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Basic Information

Molecular Structure:
CAS No.:	65-49-6
Name:	4-Aminosalicylic acid
Article Data:	63

Formula:	C₇H₇NO₃
Molecular Weight:	153.137
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;
EINECS:	200-613-5
Density:	1.491 g/cm³
Melting Point:	135-145 °C(lit.)
Boiling Point:	380.8 °C at 760 mmHg
Flash Point:	184.1 °C
Solubility:	water: 2 g/L (20 °C )
Appearance:	beige powder
Hazard Symbols:	Xn,Xi,T
Risk Codes:	22-36-36/37/38-45
Safety:	26-37/39-45-53-36
Transport Information:	UN 1789 8/PG 3
PSA:	83.55000
LogP:	1.25380

Synthetic route

: 619-19-2
2-hydroxy-4-nitrobenzoic acid

: 65-49-6
4-Aminosalicylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
With sulfuric acid; sodium nitrite Eintragen der Reaktionsloesung in warme Schwefelsaeure;

: 591-27-5
m-Hydroxyaniline

: 65-49-6
4-Aminosalicylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
With carbon dioxide; potassium hydrogencarbonate

: 108-46-3
recorcinol

: 65-49-6
4-Aminosalicylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide at 260℃;

: 591-27-5
m-Hydroxyaniline

potassium dicarbonate: potassium dicarbonate

: 65-49-6
4-Aminosalicylic acid

Conditions

Conditions	Yield
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

Conditions	Yield
With water; nickel Hydrogenation;

Raw Materials

43134-76-5

298-14-6

591-27-5

17980-39-1

6018-18-4

39835-14-8

108-46-3

619-19-2

Downstream Products

345-29-9

Total:160 Page 1 of 5 1 2 3 4 5 Next>>

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History

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

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

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)	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.