Conditions | Yield |
---|---|
With sodium hydroxide; hydrogen; palladium under 1520 - 2280 Torr; | |
With hydrogen; sodium acetate; palladium under 1520 - 2280 Torr; | |
With sodium hydroxide; iron(II) sulfate | |
With hydrogenchloride; iron at 85 - 90℃; |
anilinium arsenate
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
at 190 - 200℃; |
Conditions | Yield |
---|---|
at 190 - 200℃; beim Erhitzen von arsensaurem Anilin; |
orthoarsenic acid
aniline
A
p-aminophenylarsonic acid
B
bis-(4-amino-phenyl)-arsinous acid
Conditions | Yield |
---|---|
at 170 - 200℃; |
aniline
A
p-aminophenylarsonic acid
B
bis-(4-amino-phenyl)-arsinous acid
Conditions | Yield |
---|---|
at 180℃; |
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide | |
With iodine; acetic acid |
Conditions | Yield |
---|---|
at 170 - 200℃; |
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
at 190 - 200℃; |
4-aminophenylarsenoxide
iodine
acetic acid
p-aminophenylarsonic acid
carbarsone
A
p-aminophenylarsonic acid
B
ammonia
C
methylammonium carbonate
Conditions | Yield |
---|---|
Zers.; |
N-(4-methoxy-benzoyl)-glycine-(4-arsono-anilide)
water
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
Hydrolysis; |
[(4-amino-phenyl)-arsanediyldimercapto]-di-acetic acid
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
beim Behandeln der alkal. Loesung; |
N-(N-ethoxycarbonyl-glycyl)-glycine-(4-arsono-anilide)
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
at 85 - 95℃; |
orthoarsenic acid
aniline
A
p-aminophenylarsonic acid
B
bis-(4-amino-phenyl)-arsinic acid
Conditions | Yield |
---|---|
at 170 - 200℃; | |
In not given at 150°C;; only small amount of (NH2C6H4)2AsO(OH);; | |
In not given excess of aniline;; | |
In not given at 150°C;; only small amount of (NH2C6H4)2AsO(OH);; | |
In not given excess of aniline;; |
Conditions | Yield |
---|---|
at 180℃; |
hydrogenchloride
bis-(4-amino-phenyl)-arsinic acid
A
p-aminophenylarsonic acid
B
aniline
Conditions | Yield |
---|---|
at 100℃; untersucht wurde die Geschwindigkeit; verschiedener Konzentration.Hydrolysis; | |
at 130℃; untersucht wurde die Geschwindigkeit; verschiedener Konzentration.Hydrolysis; |
p-nitrobenzenediazonium
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: alkali; sodium arsenite 2: ferrosulfate; NaOH-solution View Scheme |
Conditions | Yield |
---|---|
In not given heating to 190°C;; | A n/a B 0% |
In not given |
Conditions | Yield |
---|---|
With hydrogenchloride; sulfur dioxide; potassium iodide In methanol at 20℃; for 0.75h; | 98% |
With hydrogenchloride; sulfur dioxide; potassium iodide In methanol; water for 0.5h; | 95% |
With hydrogenchloride; sulfur dioxide; potassium iodide In methanol; water at 0℃; for 0.5h; | 93.7% |
With hydrogenchloride; sulfur dioxide; potassium iodide In methanol; water at 20℃; for 0.5h; | |
With hydrogenchloride; sulfur dioxide; potassium iodide In methanol; water |
p-aminophenylarsonic acid
2-Bromoacetyl bromide
4-(N-(bromoacetyl)amino)phenylarsonic acid
Conditions | Yield |
---|---|
Stage #1: p-aminophenylarsonic acid With sodium carbonate In water at 4℃; for 2h; Stage #2: 2-Bromoacetyl bromide In dichloromethane; water at 0 - 20℃; for 0.6h; Stage #3: With sulfuric acid; water pH=4; | 95% |
With sodium carbonate; potassium hydroxide In dichloromethane; water for 0.25h; Cooling with ice; | 71.4% |
With sodium carbonate In water at 0 - 20℃; for 1.16667h; | |
With sodium carbonate In water at 0 - 20℃; for 1h; Cooling with ice; |
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
Stage #1: p-aminophenylarsonic acid With hydrogenchloride In water at 0℃; for 0.166667h; Stage #2: With sodium nitrite In water at 0℃; for 0.25h; Stage #3: With sodium azide In water at 0 - 20℃; for 12h; | 94% |
Conditions | Yield |
---|---|
In ethanol at 4℃; for 2h; | 93% |
p-aminophenylarsonic acid
3-Bromopropionyl chloride
4-(bromopropionamido)-phenylarsanilic acid
Conditions | Yield |
---|---|
Stage #1: p-aminophenylarsonic acid With potassium hydroxide; sodium hydrogencarbonate In water Stage #2: 3-Bromopropionyl chloride In water at 0℃; for 0.116667h; Stage #3: With sulfuric acid In water at 0℃; pH=1; | 89% |
p-aminophenylarsonic acid
2-chloropropionyl chloride
(4-(3-chloropropanamido)phenyl)arsonic acid
Conditions | Yield |
---|---|
With sodium carbonate; potassium hydroxide In dichloromethane; water Cooling with ice; | 87.58% |
Stage #1: p-aminophenylarsonic acid With sodium carbonate; potassium hydroxide In water Cooling with ice; Stage #2: 2-chloropropionyl chloride In dichloromethane; water for 0.333333h; Cooling with ice; | 87.58% |
Conditions | Yield |
---|---|
In ethanol for 4h; Cooling with ice; | 87% |
p-aminophenylarsonic acid
6,7-dimethoxy-4-chloroquinazoline
Conditions | Yield |
---|---|
With hydrogenchloride In isopropyl alcohol Heating; | 85.4% |
for 24h; Heating; | |
With hydrogenchloride In isopropyl alcohol Heating; |
p-aminophenylarsonic acid
[2,2]bipyridinyl
water
copper(II) acetate monohydrate
Conditions | Yield |
---|---|
With ammonium fluoride at 135℃; for 48h; pH=3 - 4; Autoclave; | 85% |
p-aminophenylarsonic acid
4-Chloro-2-methylthiopyrimidine
Conditions | Yield |
---|---|
With hydrogenchloride In isopropyl alcohol Heating; | 82.5% |
for 24h; Heating; | |
With hydrogenchloride In isopropyl alcohol Heating; |
Conditions | Yield |
---|---|
With NaN3; N2H4*H2O; HCl In water; N,N-dimethyl-formamide mixt. of NaVO3, NaN3, acid, H2O and DMF was stirred at 70°C untilclear soln. formed; N2H4*H2O, concd. aq. HCl were added at 70°C to pH 7.3; stirred for 15 min; filtered; cooled to room temp.; filtered after 1 d; kept for 2 d; | 82% |
Conditions | Yield |
---|---|
Stage #1: p-aminophenylarsonic acid With ammonium 2-sulfanylacetate In ethanol at 55℃; for 1h; Stage #2: 1.3-propanedithiol In ethanol for 0.5h; | 80% |
Stage #1: p-aminophenylarsonic acid With ammonium 2-sulfanylacetate at 50℃; for 2h; Stage #2: 1.3-propanedithiol | 52% |
Stage #1: p-aminophenylarsonic acid With ammonium thioglycolate at 50℃; for 2h; Stage #2: 1.3-propanedithiol | 52% |
Stage #1: p-aminophenylarsonic acid With ammonium 2-sulfanylacetate at 50℃; for 0.5h; Stage #2: 1.3-propanedithiol | 35% |
Stage #1: p-aminophenylarsonic acid With ammonium 2-sulfanylacetate at 50℃; for 0.5h; Stage #2: 1.3-propanedithiol | 35% |
p-aminophenylarsonic acid
[2,2]bipyridinyl
cobalt(II) diacetate tetrahydrate
Conditions | Yield |
---|---|
With ammonium fluoride In water at 135℃; for 48h; pH=4; Autoclave; | 75% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium carbonate In dichloromethane; water at 20℃; for 65h; | 75% |
p-aminophenylarsonic acid
6-chloropurine
6-(4'-phenylarsonic acid)aminopurine
Conditions | Yield |
---|---|
With hydrogenchloride In isopropyl alcohol Heating; | 71.3% |
for 24h; Heating; | |
With hydrogenchloride In isopropyl alcohol Heating; |
Conditions | Yield |
---|---|
In methanol for 24h; | 71% |
Conditions | Yield |
---|---|
In water at 100℃; for 1h; | 71% |
p-aminophenylarsonic acid
N,N-dimethyl-2,3-dihydroxybenzamide
bis(2,3,7,8,b,h)-(1NN-dimethylamidobenzo)-5-arsa-5-paraaminophenyl 1,4,6,9-tetraoxaspiro(4,4)nonane
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 70% |
In acetic anhydride for 0.333333h; Heating; |
p-aminophenylarsonic acid
N,N-Diethyl-2,3-dihydroxy-benzamide
bis(2,3,7,8,b,h)-(1NN-diethylamidobenzo)-5-arsa-5-paraaminophenyl 1,4,6,9-tetraoxaspiro(4,4)nonane
Conditions | Yield |
---|---|
In benzene for 48h; Heating; | 70% |
In acetic anhydride for 0.333333h; Heating; |
Conditions | Yield |
---|---|
Stage #1: p-aminophenylarsonic acid With ammonium 2-sulfanylacetate In ethanol at 55℃; for 1h; Stage #2: succimer In ethanol for 0.5h; | 68% |
p-aminophenylarsonic acid
phenol
4-(4'-hydroxyphenylazo)phenylarsonic acid
Conditions | Yield |
---|---|
62% |
Conditions | Yield |
---|---|
With ammonium fluoride In water at 135℃; for 48h; pH=4; Autoclave; | 60% |
p-aminophenylarsonic acid
ethane-1,2-dithiol
4-(1,3,2-dithiocycloarsenic-2-yl)aniline
Conditions | Yield |
---|---|
Stage #1: p-aminophenylarsonic acid With ammonium 2-sulfanylacetate In ethanol at 55℃; for 1h; Stage #2: ethane-1,2-dithiol In ethanol for 0.5h; | 60% |
Stage #1: p-aminophenylarsonic acid With phenylhydrazine In methanol Reflux; Stage #2: ethane-1,2-dithiol In ethanol for 0.333333h; Reflux; | 34% |
Stage #1: p-aminophenylarsonic acid With phenylhydrazine In methanol for 1.5h; Reflux; Stage #2: ethane-1,2-dithiol In ethanol for 0.333333h; Reflux; | 1.8 g |
Conditions | Yield |
---|---|
Stage #1: p-aminophenylarsonic acid With ammonium 2-sulfanylacetate at 50℃; for 0.5h; Stage #2: 2,3-dimercaptopropanol | 58% |
p-aminophenylarsonic acid
2,2':6,2''-terpyridine
[Cu2(OAc)4(H2O)2]
water
Conditions | Yield |
---|---|
With H2SO4 In water High Pressure; mixt. of MoO3, Cu acetate, terpyridine, p-arsanilic acid, H2O (mole ratio = 2.51:1.00:1.00:1.25:1253) and concd. H2SO4 stirred briefly, heated at 150°C for 48 h under autogenous pressure; crystals isolated; | 55% |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; water at 100℃; for 1h; | 55% |
p-aminophenylarsonic acid
N,N-dimethyl-formamide
Conditions | Yield |
---|---|
With ammonium acetate; N2H4*H2SO4; acetic acid In water; N,N-dimethyl-formamide to soln. (NH4)6Mo7O24*4H2O and AcONH4 in water-DMF at room temp. N2H4*H2SO4 was added, stirred for 5 min, p-arsanic acid was added, stirred for 10 min, pH was adjusted to 4.9 with aq. AcOH, kept for 5-7 days; elem. anal.; | 53% |
p-aminophenylarsonic acid
Conditions | Yield |
---|---|
With phenylhydrazine In methanol for 1h; Reflux; | 53% |
With phenylhydrazine In methanol for 1h; Reflux; | 53% |
With phenylhydrazine for 2.5h; Reflux; | 40% |
Conditions | Yield |
---|---|
In ethanol for 4h; Cooling with ice; | 51% |
p-aminophenylarsonic acid
[2,2]bipyridinyl
nickel(II) acetate tetrahydrate
Conditions | Yield |
---|---|
With ammonium fluoride In water at 135℃; for 48h; pH=4; Autoclave; | 50% |
Molecular Formula: C6H8AsNO3
Molar mass: 217.05 g/mol
EINECS: 202-674-3
Flash Point: 273.4 °C
Boiling Point: 528.5 °C at 760 mmHg
Vapour Pressure: 5.34E-12 mmHg at 25°C
Melting point: ≥300 °C(lit.)
Water solubility: Slightly soluble
Appearance: Off-white fine crystalline powder
Product categories: As (Arsenic) Compounds;Semimetal Compounds;Classes of Metal Compounds
Structure of Arsanilic acid (98-50-0):
H-Bond Donor: 3
H-Bond Acceptor: 4
IUPAC Name: (4-Aminophenyl)arsonic acid
Canonical SMILES: C1=CC(=CC=C1N)[As](=O)(O)O
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
Arsanilic acid (98-50-0) was initially used in medicine to treat simple skin diseases. In 1905, H.W. Thomas and A. Breinl, reported that atoxyl was active against the trypanosomes of sleeping sickness. The effect was however not very pronounced and the necessary dosage was so high that toxic side effects far outweighed the benefits. Nevertheless, the discovery of arsanilic acid's activity against trypanosomes was the basis for a major advance by the bacteriologist Paul Ehrlich.The result of this collaboration was the discovery of the drug Salvarsan in 1909, which also was later abandoned but which accelerated the growth of medicinal chemistry.
Arsanilic acid (98-50-0) was used as a drug in the late 19th and early 20th centuries but is now considered prohibitively toxic.
Arsanilic acid (98-50-0) was first reported in 1859 by Antoine Béchamp.The original synthesis, which involved the reaction of aniline and arsenic acid, remains useful today.Béchamp optimistically chose the name Atoxyl, referring to its reduced toxicity compared to arsenic.
1. | orl-rat LD50:>1000 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 18 (1971),185. | ||
2. | ipr-rat LDLo:400 mg/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 80 (1944),393. | ||
3. | ipr-mus LD50:248 mg/kg | APFRAD Annales Pharmaceutiques Francaises. 37 (1979),483. | ||
4. | ivn-mus LD50:100 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#06774 . |
IARC Cancer Review: Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 23 (1980),p. 39.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. Arsenic and its compounds are on the Community Right-To-Know List.
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Flammable, decomposes with heat to yield flammable vapors. When heated to decomposition or on contact with acid or acid fumes it emits highly toxic fumes of As and NOx. See also ARSENIC COMPOUNDS and ANILINE.
Hazard Codes: T,N
Risk Statements:
23: Toxic by inhalation
25: Toxic if swallowed
50: Very Toxic to aquatic organisms
53: May cause long-term adverse effects in the aquatic environment
Safety Statements:
20: When using, do not eat or drink
21: When using, do not smoke
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
28A After contact with skin, wash immediately with plenty of water.
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60: This material and/or its container must be disposed of as hazardous waste
61: Avoid release to the environment. Refer to special instructions safety data sheet
OSHA PEL: TWA 0.5 mg(As)/m3
ACGIH TLV: BEI: 35 μ (As)/L inorganic arsenic and methylated metabolites in urine
For occupational chemical analysis use NIOSH: Arsenic, Organo-, 5022.
Arsanilic acid (98-50-0)is the organoarsenic compound also called p-aminophenylarsenic acid ; 4-Aminobenzenearsonic acid ; 4-Arsanilic acid, Atoxyl ; 4-Aminophenylarsonic acid.It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.
In addition, it is not compatible with strong oxidizing agents, and you must not take it with incompatible materials.And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide, oxides of arsenic, oxides of nitrogen.
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