4-Aminosalicylic acid
4-Aminosalicylic acid
CAS: 65-49-6
Molecular Formula: C7H7NO3
4-Aminosalicylic acid - Names and Identifiers
| Name | 4-Aminosalicylic acid |
| Synonyms | PAS 4-aminosalicylic Aminosalicylic Acid 4-Aminosalicylic acid 4-Aminosalicyclic acid FUCHSIN SULFUROUS ACID 3-Hydroxy-4-carboxyaniline 4-Amino-2-hydroxbenzoicacid 4-amino-2-hydroxy-benzoicaci 4-Amino-2-hydroxybenzoic acid 2-HYDROXY-4-AMINOBENZOIC ACID |
| CAS | 65-49-6 |
| EINECS | 200-613-5 |
| InChI | InChI=1/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11) |
4-Aminosalicylic acid - Physico-chemical Properties
| Molecular Formula | C7H7NO3 |
| Molar Mass | 153.14 |
| Density | 1.3585 (rough estimate) |
| Melting Point | 135-145 °C (lit.) |
| Boling Point | 276.03°C (rough estimate) |
| Water Solubility | 2 g/L (20 ºC) |
| Solubility | Soluble in water (2 g/l) at 20 °C, dilute sodium hydroxide, dilute nitric acid, ether |
| Appearance | White to light yellow powder |
| Color | Colorless |
| Merck | 14,477 |
| BRN | 473071 |
| pKa | 3.25(at 25℃) |
| PH | 3.5 (1g/l, H2O, 20℃) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Stability | Hygroscopic |
| Sensitive | Sensitive to light and air |
| Refractive Index | 1.5500 (estimate) |
| MDL | MFCD00007789 |
| Physical and Chemical Properties | White crystals. The melting point was 150-151 °c (decomposition). No odor or slightly acetone odor. Soluble in dilute nitric acid, dilute sodium hydroxide, acetone, sodium bicarbonate and phosphoric acid, slightly soluble in ethanol, slightly soluble in ether, insoluble in water and benzene. At 40 ° C., the aqueous solution is unstable, and carbon dioxide is decomposed to generate aminophenol. It turned brown when exposed to air. |
| Use | Pharmaceutical Intermediates, for the synthesis of anti-tuberculosis drug sodium aminosalicylate |
4-Aminosalicylic acid - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36 - Irritating to the eyes R36/37/38 - Irritating to eyes, respiratory system and skin. R45 - May cause cancer R35 - Causes severe burns R61 - May cause harm to the unborn child |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S53 - Avoid exposure - obtain special instructions before use. S36 - Wear suitable protective clothing. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| UN IDs | UN 1789 8/PG 3 |
| WGK Germany | 2 |
| RTECS | VO1225000 |
| TSCA | Yes |
| HS Code | 29225000 |
| Toxicity | LD50 orally in mice: 4 g/kg (Bavin) |
4-Aminosalicylic acid - Upstream Downstream Industry
| Raw Materials | 3-Aminophenol |
4-Aminosalicylic acid - Introduction
4-Aminosalicylic acid is an inhibitor of NF κ B.
Last Update：2022-10-16 17:27:43
4-Aminosalicylic acid - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| biological activity | 4-aminosalicylacid (Para-aminosalicylic acid, Aminosalicylic acid, 4-aminosalicylate) is an anti-tuberculosis drug, it has antibacterial activity against Mycobacterium tuberculosis. |
| uses | pharmaceutical intermediates for the synthesis of anti-tuberculosis drugs against sodium sulfasalate. Also used to analyze the reagent acid-base fluorescent indicator. pharmaceutical intermediate, used in the synthesis of anti-tuberculosis drug sodium p-aminosalicylate pharmaceutical intermediate, used in the synthesis of anti-tuberculosis drug sodium p-aminosalicylate. Also used to analyze the reagent acid-base fluorescent indicator. Pharmaceutical intermediate, used in the synthesis of antitubercular drug sodium p-aminosalicylate; As brightener, leveler and leveler for zinc plating in alkaline |
| production method | is obtained by hydroxylation of M-aminophenol. Water, M-aminophenol and sodium bicarbonate are sequentially put into the reaction tank. After carbon dioxide is introduced to replace the air, the temperature is raised to 110±1 ℃ in a closed manner, the pressure in the tank is maintained at 0.6-0.8MPa for 6 hours, and the reaction is cooled to -5 ℃, sodium sulfite was added, filtered, washed with water, and the filtrate was washed together for acidification. The filter cake was recovered from M-aminophenol and was used. The above washing filtrate was heated to 10-15 ℃, neutralized with 30-40% sulfuric acid to pH 6.4-7.0, added with appropriate amount of sodium sulfite and sodium sulfide solution, decolorized by resin, at 30 ℃, adjust the pH value to 3-40% with 30-3.5 sulfuric acid, place, spin filter, wash with water until the sulfate radical is acceptable, and spin dry to obtain p-aminosalicylic acid. P-aminosalicylic acid can also be synthesized from phenylacetic acid. Phenylacetic acid was first nitrated at 60 °c in concentrated sulfuric acid and concentrated nitric acid, then poured into ice water and filtered to precipitate 2, 4-dinitrophenylacetic acid [643-43-6]. The nitration yield was 95%. The obtained product was added to 10-fold methanol, mixed uniformly, and dried hydrogen chloride was introduced, heated to boiling, and after cooling, crystals of methyl 2, 4-dinitrophenylacetate [58605-12-2] were precipitated. The esterification yield was 80%. The esterification was dissolved in hot methanol, butyl nitrite was added, and sodium methoxide was Added. The reaction mixture was allowed to stand for several hours until a deep red precipitate was completely precipitated, and the precipitate was isolated to give an intermediate product. This was dissolved in dilute potassium hydroxide solution and acidified by addition of hydrochloric acid to make it acidic. The evolution of carbon dioxide gas precipitated 4-nitro-2-hydroxybenzonitrile. The yield was 80%. The nitrile was mixed with water, concentrated sulfuric acid and glacial acetic acid and heated to boiling to precipitate 4-nitrosalicylic acid [619-19-2]. Dissolve 4-nitrosalicylic acid in 25% sodium carbonate solution, add ferrous sulfate aqueous solution, A suitable amount of sodium carbonate solution is added, and the iron salt is separated and precipitated by heating to boiling. After filtration, the filtrate was adjusted to pH = 3 with acetic acid, and 4-aminosalicylic acid was precipitated. The product was obtained by filtration and drying. Industrial p-aminosalicylic acid content of more than 70%, chloride less than 50ppm, sulfate less than 500ppm. |
| category | toxic substances |
| toxicity grade | poisoning |
| Acute toxicity | intraperitoneal-mouse LD50: 4250 mg/kg; Oral-mouse LD50: 4000 mg/kg |
| stimulation data | eyes-rabbits 100 mg/24 h moderate |
| flammability hazard characteristics | flammability; Toxic NOx smoke from combustion |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, water mist |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 19:05:13
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Raw Materials for 4-Aminosalicylic acid