121-19-7

Hazards Identification

Pictogram(s):

Signal:

Danger

GHS Hazard Statements:

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]
H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes:

P261, P264, P270, P271, P273, P301+P316, P304+P340, P316, P321, P330, P391, P403+P233, P405, and P501

Hazard Classes and Categories:

Acute Tox. 3 (100%)
Aquatic Acute 1 (100%)
Aquatic Chronic 1 (100%)

Hazards Summary:

May cause arsenic poisoning; [CAMEO] Almost nothing is known regarding health effects of organic arsenic compounds in humans. Studies in animals show that some simple organic arsenic compounds are less toxic than inorganic forms. Ingestion of methyl and dimethyl compounds can cause diarrhea and damage to the kidneys. [ATSDR ToxProfiles] Marginally increased incidence of pancreatic adenomas in 2-year feeding studies of rats; Repeated oral doses (0.87-5.8 mg/kg/day for 1 month) to pigs causes neurotoxicity with axonal degeneration and partial paralysis. Causes kidney injury in animals in acute toxicity testing; Oral LD50 (rat) = 81 mg/kg; [HSDB] In order of decreasing toxicity are inorganic trivalent, organic trivalent, inorganic pentavalent, and organic pentavalent compounds. [Sullivan, p. 858] Arsenic and arsenic compounds are carcinogenic in humans (not necessarily to all individuals chemicals within the group). [IARC] May cause irritation; Targets pancreas, kidneys, and nerves; Effects in high-dose animal studies include diffuse hepatitis (hepatocellular necrosis) and kidney damage; [MSDSonline] See Arsanilic acid.

Usage

Uses

Used in Anti-infective Applications:
Roxarsone is used as an anti-infective agent for its ability to prevent and treat infections in various contexts.
Used as a Preservative:
Roxarsone is utilized as a preservative to prevent spoilage and extend the shelf life of products.
Used in Poultry Industry:
Roxarsone is used as a feed additive for chickens to aid in the prevention of coccidiosis, a disease caused by the protozoa Eimeria tenella and E. necatrix.
Used in Chemical Synthesis:
Roxarsone was formerly used in the manufacture of arsphenamines, which are a class of chemical compounds, and as a reagent for zirconium, an element used in various industrial applications.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

May be sensitive to light and elevated temperatures on long-term storage. Roxarsone puffs up and deflagrates on heating. Incompatible with strong oxidizers and strong acids. Forms mono-, di-, and trisodium salts.

Hazard

Toxic by ingestion, highly toxic.

Fire Hazard

Flash point data are not available for Roxarsone ; however, Roxarsone is probably combustible.

Purification Methods

It crystallises from water and is used for the spectroscopic detection of Zn. [Beilstein 16 II 468, 16 III 1073, 16 IV 1188.]

InChI:InChI=1/C6H6AsNO6/c9-6-2-1-4(7(10,11)12)3-5(6)8(13)14/h1-3,9H,(H2,10,11,12)

Synthetic route

4-hydroxyphenylarsonic acid (98-14-6) → roxarsone (121-19-7)

Conditions	Yield
With nitric acid
With sulfuric acid; nitric acid at 0 - 10℃;

phenol (108-95-2) → roxarsone (121-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 2: concentrated sulfuric acid; nitric acid / 0 - 10 °C View Scheme

(4-amino-3-nitro-phenyl)-arsonic acid (5440-06-2) → roxarsone (121-19-7)

Conditions	Yield
With potassium hydroxide at 80℃;

(4-dimethylamino-3-nitro-phenyl)-arsonic acid (861528-00-9) → roxarsone (121-19-7)

Conditions	Yield
With sodium hydroxide at 85℃;

(4-anilino-3-nitro-phenyl)-arsonic acid (741258-62-8) → roxarsone (121-19-7)

Conditions	Yield
With sodium hydroxide

diazotized 2-nitro-4-amino-phenol → roxarsone (121-19-7)

Conditions	Yield
With trisodium arsenite in alkal. Loesung;

sulfuric acid (7664-93-9) + 4-hydroxyphenylarsonic acid (98-14-6) + nitric acid (1 mol) → roxarsone (121-19-7)

Conditions	Yield
at 0 - 10℃;

(4-chloro-3-nitro-phenyl)-arsonic acid (5430-08-0) → roxarsone (121-19-7)

Conditions	Yield
With potassium hydroxide

4-chlorobenzenearsonic acid (5440-04-0) → roxarsone (121-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3+H2SO4 2: KOH-solution View Scheme

arsacetin (618-22-4) → roxarsone (121-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3+H2SO4 / beim Nitrieren 2: KOH-solution / 80 °C View Scheme

(4-dimethylamino-phenyl)-arsonic acid (91484-30-9) → roxarsone (121-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial acetic acid; nitric acid / 25 °C 2: NaOH-solution / 85 °C View Scheme

(4-bromo-3-nitro-phenyl)-arsonic acid (860602-62-6) → roxarsone (121-19-7)

Conditions	Yield
durch Einw. von Alkali;

(4-iodo-3-nitro-phenyl)-arsonic acid (873985-38-7) → roxarsone (121-19-7)

Conditions	Yield
durch Einw. von Alkali;

p-iodophenylarsonic acid (6324-92-1) → roxarsone (121-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Analog der vorangehenden Verbindung /BRN= 3318376/ 2: durch Einw. von Alkali View Scheme

(4-bromophenyl)arsonic acid (55048-80-1) → roxarsone (121-19-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Analog der vorangehenden Verbindung /BRN= 3317611/ 2: durch Einw. von Alkali View Scheme

(4-amino-3-nitro-phenyl)-arsonic acid (5440-06-2) + KOH-solution → roxarsone (121-19-7)

Conditions	Yield
at 80℃;

(4-dimethylamino-3-nitro-phenyl)-arsonic acid (861528-00-9) + furan-2,3,5(4H)-trione pyridine (1:1) → roxarsone (121-19-7)

Conditions	Yield
at 85℃;

(4-chloro-3-nitro-phenyl)-arsonic acid (5430-08-0) + KOH-solution → roxarsone (121-19-7)

(4-bromo-3-nitro-phenyl)-arsonic acid (860602-62-6) + alkaline solution → roxarsone (121-19-7)

(4-iodo-3-nitro-phenyl)-arsonic acid (873985-38-7) + NaOH-solution (25 percent ) → roxarsone (121-19-7)

GdCl3*7H2O + roxarsone (121-19-7) → [Gd(4-hydroxy-3-nitrophenylarsonic acid-3H)(H2O)2]

Conditions	Yield
In water High Pressure; GdCl3*7H2O, arsonic acid in deionized water with pH about 3.4 (1 M NaOH)at 150°C for 5 days; elem. anal.;	89%

roxarsone (121-19-7) + silver(I) acetate (563-63-3) + acetonitrile (75-05-8) → [Ag3(3-NO2-4-OH-C6H3-AsO3H)(3-NO2-4-OH-C6H3-AsO3)]

Conditions	Yield
at 100℃; for 96h; Temperature; Concentration; High pressure; Autoclave;	84%

ammonium heptamolybdate tetrahydrate + roxarsone (121-19-7) → 4NH4(1+)*(Mo4O10(HOC6H3(NO2)AsO3)4)(4-)*2H2O=(NH4)4(Mo4O10(HOC6H3(NO2)AsO3)4)*2H2O

Conditions	Yield
With ammonium acetate; N2H4*H2SO4; acetic acid In water to soln. (NH4)6Mo7O24*4H2O and AcONH4 in water at room temp. N2H4*H2SO4 was added, 4-hydroxy-3-nitrophenylarsonic was added, stirred for 10 min,pH was adjusted to 3.9 with aq. AcOH, kept for 3 weeks; ppt. was collected and washed with cold water; elem. anal.;	75%

neodymium(III) chloride hexahydrate + roxarsone (121-19-7) + sodium oxalate (62-76-0) → [Nd2(4-hydroxy-3-nitrophenylarsonic acid-2H)2(oxalato)(H2O)2]

Conditions	Yield
With NaOH In water High Pressure; NbCl3*6H2O was added to a soln. of arsonic acid in water (pH 3.0, 1 M NaOH), stirring for a few min, Na2C2O4 was added, heated in autoclave at 170°C for 4 days, slowly cooled to room temp.; elem. anal.;	75%

roxarsone (121-19-7) + silver(I) acetate (563-63-3) + acetonitrile (75-05-8) → [Ag2(3-NO2-4-OH-C6H3-AsO3)]

Conditions	Yield
at 100℃; for 96h; High pressure; Autoclave;	73%

samarium(III) chloride hexahydrate + roxarsone (121-19-7) + sodium oxalate (62-76-0) → [Sm2(4-hydroxy-3-nitrophenylarsonic acid-2H)2(oxalato)(H2O)2]

Conditions	Yield
With NaOH In water High Pressure; SmCl3*6H2O was added to a soln. of arsonic acid in water (pH 3.0, 1 M NaOH), stirring for a few min, Na2C2O4 was added, heated in autoclave at 170°C for 4 days, slowly cooled to room temp.; elem. anal.;	71%

tetra-n-butyldi-n-propoxydistannoxane (1218909-09-1) + roxarsone (121-19-7) → [n-Bu2Sn(4-OH-3-NO2-C6H3AsO3)]n

Conditions	Yield
In methanol; chloroform mixt. of tin complex and arsonic acid was stirred in CHCl3/MeOH (1:3, v/v)for 6 h; filtered, concd. by slow evapn. for 1 week, elem. anal.;	11%

roxarsone (121-19-7) + mercury(II) diacetate (1600-27-7) → 5-arsono-2-hydroxy-3-nitro-phenylmercury (1+); acetate

Conditions	Yield
With sodium hydroxide

roxarsone (121-19-7) → 4-iodo-2-nitrophenol (21784-73-6)

Conditions	Yield
With sulfuric acid; potassium iodide

roxarsone (121-19-7) → 3-amino-4-hydroxyphenylarsonic acid (2163-77-1)

Conditions	Yield
With hydrogenchloride bei der elektrolytischen Reduktion an Platin-, Kupfer- oder Nickelkathoden;
With alkali bei der elektrolytischen Reduktion an Platin-, Kupfer- oder Nickelkathoden;
With sodium hydroxide; D-glucose at 50 - 60℃;

roxarsone (121-19-7) → 3-amino-4-hydroxyphenylarsonic acid (2163-77-1) + (4,4'-dihydroxy-3,3'-azoxy-diphenyl)-bis-arsonic acid

Conditions	Yield
With hydrogenchloride; copper bei der elektrolytischen Reduktion;
With hydrogenchloride; nickel bei der elektrolytischen Reduktion;
With hydrogenchloride; platinum bei der elektrolytischen Reduktion;

roxarsone (121-19-7) → 2-Amino-4-arsino-phenol

Conditions	Yield
bei der elektrolytischen Reduktion an einer Quecksilber-Kathode in saurer Loesung je nach der Saeurerkonzentration;
With sulfuric acid at 25 - 30℃; durch elektrolytische Reduktion an einer Quecksilber-Kathode;
With hydrogenchloride at 25 - 30℃; durch elektrolytische Reduktion an einer Quecksilber-Kathode;
With hydrogenchloride; zinc

roxarsone (121-19-7) → 4-Arsenoso-2-nitro-phenol (102107-61-9)

Conditions	Yield
With hydrogen iodide; sulphurous acid
Multi-step reaction with 2 steps 1: hydrogenchloride; potassium iodide; sulfur dioxide / methanol; water / 0.5 h 2: ammonium hydroxide / methanol; water / pH 8 / Cooling with ice View Scheme

roxarsone (121-19-7) → 4-methoxy-3-nitrophenylarsonic acid (193970-71-7)

Conditions	Yield
bei der Methylierung;
bei der Methylierung;

roxarsone (121-19-7) → (3-bromo-4-hydroxy-5-nitro-phenyl)-arsonic acid

Conditions	Yield
With methanol; bromine; iron

roxarsone (121-19-7) → 3-amino-2-hydroxy-5-hydroxyarsinoyl-benzenesulfonic acid

Conditions	Yield
With sodium hydroxide; sodium dithionite unter Kuehlung;

roxarsone (121-19-7) → (4-hydroxy-3-nitro-phenyl)-phenyl-arsinic acid (875241-21-7)

Conditions	Yield
With hydrogenchloride; sulfur dioxide; potassium iodide anschliessend mit Benzoldiazoniumchlorid;

roxarsone (121-19-7) → (4-hydroxy-3,5-dinitro-phenyl)-arsonic acid (6269-50-7)

Conditions	Yield
With nitric acid

Upstream product

• 5430-08-0 (4-chloro-3-nitro-phenyl)-arsonic acid 
• 98-14-6 4-hydroxyphenylarsonic acid 
• 860602-62-6 (4-bromo-3-nitro-phenyl)-arsonic acid 
• 873985-38-7 (4-iodo-3-nitro-phenyl)-arsonic acid 
• 741258-62-8 (4-anilino-3-nitro-phenyl)-arsonic acid 
• 7664-93-9 sulfuric acid 
• 5440-06-2 (4-amino-3-nitro-phenyl)-arsonic acid 
• 5440-04-0 4-chlorobenzenearsonic acid 
• 618-22-4 arsacetin 
• 6324-92-1 p-iodophenylarsonic acid 
• 55048-80-1 (4-bromophenyl)arsonic acid 
• 108-95-2 phenol 
• 91484-30-9 (4-dimethylamino-phenyl)-arsonic acid 
• 861528-00-9 (4-dimethylamino-3-nitro-phenyl)-arsonic acid 

Downstream Products

• 21784-73-6 4-iodo-2-nitrophenol 
• 2163-77-1 3-amino-4-hydroxyphenylarsonic acid 
• 102107-61-9 4-Arsenoso-2-nitro-phenol 
• 193970-71-7 4-methoxy-3-nitrophenylarsonic acid 
• 875241-21-7 (4-hydroxy-3-nitro-phenyl)-phenyl-arsinic acid 
• 6269-50-7 (4-hydroxy-3,5-dinitro-phenyl)-arsonic acid 
• 873985-17-2 (4-benzyloxy-3-nitro-phenyl)-arsonic acid 
• 60956-29-8 (4-acetoxy-3-nitro-phenyl)-arsonic acid 

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Photocatalytic degradation of Roxarsone (cas 121-19-7) by using synthesized ZnO nanoplates09/24/2019

An efficient photodegradation of roxarsone (ROX) was achieved by using synthesized zinc oxide (ZnO) nanoplates under UV light irradiation. ZnO nanoplates were synthesized by facile wet chemical method. Characterization of ZnO nanoparticles was done by X-ray diffraction (XRD), Fourier transform i...detailed

Biotransformation of arsenic-containing Roxarsone (cas 121-19-7) by an aerobic soil bacterium Enterobacter sp. CZ-1☆09/10/2019

Roxarsone (3-nitro-4-hydroxyphenylarsonic acid, ROX) is an arsenic-containing compound widely used as a feed additive in poultry industries. ROX excreted in chicken manure can be transformed by microbes to different arsenic species in the environment. To date, most of the studies on microbial tr...detailed

Tumor-promoting and pro-angiogenic effects of Roxarsone (cas 121-19-7) via VEGFR2/PLCγ/PKC signaling09/09/2019

Roxarsone is an organoarsenic feed additive used in livestock and poultry production that is released into the environment, where it poses a risk to human health. It is known to have a tumor-promoting effect that is brought about by pro-angiogenic factors such as vascular endothelial growth fact...detailed

Effect of enrofloxacin and Roxarsone (cas 121-19-7) on CYP450s in pig09/08/2019

Enrofloxacin (ENR) and roxarsone (ROX) have been widely used in animal breeding. In this study, the daily clinical dosage of ENR and daily additive amount of ROX were administrated to Bama pigs. After 5 days, the activity and protein expression of three important enzymes in the cytochrome P450 f...detailed

Roxarsone (cas 121-19-7) exposure jeopardizes nitrogen removal and regulates bacterial community in biological sequential batch reactors09/07/2019

Roxarsone is widely present in wastewaters of many animal farms in China. However, little is known about how long-term roxarsone exposure influences the nitrogen removal of biological wastewater treatment in agricultural settings. Here we investigated the nitrogen removal performance of a biolog...detailed

Effect of Roxarsone (cas 121-19-7) metabolites in chicken manure on soil biological property09/06/2019

Roxarsone (ROX), an organoarsenic feed additive, occurs as itself and its metabolites including As(V), As(III), monomethylarsonic acid (MMA) and dimethylarsinic acid (DMA) in animal manure. Animal manure improves soil biological property, whereas As compounds impact microorganisms. The integral ...detailed

Transformation of Roxarsone (cas 121-19-7) during UV disinfection in the presence of ferric ions09/05/2019

The transformation of roxarsone (ROX) during UV disinfection with Fe(III) has been investigated. Fe(OH)2+, as the main Fe(III) species at pH = 3, produces HO under UV irradiation leading to the oxidation of ROX. Dissolved oxygen plays a very important role in the continuous conversion of generat...detailed

Effects of Roxarsone (cas 121-19-7) and sulfadiazine on biogas production and their degradation during anaerobic digestion09/04/2019

Roxarsone and sulfadiazine are typical feed additives and often occur in manure and livestock wastewater. Anaerobic digestion is a common technique for the treatment of manure and livestock wastewater. However, the influence of roxarsone and sulfadiazine on anaerobic digestion and their degradat...detailed

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