dipotassium-salt of/the/ 4-amino-2-sulfo-benzoic acid

dipotassium-salt of/the/ 4-amino-2-sulfo-benzoic acid

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With potassium hydroxide at 260℃;
591-27-5

m-Hydroxyaniline

potassium dicarbonate

potassium dicarbonate

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With carbon dioxide at 85 - 90℃;
sodium-salt of/the/ 2-hydroxy-4-nitro-benzoic acid

sodium-salt of/the/ 2-hydroxy-4-nitro-benzoic acid

65-49-6

4-Aminosalicylic acid

Conditions
ConditionsYield
With water; nickel Hydrogenation;

4-Aminosalicylic acid History

1.Lehmann first tried PAS as an oral TB therapy late in 1944.

4-Aminosalicylic acid Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

4-Aminosalicylic acid Specification

The 4-Aminosalicylic acid, with the CAS registry number 65-49-6, is also known as Aminosalicylic Acid. It belongs to the product categories of Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Organic Acids; Hematology and Histology; Histology Special Stains; Electrophoresis of Glycans Stains and Dyes; Glycan Labeling and Analysis; Glycobiology; S; Stains & Dyes, A to; Amines; Aromatics; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS registry number is 200-613-5. This chemical's molecular formula is C7H7NO3 and molecular weight is 153.14. What's more, both its IUPAC name and systematic name are the same which is called 4-Amino-2-hydroxybenzoic acid. It should be stored in a sealed place and avoid light. It is manufactured by the carboxylation of 3-aminophenol. This chemical is an antibiotic used to treat tuberculosis.

Physical properties about 4-Aminosalicylic acid are: (1)ACD/LogP: 1.242; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.36; (4)ACD/LogD (pH 7.4): -1.89; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 83.55 Å2; (13)Index of Refraction: 1.691; (14)Molar Refractivity: 39.301 cm3; (15)Molar Volume: 102.673 cm3; (16)Polarizability: 15.58×10-24 cm3; (17)Surface Tension: 83.37 dyne/cm; (18)Density: 1.492 g/cm3; (19)Flash Point: 184.076 °C; (20)Enthalpy of Vaporization: 66.344 kJ/mol; (21)Boiling Point: 380.758 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

Uses of This reaction needs solvent diethyl ether at temperature of 25 °C. The reaction time is 25 min. The yield is 100 %.

 4-Aminosalicylic acid can react with diazomethane to get 4-amino-2-hydroxy-benzoic acid methyl ester.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health at low levels and it may cause inflammation to the skin or other mucous membranes. In addition, it is toxic by inhalation, in contact with skin and if swallowed. The product is irritating to eyes, respiratory system and skin. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell you should seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)c1ccc(cc1O)N
(2) InChI: InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
(3) InChIKey: WUBBRNOQWQTFEX-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 4250mg/kg (4250mg/kg)   Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie. Vol. 6B, Pg. 183, 1951.
mouse LD50 intravenous 3898mg/kg (3898mg/kg)   Antibiotiki. Vol. 18, Pg. 249, 1973.
mouse LD50 oral 4gm/kg (4000mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 2, Pg. 764, 1950.
mouse LD50 subcutaneous 4gm/kg (4000mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 2, Pg. 764, 1950.
rabbit LD50 oral 3650mg/kg (3650mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 10, Pg. 289, 1951.

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