Nitrofen

Nitrofen
Names
	Preferred IUPAC name 2,4-Dichloro-1-(4-nitrophenoxy)benzene
	Other names Nitrophen; Nitrofene; 2,4-Dichlorophenyl 4-nitrophenyl ether
Identifiers
CAS Number	1836-75-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	15010;
ECHA InfoCard	100.015.824
PubChem CID	15787;
UNII	N71UYG034A ;
CompTox Dashboard (EPA)	DTXSID7020970 ;
	InChI InChI=1S/C12H7Cl2NO3/c13-8-1-6-12(11(14)7-8)18-10-4-2-9(3-5-10)15(16)17/h1-7H Key: XITQUSLLOSKDTB-UHFFFAOYSA-N; InChI=1/C12H7Cl2NO3/c13-8-1-6-12(11(14)7-8)18-10-4-2-9(3-5-10)15(16)17/h1-7H Key: XITQUSLLOSKDTB-UHFFFAOYAU;
	SMILES Clc2cc(Cl)ccc2Oc1ccc([N+]([O-])=O)cc1;
Properties
Chemical formula	C12H7Cl2NO3
Molar mass	284.09 g·mol−1
Appearance	Colorless, crystalline solid
Density	1.80 g/cm3 at 83 °C
Melting point	64–71 °C (147–160 °F; 337–344 K) (technical)
Solubility in water	0.7-1.2 mg/L at 22 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Nitrofen is an herbicide of the diphenyl ether class. Because of concerns about its carcinogenicity, the use of nitrofen has been banned in the European Union^[2] and in the United States since 1996.^[1]^[3] It has been superseded by related protoporphyrinogen oxidase enzyme inhibitors including acifluorfen and fomesafen.

In 2002, Nitrofen was detected in organic feed, organic eggs, and organic poultry products in Germany prompting a scandal which caused a decline in all organic meat sales in Europe.^[4]^[5]

Nitrofen is listed as an IARC Group 2B carcinogen, meaning it is "possibly carcinogenic to humans".^[6]

References

^ ^a ^b Nitrofen data sheet, INCHEM WHO/FAO report, March 1999.
^ Banned pesticide in German grain, Pesticides News No. 57, September 2002, page 22
^ Pesticide Properties Database. "Nitrofen". University of Hertfordshire. Retrieved 2021-03-03.
^ Nitrofen scandal causes organic meat sales to dip, Just Food, October 2, 2002.
^ Organic scandal halts Germany's green revolution, by John Hooper, The Guardian, June 12, 2002.
^ IARC Monographs - Classifications - by Group

External links

Nitrofen in the Pesticide Properties DataBase (PPDB)

[inchem-1] Nitrofen data sheet, INCHEM WHO/FAO report, March 1999.

[2] Banned pesticide in German grain, Pesticides News No. 57, September 2002, page 22

[PPDB-3] Pesticide Properties Database. "Nitrofen". University of Hertfordshire. Retrieved 2021-03-03.

[4] Nitrofen scandal causes organic meat sales to dip, Just Food, October 2, 2002.

[5] Organic scandal halts Germany's green revolution, by John Hooper, The Guardian, June 12, 2002.

[6] IARC Monographs - Classifications - by Group

[1]