4-(2,4-Dichlorophenoxy)aniline

4-(2,4-Dichlorophenoxy)aniline
Identifiers
CAS Number	14861-17-7;
3D model (JSmol)	Interactive image;
ChemSpider	25088;
ECHA InfoCard	100.035.378
EC Number	238-932-7;
PubChem CID	26940;
UNII	R41F3KF27M;
CompTox Dashboard (EPA)	DTXSID3065825 ;
	InChI InChI=1S/C12H9Cl2NO/c13-8-1-6-12(11(14)7-8)16-10-4-2-9(15)3-5-10/h1-7H,15H2 Key: RWDOREOERSVIRK-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1N)OC2=C(C=C(C=C2)Cl)Cl;
Properties
Chemical formula	C12H9Cl2NO
Molar mass	254.11 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-(2,4-Dichlorophenoxy)aniline is a chemical compound belonging to the substance group of diphenyl ethers.

Representation and synthesis

4-(2,4-Dichlorophenoxy)aniline is obtained by catalytic reduction of nitrofen (nitrofen).^[1]

Occurrence

Approximately 15% of 4-(2,4-dichlorophenoxy)aniline is formed as a secondary degradation product during the metabolism of the herbicide nitrofen in rats via reduction of the nitro group. Further degradation occurs either to 4-(4-aminophenoxy)-2,5-dichlorophenol through ring hydroxylation or to 4-(2,4-dichlorophenoxy)acetanilide via acetylation.^[2]

Use

4-(2,4-Dichlorophenoxy)aniline serves as an intermediate in the production of the pesticide diclofop-methyl.^[3]^[1]

References

1 2 Jaana Koistinen (2000), "Polychlorinated Diphenyl Ethers (PCDE)", Volume 3 Anthropogenic Compounds Part K, The Handbook of Environmental Chemistry, vol. 3K, Berlin, Heidelberg: Springer, pp. 157–201, doi:10.1007/3-540-48915-0_7, ISBN 978-3-540-48915-3
↑ T. J. Brown, J. M. Manson (1986), "Further characterization of the distribution and metabolism of nitrofen in the pregnant rat", Teratology, vol. 34, no. 2, pp. 129–139, doi:10.1002/tera.1420340202, PMID 3775667
↑ Berufsgenossenschaft Rohstoffe und chemische Industrie, ed. (August 1993), "Aminofen" (PDF), Toxikologische Bewertungen (Nr. 232), Heidelberg

[JKoistinen-1] 1 2 Jaana Koistinen (2000), "Polychlorinated Diphenyl Ethers (PCDE)", Volume 3 Anthropogenic Compounds Part K, The Handbook of Environmental Chemistry, vol. 3K, Berlin, Heidelberg: Springer, pp. 157–201, doi:10.1007/3-540-48915-0_7, ISBN 978-3-540-48915-3

[2] T. J. Brown, J. M. Manson (1986), "Further characterization of the distribution and metabolism of nitrofen in the pregnant rat", Teratology, vol. 34, no. 2, pp. 129–139, doi:10.1002/tera.1420340202, PMID 3775667

[BGRCI-3] Berufsgenossenschaft Rohstoffe und chemische Industrie, ed. (August 1993), "Aminofen" (PDF), Toxikologische Bewertungen (Nr. 232), Heidelberg

[1]

[2]

[3]