4-Aminophenylarsonic acid CAS 98-50-0
Introduction：Basic information about 4-Aminophenylarsonic acid CAS 98-50-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
4-Aminophenylarsonic acid Basic information
| Product Name: | 4-Aminophenylarsonic acid |
| Synonyms: | (4-aminophenyl)-arsonicaci;p-Arsanilic acid /4-AMinophenylarsonic acid;Arsanilic Acid (25 mg);Arsenic acid anilide;4-Arsonoaniline;NSC 2023;4-Aminobenzenearsonic Acidp-Arsanilic Acid;p-Arsanilic acid |
| CAS: | 98-50-0 |
| MF: | C6H8AsNO3 |
| MW: | 217.05 |
| EINECS: | 202-674-3 |
| Product Categories: | API;CARAFATE;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;As (Arsenic) Compounds;Classes of Metal Compounds;Semimetal Compounds;Arsenic Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks |
| Mol File: | 98-50-0.mol |
4-Aminophenylarsonic acid Chemical Properties
| Melting point | ≥300 °C(lit.) |
| Boiling point | 528.5±52.0 °C(Predicted) |
| density | 1.9571 |
| solubility | Sparingly soluble in water, soluble in concentrated mineral acids, alkalicarbonate solutions, alcohol and diethyl ether. Practically insoluble inacetone, benzene and chloroform. |
| pka | pK1: ca 2;pK2: 4.02;pK3: 8.62 (25°C) |
| form | solid |
| color | Needles from aq solns |
| Water Solubility | SLIGHTLY SOLUBLE IN COLD WATER |
| Merck | 14,792 |
| BRN | 1102334 |
| Stability: | Hygroscopic |
| Major Application | clinical testing |
| InChI | InChI=1S/C6H8AsNO3/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H,8H2,(H2,9,10,11) |
| InChIKey | XKNKHVGWJDPIRJ-UHFFFAOYSA-N |
| SMILES | [As](C1=CC=C(N)C=C1)(O)(O)=O |
| CAS DataBase Reference | 98-50-0(CAS DataBase Reference) |
| EPA Substance Registry System | p-Aminobenzenearsonic acid (98-50-0) |
Safety Information
| Hazard Codes | T,N |
| Risk Statements | 23/25-50/53 |
| Safety Statements | 20/21-28-45-60-61-28A |
| RIDADR | UN 3465 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | CF7875000 |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 29310095 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Hazardous Substances Data | 98-50-0(Hazardous Substances Data) |
| Toxicity | LD50 orally in male rats: >1000 mg/kg (Goldenthal) |
| Chemical Properties | off-white fine crystalline powder |
| Chemical Properties | p-Arsanilic acid is an off-white powder. It is slightly soluble in cold water. It is incompatible with oxidizing agents; on hazardous decomposition, p-arsanilic acid produces nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen gas, and oxides of arsenic. |
| Originator | Arsanilic acid,Fleming Laboratories, Inc. |
| Uses | 4-Aminophenylarsonic acid is an organoarsenic compound. 4-Aminophenylarsonic acid is a highly toxic contaminant and can be found in plants growing in contaminated soil. 4-Aminophenylarsonic acid was used as an additive in animal feed. It has also been used in treating dysentery in swine as well as having potential chemotherapeutic activity. |
| Uses | Arsanilic acid reacts essentially analogously to phenylarsonic acid. According to Chandelle, in the presence of relatively large amounts of accompanying ions the determination of zirconium gives more accurate results with this reagent than with phenylarsonic acid. This statement has not yet been confirmed. Nevertheless, the reagent is much more widely used than any other arsonic acid derivative. |
| Uses | manufacture of medicinal arsenicals. |
| Definition | ChEBI: Arsanilic acid is an organoarsonic acid. It is a conjugate acid of an arsanilate(1-). |
| Manufacturing Process | 342.0 g (2 mol) of 83% arsenic acid were added during 75 min to a rapidlystirred mixture of 372.5 g (4 mol) aniline and 111.0 g chlorobenzene whilethe temperature of the mixture was kept at 147°-150°C. After the addition ofarsenic acid was complete the mixture was stirred for an additional 8 h whilebeing maintained at 149°-153°C. Water was continuously removed bydistillation, and the organic phase of the distillate was continuously recycled back into the reaction mixture. At the end of that time a total of 121.0 g ofwater, containing the condensation of aniline and arsenic acid has beenremoved. The mixture was then allowed to cool to 110°C. 562.0 g (2.81 mol)of 20% sodium hydroxide were added over a 2 h period while water,chlorobenzene and excess aniline were distilled off at a temperature of from102°-113°C. The distillation was continued for an additional 2 h while thevolume of the mixture was kept at about 700 ml by the addition of water. The mixture was then diluted with water to a volume of 1400 ml and allowedto cool to 23°C. At this point, 52.0 g of by-product material, which waspredominantly tri-(p-aminophenyl)-arsineoxide, were filtered out. The pH ofthe filtrate was then brought from 8.7 to 5.1 by the addition of 1.8 mol ofhydrochloric acid while the volume of the mixture was increased to 2,200 mlby the addition of water. The mixture was stirred for 5 h at room temperatureand again filtered. 108.0 g of by-product material comprising predominantlydi-(p-aminophenyl)-arsinic acid was filtered off at this point. The pH of the filtrate was lowered to 4.5 by the addition of 0.2 mole ofhydrochloric acid, and an additional 5.0 g of by-products, the composition ofwhich was not determined, was filtered off. The filtrate was then brought to apH of 3.2 by addition of 0.6 mole of hydrochloric acid, and 128.0 g (29.5%based upon arsenic acid) of arsanilic acid were recovered as a precipitate. The arsanilic acid filtrate was combined with the by-products filtered off duringeach of the three filtration steps. 2.8 mol of hydrochloric acid were added tothe combined arsanilic acid filtrate and the mixture was heated at 80°C for 5days. Arsanilic acid was then precipitated from the remaining hydrolyzedmixture in the manner described for the primary reaction product, and anadditional 120.0 g (27.5% based on arsenic acid) were recovered. The filtratecontained 14.0 g (3.2%) of arsanilic acid which could be recovered at leastpartially in subsequent processing. Thus it can be seen from this example thatan arsanilic acid yield of 59% was obtained. |
| Therapeutic Function | Antibacterial |
| Hazard | Toxic. |
| Health Hazard | Occupational workers exposed to p-arsanilic acid develop poisoning. The symptoms include, but are not limited to, eye and skin irritation, chemical conjunctivitis and corneal damage, hyperpigmentation of the skin and, perkeratoses of plantar and palmar surfaces, primary irritation and sensitization, digestive tract irritation, gastrointestinal hypermotility, diarrhea, hepatitis, hepatocellular necrosis, central nervous system depression, cardiac disturbances, and liver and kidney damage. The target organs include the kidneys, central nervous system, liver, and cardiovascular system. After a prolonged period of exposure to arsenic compounds, including arsenical dust, workers are known to develop shortness of breath, nausea, chest pains, garlic odor, and impairment of peripheral circulation. The toxicological properties of p-arsanilic acid have not been fully investigated. |
| Safety Profile | Poison by intravenousand intraperitoneal routes. Moderately toxicby ingestion. Flammable, decomposes with heat to yield flammable vapors. Whenheated to decomposition or on contact withacid or acid fumes it emits highly toxicfumes of As and NO,. See also ARSENICCOMPOUNDS and ANILINE. |
| storage | p-Arsanilic acid should be kept stored in a tightly closed container in a cool, dry, wellventilated area. It should be kept away from incompatible materials, dust generation, excess heat, and strong oxidants. |
| Purification Methods | Crystallise it from water or ethanol/ether. POISONOUS. [Beilstein 16 I 466.] |
| Precautions | Occupational workers should wash thoroughly after using p-arsanilic acid. Any contaminated clothing should be washed before reuse. Work areas should have adequate ventilation and minimum dust generation and accumulation. Workers should avoid any kind of contact of p-arsanilic acid with the eyes, skin, clothing, ingestion or inhalation. |
4-Aminophenylarsonic acid Preparation Products And Raw materials
| Raw materials | Hydrochloric acid-->Sodium nitrite-->Sodium chloride-->Iron-->Water-->4-Nitroaniline-->Activated carbon,decolor-->Tetrachloroethylene-->ARSENIC ACID,HEMIHYDRATE-->ARSINE-->PH TEST STRIPS PH RANGE 0-14.0-->NITARSONE-->trisodium arsenate-->Sodium hydroxide-->Aniline-->Arsenic acid |
| Preparation Products | Roxarsone-->CARBARSONE-->4-HYDROXYPHENYLARSONIC ACID-->4-(2-chloroacetamido)phenylarsonic acid |
