127-85-5

Basic information

• Product Name: 4-AMINOPHENYLARSONIC ACID SODIUM SALT
• Synonyms: SODIUM 4-AMINOPHENYLARSONATE;SODIUM ARSANILATE;P-ARSANILIC ACID SODIUM SALT;(4-aminophenyl)arsonicacid,sodiumsalt[qr];(4-aminophenyl)-arsonicacimonosodiumsalt;ai3-29289-x[qr];anhydroussodiumarsanilate;anhydroussodiumarsanilate[qr]
• CAS NO: 127-85-5
• Molecular Formula: C₆H₇AsNO₃*Na
• Molecular Weight: 261.02
• EINECS: 204-869-9
• Product Categories: Organometallics;As (Arsenic) Compounds;Classes of Metal Compounds;Semimetal Compounds
• Mol File: 127-85-5.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 528.5°Cat760mmHg
• Flash Point: 273.4°C
• Appearance: /
• Density: g/cm³
• Water Solubility: Soluble in water
• Merck: 14,8578
• CAS DataBase Reference: 4-AMINOPHENYLARSONIC ACID SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINOPHENYLARSONIC ACID SODIUM SALT(127-85-5)
• EPA Substance Registry System: 4-AMINOPHENYLARSONIC ACID SODIUM SALT(127-85-5)

Safety Data

• Statements: 26/27/28
• Safety Statements: 26-36/37/39
• RIDADR: 2473
• RTECS: CF9625000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 127-85-5(Hazardous Substances Data)

Usage

Description

4-Aminophenylarsonic Acid Sodium Salt, also known as 4-ASA, is a white crystalline, odorless powder that is slightly denser than water. It is a chemical compound with potential applications in various industries due to its unique properties. However,

Uses

Used in Pharmaceutical Industry:
4-Aminophenylarsonic Acid Sodium Salt is used as an active pharmaceutical ingredient for the development of drugs targeting specific medical conditions. Its unique chemical structure allows for the creation of various drug formulations that can be utilized in the treatment of different diseases.
Used in Chemical Synthesis:
4-Aminophenylarsonic Acid Sodium Salt is used as a key intermediate in the synthesis of other chemicals, particularly those with potential applications in the pharmaceutical, agrochemical, and material science industries. Its versatility as a building block enables the development of a wide range of chemical products.
Used in Research and Development:
4-Aminophenylarsonic Acid Sodium Salt is employed as a research compound in various scientific studies, particularly in the fields of chemistry, biology, and pharmacology. Its unique properties make it an interesting subject for exploring new reactions, mechanisms, and potential applications in drug discovery and development.
Used in Analytical Chemistry:
4-Aminophenylarsonic Acid Sodium Salt can be utilized as a reagent or standard in analytical chemistry for the detection, quantification, or identification of specific compounds or elements. Its unique chemical properties make it a valuable tool in the development of new analytical methods and techniques.

Air & Water Reactions

Soluble in water.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Pharmaceutical Applications

Bechamp,teaching medicinal chemistry at the University of Montpellier, synthesised in 1863 a compound from aniline and arsenic acid, which became known later as Atoxyl. The name Atoxyl stems from its decreased toxicity. Bechamp characterised his compound as an anilide. In 1905, Thomas and Breinl showed that Atoxyl was effective in the treatment of trypanosomas, mainly Trypanosoma brucei gambiense-the cause of the African sleeping sickness, which was the main health problem around that time in Africa. Nevertheless, very high doses were required to show any pronounced effect, and as a result severe side effects such as blindness and damage to the optical nerve were common issues. Inspired by this research, Ehrlich hired the chemist Bertheim in 1905. Bertheim revised the structure of Atoxyl and the correct chemical formula was assigned. Atoxyl was identified as an p-anilinyl arsenic acid derivative on the basis of its properties to reduce Tollen’s reagent [Ag(NH3)2]+ to metallic silver and its potential use to synthesise the corresponding diazo dye.

Safety Profile

Poison by subcutaneous route. Can cause blindness. When heated to decomposition it emits very toxic fumes of As and NOx.

InChI:InChI=1/C6H8AsNO3.2Na/c8-6-3-1-5(2-4-6)7(9,10)11;;/h1-4H,8H2,(H2,9,10,11);;/q;2*+1/p-2

Synthetic route

3,3-dimethyl-oxiranecarboxylic acid amide (4417-89-4) + p-arsanilic acid monosodium salt (127-85-5) → [4-(2-carbamoyl-2-hydroxy-1,1-dimethyl-ethylamino)-phenyl]-arsonic acid

Conditions	Yield
at 150℃;

3-bromopropanamide (6320-96-3) + p-arsanilic acid monosodium salt (127-85-5) → [4-(2-carbamoyl-ethylamino)-phenyl]-arsonic acid (787494-77-3)

para-chlorotoluene (106-43-4) + p-arsanilic acid monosodium salt (127-85-5) → (4-p-toluoylamino-phenyl)-arsonic acid

4-ethoxycarbonylamino-benzoyl chloride (5180-74-5) + p-arsanilic acid monosodium salt (127-85-5) → [4-(4-ethoxycarbonylamino-benzoylamino)-phenyl]-arsonic acid (861301-81-7)

Conditions	Yield
With diethyl ether; sodium acetate
With diethyl ether; alkaline sodium acetate

2-chloro-N-(4-hydroxy-3-methoxyphenyl)acetamide (17640-79-8) + p-arsanilic acid monosodium salt (127-85-5) → N-(4-arsono-phenyl)-glycine-(4-hydroxy-3-methoxy-anilide)

Conditions	Yield
With water

2-chloro-N-(2-methyl-4-nitrophenyl)acetamide (83473-10-3) + p-arsanilic acid monosodium salt (127-85-5) → N-(4-arsono-phenyl)-glycine-(2-methyl-4-nitro-anilide)

Conditions	Yield
With water

bromo-malonic acid di-p-toluidide (333309-95-8) + p-arsanilic acid monosodium salt (127-85-5) → {4-[(bis-p-tolylcarbamoyl-methyl)-amino]-phenyl}-arsonic acid

Conditions	Yield
With ethanol

bromo-malonic acid bis-(4-bromo-anilide) (861329-81-9) + p-arsanilic acid monosodium salt (127-85-5) → (4-{[bis-(4-bromo-phenylcarbamoyl)-methyl]-amino}-phenyl)-arsonic acid

Conditions	Yield
With ethanol

dimedone (126-81-8) + p-arsanilic acid monosodium salt (127-85-5) → [4-(5,5-dimethyl-3-oxo-cyclohex-1-enylamino)-phenyl]-arsonic acid

Conditions	Yield
With water

methyl chloroacetate (96-34-4) + p-arsanilic acid monosodium salt (127-85-5) → [4-(methoxycarbonylmethyl-amino)-phenyl]-arsonic acid (5410-53-7)

Conditions	Yield
With methanol

2-Chloroethyl chloroformate (627-11-2) + p-arsanilic acid monosodium salt (127-85-5) → [4-(2-chloro-ethoxycarbonylamino)-phenyl]-arsonic acid

Conditions	Yield
With water

p-arsanilic acid monosodium salt (127-85-5) → (4-nitroso-phenyl)-arsonic acid (861529-90-0)

Conditions	Yield
With caro's acid

p-arsanilic acid monosodium salt (127-85-5) + terephthaloyl chloride (100-20-9) → N-(4-arsono-phenyl)-terephthalamic acid + (4,4'-terephthaloyldiamino-diphenyl)-bis-arsonic acid

Conditions	Yield
With sodium hydroxide

p-arsanilic acid monosodium salt (127-85-5) + ethyl chlorocarbonylacetate (36239-09-5) → [4-(2-ethoxycarbonyl-acetylamino)-phenyl]-arsonic acid

Conditions	Yield
With sodium hydroxide

p-arsanilic acid monosodium salt (127-85-5) + benzene-1,3-dicarbonyl dichloride (99-63-8) → (4,4'-isophthaloyldiamino-diphenyl)-bis-arsonic acid

Conditions	Yield
With benzene

p-arsanilic acid monosodium salt (127-85-5) + 3-nitrobenzenesulphonyl chloride (121-51-7) → [4-(3-nitro-benzenesulfonylamino)-phenyl]-arsonic acid

Conditions	Yield
With alkali

p-arsanilic acid monosodium salt (127-85-5) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → {4-[(N-acetyl-sulfanilyl)-amino]-phenyl}-arsonic acid (5410-70-8)

Conditions	Yield
With water
With sodium carbonate
With sodium hydroxide

p-arsanilic acid monosodium salt (127-85-5) + 2-nitrobenzyl chloride (610-14-0) → [4-(2-nitro-benzoylamino)-phenyl]-arsonic acid

Conditions	Yield
With sodium hydroxide; benzene at 0℃;
With xylene unter Ausschluss von Feuchtigkeit;

p-arsanilic acid monosodium salt (127-85-5) + 4-chloro-3-nitro-benzoyl chloride (38818-50-7) → [4-(4-chloro-3-nitro-benzoylamino)-phenyl]-arsonic acid (861789-64-2)

Conditions	Yield
With sodium hydroxide; benzene at 0 - 10℃;
With sodium hydroxide; toluene at -5 - 0℃;

p-arsanilic acid monosodium salt (127-85-5) + 3-chloropropyl chloroformate (628-11-5) → [4-(3-chloro-propoxycarbonylamino)-phenyl]-arsonic acid

p-arsanilic acid monosodium salt (127-85-5) + 4-nitrophenylacetyl chloride (50434-36-1) → {4-[2-(4-amino-phenyl)-acetylamino]-phenyl}-arsonic acid

Conditions	Yield
With diethyl ether; sodium acetate und Reduzieren mit Na2S2O4;

p-arsanilic acid monosodium salt (127-85-5) + β-iodo-propionamide → [4-(2-carbamoyl-ethylamino)-phenyl]-arsonic acid (787494-77-3)

p-arsanilic acid monosodium salt (127-85-5) + N-methyl-carbamic acid chloride → [4-(N'-methyl-ureido)-phenyl]-arsonic acid

Conditions	Yield
With benzene at 5℃;

p-arsanilic acid monosodium salt (127-85-5) + 3-chloromethylene-camphor → {4-[(2-oxo-bornan-3-ylidenemethyl)-amino]-phenyl}-arsonic acid

Conditions	Yield
at 120℃;

p-arsanilic acid monosodium salt (127-85-5) + 3-oxymethylene-camphor → {4-[(2-oxo-bornan-3-ylidenemethyl)-amino]-phenyl}-arsonic acid

Conditions	Yield
at 80 - 110℃;

p-arsanilic acid monosodium salt (127-85-5) + 4--benzoic acid → 4-{[N-(4-arsono-phenyl)-glycyl]-amino}-benzoic acid

Conditions	Yield
With water

p-arsanilic acid monosodium salt (127-85-5) + C-bromo-N.N'-dibenzyl-malonamide → {4-[(bis-benzylcarbamoyl-methyl)-amino]-phenyl}-arsonic acid

Conditions	Yield
With ethanol

3-formyl-(+)-camphor (87479-91-2) + p-arsanilic acid monosodium salt (127-85-5) → 3-phenyliminomethyl-camphor + 3-<4-arsono-anilinomethylene>-d-camphor + compound C27H42O2

Conditions	Yield
at 80 - 110℃;

p-arsanilic acid monosodium salt (127-85-5) → 4-aminophenylarsenoxide (1122-90-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: alkali; sulfomonoperoxoic acid 2: phenylhydrazine View Scheme

p-arsanilic acid monosodium salt (127-85-5) → N-(4-dichloroarsino-phenyl)-malonamic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous NaOH-solution 2: aqueous NaOH-solution 3: water; iodine; sulfur dioxide; hydrochloric acid View Scheme

Downstream Products

• 823813-99-6 [4-(2-hydroxy-ethylamino)-phenyl]-arsonic acid 
• 5410-60-6 (4-sulfanilylamino-phenyl)-arsonic acid 
• 861789-60-8 (4-anthraniloylamino-phenyl)-arsonic acid 
• 857802-27-8 N-(4-arsono-phenyl)-malonamic acid 
• 1122-90-3 4-aminophenylarsenoxide 
• 787494-77-3 [4-(2-carbamoyl-ethylamino)-phenyl]-arsonic acid 
• 861789-64-2 [4-(4-chloro-3-nitro-benzoylamino)-phenyl]-arsonic acid 
• 5410-70-8 {4-[(N-acetyl-sulfanilyl)-amino]-phenyl}-arsonic acid