4-Hydroxy-3-nitrobenzenearsonic acid

4-Hydroxy-3-nitrobenzenearsonic acid
IUPAC name 4-Hydroxy-3-nitrobenzenearsonic acid[citation needed]
Systematic name (4-Hydroxy-3-nitrophenyl)arsonic acid[1]
Other names 3-Nitro-4-hydroxyphenyl arsonic acid[citation needed] 2-Nitrophenol-4-arsonic acid[citation needed]
Identifiers
CAS number	121-19-7 Y
PubChem	5104
ChemSpider	4925 Y
EC number	204-453-7
UN number	3465
KEGG	D05771 Y
MeSH	Roxarsone
ChEBI	CHEBI:35817 Y
RTECS number	CY5250000
Beilstein Reference	1976533
Gmelin Reference	1221211
Jmol-3D images	Image 1 Image 2
SMILES Oc1ccc(cc1-n(:o):o)[As](O)(O)=O OC1=CC=C(C=C1[N+]([O-])=O)[As](O)(O)=O
InChI InChI=1S/C6H6AsNO6/c9-6-2-1-4(7(10,11)12)3-5(6)8(13)14/h1-3,9H,(H2,10,11,12) Y Key: XMVJITFPVVRMHC-UHFFFAOYSA-N Y 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) Key: XMVJITFPVVRMHC-UHFFFAOYAF
Properties
Molecular formula	C6AsNH6O6
Molar mass	263.0365 g mol-1
Melting point	>300 °C
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H301, H331, H410
GHS precautionary statements	P261, P273, P301+310, P311, P501
EU classification	T N
R-phrases	R23/25, R50/53
S-phrases	S20/21, S28, S45, S60, S61
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

4-Hydroxy-3-nitrobenzenearsonic acid is an organic compound that is widely used agriculturally as a chicken-feed additive. The molecule is a derivative of phenylarsonic acid (C₆H₅As(O)(OH)₂). This organoarsenic compound, usually under the tradename Roxarsone, has attracted attention as a source of arsenic contamination of the food chain. Approximately 1 million kilograms of this compound were produced in 2006 in the US.^[2] This compound was first reported in a 1923 British patent which describes the nitration and diazotization of arsanilic acid.^[3] When blended with calcite powder, it is widely used to make feed premixes in the poultry industry and is usually available in 5%, 20% and 50% concentrations.

In June 2011, the FDA gave Pfizer 30 days to discontinue selling this product; the FDA's findings indicated elevated (but 'very low') levels of arsenic in the livers of chickens consuming the arsonic acid.^[4]

References

Further reading

• J. R. Garbarino, A. J. Bednar, D. W. Rutherford, R. S. Beyer, and R. L. Wershaw (2003). "Environmental Fate of Roxarsone in Poultry Litter. I. Degradation of Roxarsone during Composting". Environ. Sci. Technol. 37 (8): 1509–1514. doi:10.1021/es026219q+S0013-936X(02)06219-3. PMID 12731831. 
• Chiou P. W.-S.; Chen K.-L.; Yu B.; (1997). "Effects of roxarsone on performance, toxicity, tissue accumulation and residue of eggs and excreta in laying". Journal of the science of food and agriculture 74 (2): 229–236. doi:10.1002/(SICI)1097-0010(199706)74:2<229::AID-JSFA793>3.0.CO;2-F. 
• R. L. Wershaw, J. R. Garbarino, and M. R. Burkhardt. Roxarsone in Natural Water Systems. http://water.usgs.gov/owq/AFO/proceedings/afo/pdf/Wershaw.pdf. 
• KB Kerr, JR Narveson, FA Lux (1969). "Toxicity of an organic arsenical, 3-nitro-4-hydroxyphenylarsonic acid. Residues in chicken tissues". Journal of Agricultural and Food Chemistry 17 (6): 1400. doi:10.1021/jf60166a021. 

External links

• No Arsenic In Pardoned Turkeys, But It Might Be In Yours at NPR