Roxarsone
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Roxarsone
structure -
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CAS No:
121-19-7
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Formula:
C6H6AsNO6
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Chemical Name:
Roxarsone
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Synonyms:
Arsonic acid,As-(4-hydroxy-3-nitrophenyl)-;Benzenearsonic acid,4-hydroxy-3-nitro-;Arsonic acid,(4-hydroxy-3-nitrophenyl)-;As-(4-Hydroxy-3-nitrophenyl)arsonic acid;Aklomix-3;4-Hydroxy-3-nitrobenzenearsonic acid;4-Hydroxy-3-nitrophenylarsonic acid;2-Nitro-1-hydroxybenzene-4-arsonic acid;3-Nitro-4-hydroxybenzenearsonic acid;3-Nitro-4-hydroxyphenylarsonic acid;Ristat;Roxarsone;Ren-O-sal;3-Nitro-10;3-Nitro-20;3-Nitro-50;3-Nitro-80;3-Nitro;p-Hydroxy-m-nitrophenylarsonic acid;NSC 2101;8028-23-7;8028-22-6
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CAS No:
Description
BEIGE-BROWN FINE CRYSTALLINE POWDERChEBI: An organoarsonic acid where the organyl group is 4-hydroxy-3-nitrophenyl.Pale yellow crystals or light tan powder.
4-hydroxy-3-nitrophenyl arsonic acid appears as pale yellow crystals or light tan powder. (NTP, 1992)|Solid
4-hydroxy-3-nitrophenyl arsonic acid appears as pale yellow crystals or light tan powder. (NTP, 1992)|Roxarsone is an organoarsonic acid where the organyl group is 4-hydroxy-3-nitrophenyl. It has a role as a coccidiostat, an antibacterial drug, an agrochemical and an animal growth promotant. It is an organoarsonic acid and a member of 2-nitrophenols. It derives from a phenylarsonic acid.|Roxarsone is an organoarsenic molecule added to poultry feed. The addition of this compound to poultry feed improves weight gain and feed efficiency as well as prevent the growth of coccidian parasites. The drug is also approved in the United States for use in pigs.|An arsenic derivative which has anticoccidial action and promotes growth in animals.
Roxarsone Basic Attributes
263.04
263.04
204-453-7
H5GU9YQL7L
757312|2101
1557
DTXSID9020956
Tufts of pale-yellow needles or rhombohedral plates from water|Pale-yellow crystals
29319090
Characteristics
124
-0.51
4-hydroxy-3-nitrophenyl arsonic acid appears as pale yellow crystals or light tan powder. (NTP, 1992)
2.02 g/cm3
≥300 °C(lit.)
537.3±60.0 °C(Predicted)
240.3±21.3 °C
H2O: <0.1 g/100 mL at 23 ºC;Slightly sol in cold water; freely sol in methanol, ethanol, acetic acid, acetone, alkalies; sol in about 30 parts boiling water; insol in ether, ethyl acetate; sparingly sol in dil mineral acids.
0-6°C
2.24E-12mmHg at 25°C
Oral-rat LDL0: 82 mg/kg; Oral-Mouse LD50: 244 mg/kg
Thermal decomposition of toxic nitrogen oxides and arsenide gases
145.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Puffs up and deflagrates on heating
Insoluble in water.
Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
May be sensitive to light and elevated temperatures on long-term storage. It puffs up and deflagrates on heating. Incompatible with strong oxidizers and strong acids. Forms mono-, di-, and trisodium salts. (NTP, 1992)
Safety Information
III
6.1(b)
UN 3465 6.1/PG 2
3
23/25-50/53
20/21-28-45-60-61
CY5250000
T,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Stable under normal shipping and handling conditions.
P261-P273-P301 + P310-P311-P501
H301 + H331-H410
Roxarsone tablets. ... Conditions of use: growing chickens and growing turkeys ... Indications for use: For increased rate of weight gain, improved feed efficiency, and improved pigmentation. ... Conditions of use: swine ... Indication for use: As an aid in the treatment of swine dysentery (hemorrhagic enteritis or bloody scours).
DHHS/ATSDR; Toxicological Profile for Arsenic (Update) TP-92/02 (1993)|DHHS/NTP; Toxicology & Carcinogenesis Studies of Roxarsone in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 345 (1989) NIH Publication No. 89-2800
Flash point data are not available for this chemical; however, it is probably combustible. (NTP, 1992)
|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P301+P310, P304+P340, P311, P321, P330, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 92 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this material may be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this material from exposure to light, and store it in a refrigerator. (NTP, 1992)
MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Permissible Exposure Limit: Table Z-1 8-Hr Time Weighted Avg: 0.5 mg/cu m. /Arsenic, organic cmpd (as As)/
Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 3-Nitro-4-hydroxyphenylarsonic acid is included on this list.|(a) The owner or operator of an existing glass melting furnace subject to the provisions of this subpart shall comply with either paragraph (a)(1) or (a)(2) of this section ... (1) Uncontrolled total arsenic emissions from the glass melting furnace shall be less than 2.5 Mg (2.7 ton) per year, or ... (2) Total arsenic emissions from glass melting furnace shall be conveyed to a control device and reduced by at least 85%. /Total arsenic/|(b) The owner or operator of a new or modified glass melting furnace subject to the provisions of this subpart shall comply with either paragraph (b)(1) or (b)(2) of this section ... (1) Uncontrolled total arsenic emissions from the glass melting furnace shall be less than 0.4 Mg (0.44 ton) per year, or ... (2) Total arsenic emissions from glass melting furnace shall be conveyed to a control device and reduced by at least 85%. /Total arsenic/|The owner or operator of each copper converter subject to the provisions of this subpart shall reduce inorganic arsenic emissions to the atmosphere by meeting the following design, equipment, work practice, and operational requirements: (1) Install, operate, and maintain a secondary hood system on each copper converter. Each secondary hood system shall consist of a hood enclosure, air curtain fan(s), exhaust system fan(s), and ductwork that conveys the captured emission to a control device ... (2) Optimize the capture of secondary inorganic arsenic emission by operating the copper converter and secondary hood systems at all times ... . /Inorganic arsenic/
D004; A waste containing arsenic may or may not be characterized as a hazardous waste following testing by the Toxicity Characteristic Leaching Procedure as prescribed by the Resource Conservation and Recovery Act (RCRA) regulations. /Arsenic/
Toxicity
highly toxic
LD50 Rat oral 81 mg/kg|LD50 Mouse oral 244 mg/kg|LD50 Chicken oral 110 mg/kg|LD50 Chicken ip 34 mg/kg|For more Non-Human Toxicity Values (Complete) data for 3-NITRO-4-HYDROXYPHENYLARSONIC ACID (8 total), please visit the HSDB record page.
... Toxicology and carcinogenesis studies were conducted by admin roxarsone (greater than 99.4% pure) in feed to groups of F344/N rats and B6C3F1 mice of each sex for ... 2 years. ... Dietary concn of roxarsone selected for the 2 yr studies were 0, 50, or 100 ppm for rats and 0, 100, or 200 ppm for mice. Conclusions: Under the conditions of these 2 yr feed studies, there was equivocal evidence of carcinogenic activity of roxarsone for male F344/N rats, as indicated by a marginally incr incidence of adenomas of the exocrine pancreas. There was no evidence of carcinogenic activity for female F344/N rats fed diets containing 50 or 100 ppm roxarsone for 2 yr. There was no evidence of carcinogenic activity for male or female B6C3F1 mice fed diets containing 100 or 200 ppm roxarsone for 2 yr.
Drug Information
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals. (See all compounds classified as Coccidiostats.)
WHEN GIVEN ORALLY, CONSIDERABLE PERCENTAGE IS EXCRETED IN FECES, INDICATING THAT PHENYLARSONIC COMPD ARE POORLY ABSORBED BY INTESTINAL TRACT. THAT PROP WHICH IS ABSORBED, HOWEVER IS APPARENTLY EXCRETED RAPIDLY BY THE KIDNEYS.|4-WK-OLD CHICKENS FED DAILY RATION WITH 50 PPM ROXARSONE & SACRIFICIED. PPM ARSENIC IN CONTROLS: KIDNEY 0.05, LIVER 0.08, MUSCLE 0.02, SKIN 0.02; ARSENIC IN TREATED ANIMALS KILLED ON 70TH DAY: KIDNEY 0.64, LIVER 1.26, MUSCLE 0.04, SKIN 0.05.|IT IS ESTABLISHED THAT ARSANILIC ACID & ACETYLARSONIC ACID ARE EXCRETED UNCHANGED BY CHICKENS. SIMILAR RESULTS WERE OBTAINED IN STUDIES WITH 3-NITRO-4-HYDROXYBENZENEARSONIC ACID IN CHICKENS.|There are only a few reports on the excretion of arsenic in the milk of animals. The arsenic level in cow's milk did not incr with the blood concn when the cows were fed methylarsonic acid or dimethylarsinic acid... . However, the milk arsenic levels did incr when cows were fed arsanilic acid or 3-nitro-4-hydroxyphenylarsonic acid (1.6-3.2 mg As/kg bw)... .
SYMPTOMS: This compound may cause irritation. Symptoms of exposure to this class of compounds include restlessness, nausea, vomiting, headache, dizziness, chills, cramps, irritability and variable paralysis that may progress over a period of several weeks. Ventricular arrhythmias may occur. Inhalation of dusts may cause acute pulmonary edema, restlessness, dyspnea, cyanosis, cough with foamy sputum, and rales. The principle manifestations are gastrointestinal disturbances. Chronic poisoning can result in polyneuritis, optic neuritis, anesthesias, paresthesias, bronzing of the skin, alopecia, localized edema, dermatitis, liver cirrhosis, abdominal pain, salivation, anemia, weight loss, chronic nephritis, cardiac failure and dependent edema. Ingestion of lethal doses of this type of compound can cause violent gastroenteritis, convulsions and coma. Death may occur from circulatory failure. ACUTE/CHRONIC HAZARDS: This compound is highly toxic by ingestion. It may be fatal by inhalation or skin absorption. When heated to decomposition it emits very toxic fumes of carbon monoxide and carbon dioxide. It also emits toxic fumes of nitrogen oxides and arsenic oxides. (NTP, 1992)
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: Some heavy metals are VERY TOXIC POISONS, especially if their salts are very soluble in water (e.g., lead, chromium, mercury, bismuth, osmium, and arsenic). IMMEDIATELY call a hospital or poison control center and locate activated charcoal, egg whites, or milk in case the medical advisor recommends administering one of them. Also locate Ipecac syrup or a glass of salt water in case the medical advisor recommends inducing vomiting. Usually, this is NOT RECOMMENDED outside of a physician's care. If advice from a physician is not readily available and the victim is conscious and not convulsing, give the victim a glass of activated charcoal slurry in water or, if this is not available, a glass of milk, or beaten egg whites and IMMEDIATELY transport victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, assure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)
3 Nitro 10
Roxarsone Use and Manufacturing
There are many synthetic routes of Roxasane, mainly including: ① It is obtained by digesting p-hydroxyphenylarsinic acid as a raw material through mixed acid at low temperature; ② 3-Nitro-4-hydroxyaniline is diazotized and replaced (arsine) Obtained; ③ obtained by arsenication and nitration using phenol as raw material; ④ p-aminophenylarsonic acid is obtained by substitution of diazotization to obtain hydroxyphenylarsonic acid, which is then nitrated; ⑤ using p-hydroxyaniline as raw material by diazotization, Prepared by arsine and nitrification. Judging from the source of raw materials, the cost, the length of the route, the yield, and the ease of operation, routes ③ and ⑤ have advantages and are suitable for industrial production. The reaction formula and steps of the synthesis ⑤ are as follows: 109.5 p-aminophenol and 135.5 g of industrial hydrochloric acid are added to the reactor and stirred at room temperature to make it fully salted. Cool to 0℃, dropwise add 30% sodium nitrite solution to generate diazonium salt solution. The control temperature should not exceed 5℃. Check the diazotization end point with starch-KI test paper. 98.9g of A2O3 and 30% sodium carbonate solution were heated and stirred in the reactor to completely dissolve and boiled for 0.5 hours. Cool to 10°C, add a few drops of CuSO4 solution, and slowly add the diazonium salt solution to this sodium arsenite solution containing copper hydrochloride to react to form a solution of sodium parahydroxyarsine, controlling the temperature not to exceed 10°C. Acidified with dilute hydrochloric acid, filtered, the filtrate was neutralized to neutrality, concentrated in vacuo, then added a small amount of activated carbon to decolorize, filtered while hot, the filtrate was left overnight, crystals were precipitated, and the crude product was filtered. The crude product was dissolved in water, acidified with dilute hydrochloric acid, cooled to 10°C, and left to recrystallize overnight. After filtration and drying, 171.8 g of p-hydroxyarsinic acid was obtained, melting point 172-174°C (decomposition), yield 78.1%. Stir 110g of p-hydroxyphenylarsinic acid in 397mL sulfuric acid. After cooling to 0℃, add 150.9g of mixed acid (23% sulfuric acid, 44% nitric acid, the rest is water), control the temperature not to exceed 18℃, and maintain 20℃ after addition Reaction 2h. The reaction was poured into ice water, filtered and washed to neutrality, the crude product was added with deionized aqueous solution, a small amount of activated carbon was added for heating to decolorize, and filtered while hot. The filtrate was left for 2 days, crystals were precipitated, filtered and vacuum dried to obtain 102.9g of product, melting point 300-302 ℃, yield 78.2%. In addition, it can also be synthesized using chloroaniline as a raw material. About dissolving 12.8g (0.1mol) of p-chloroaniline in 60mL water and 18mL concentrated hydrochloric acid solution, slowly adding a solution of 6.9g (0.1mol) sodium nitrite and 25mL water at 0-5°C. After the dropwise addition, keep warm and add 1.5g of cuprous chloride and silicone defoamer 1Ml, then slowly add 19.8g (0.1mol) of 2 arsenic trioxide and 8g (0.2mol of sodium hydroxide dissolved in 100mL of water) After the dropwise addition, 10 mL of 10% sodium hydroxide solution was added, and the reaction was continued for 1 h, then the temperature was raised to 60° C. for 1 h. Suction filtration, the filtrate was added with concentrated hydrochloric acid to adjust PH=4, and then suction filtration was performed, and the filtrate was concentrated to about 80 mL , Add activated carbon to decolorize and filter. The filtrate is added with concentrated hydrochloric acid to adjust PH=2, put in the refrigerator overnight, collect the precipitate, wash with water and dry to obtain 20.4g of yellowish crystal p-chloroarsinic acid, yield 86.3%, melting point greater than 270℃. Sodium nitrate 12.5g (0.15mol) was dissolved in 60mL concentrated sulfuric acid, 23.6g (0.1mol) of p-chlorophenylarsinic acid was slowly added dropwise with stirring. The temperature was raised to 80-85°C and the reaction was completed after 2h. Cool to room temperature, slowly Slowly pour into a mixture of 100g of ice and 100mL of water. Filter, wash with water, and dry to obtain 24.5g of 4-chloro-3-nitrophenylarsinic acid as pale yellow crystals, yield 87.2%, melting point greater than 270°C. Sodium hydroxide 15.0 g (0.375mol) was dissolved in 35mL water, then added 4-chloro-3-nitrophenylarsinic acid 14.1g (0.05mol), the reaction was stirred at 95-100 ℃ for 10h. Then add 30mL water, adjust the pH with concentrated hydrochloric acid =10, add activated carbon to decolorize and filter at 80°C. The filtrate is added with concentrated hydrochloric acid to adjust PH=2, and put it in the refrigerator overnight. After filtration, washing and drying, 9.4g of yellow crystals are obtained, melting point is greater than 270°C, and the yield is 71.5%.
Formerly in manufacture of arsphenamines; as reagent for zirconium.
(1977) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS
Arsonic acid, As-(4-hydroxy-3-nitrophenyl)-: ACTIVE|FORMS MONO-, DI-, & TRISODIUM SALTS.|APPLICATIONS (VET): DO NOT ADMIN TO DUCKS, GEESE, LAYING HENS, OR DOGS. ... ITS SAFE USE DEMANDS ADEQUATE WATER INTAKE & NO OTHER SOURCES OF ARSENIC. INCOORDINATION, RICKETS-LIKE APPEARANCE, & PARALYSIS CAN OCCUR UNDER THESE CONDITIONS.|APPLICATIONS (VET): FOR MANY YEARS IT HAD BEEN OTC FAVORITE FOR WATER MEDICATION OF CECAL COCCIDIOSIS IN CHICKS. OF VALUE IN IMPROVING PIGMENTATION IN CHICKENS & TURKEYS.|IS RECOMMENDED @ 25-50 PPM FOR CHICKENS & TURKEYS & @ 25-75 PPM FOR SWINE FOR IMPROVING WT GAIN & FEED EFFICIENCY. IT IS ALSO RECOMMENDED @ LEVEL OF 200 PPM FOR 5 DAYS FOR CONTROL OF SWINE DYSENTERY.
SPECTROPHOTOMETRY IN FEEDS; ANALYTICAL CHEMISTRY IN FEEDS.
Computed Properties
Molecular Weight:263.04
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:1
Exact Mass:262.941106
Monoisotopic Mass:262.941106
Topological Polar Surface Area:124
Heavy Atom Count:14
Complexity:270
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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