3,5-Dichloroaniline

3,5-Dichloroaniline
Names
	Other names 1-amino-3,5- dichlorobenzene
Identifiers
CAS Number	626-43-7;
3D model (JSmol)	Interactive image;
Beilstein Reference	636492
ChEBI	CHEBI:19904;
ChEMBL	ChEMBL1451208;
ChemSpider	11778;
ECHA InfoCard	100.009.954
EC Number	210-948-9;
Gmelin Reference	363409
PubChem CID	12281;
UNII	OZ75ZM1S3G;
CompTox Dashboard (EPA)	DTXSID7030307 ;
	InChI InChI=1S/C6H5Cl2N/c7-4-1-5(8)3-6(9)2-4/h1-3H,9H2 Key: UQRLKWGPEVNVHT-UHFFFAOYSA-N;
	SMILES C1=C(C=C(C=C1Cl)Cl)N;
Properties
Chemical formula	C6H5Cl2N
Molar mass	162.01 g·mol−1
Appearance	colorless solid
Density	1.58 g/cm3
Melting point	51–53 °C (124–127 °F; 324–326 K)
Boiling point	260 °C (500 °F; 533 K) 741 torr
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331, H373, H410
Precautionary statements	P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3,5-Dichloroaniline is an organic compound with the formula C₆H₃Cl₂(NH₂). It is one of several isomers of dichloroaniline. It is a colorless solid although commercial samples often appear colored. It is produced by hydrogenation of 3,5-dichloronitrobenzene.^[2] It is a precursor to the fungicide vinclozolin.

Safety and environmental aspects

Its 72-h EC₅₀ in an algal growth inhibition assay is 4.39 mg/L.^[3] Biodegradation of dichloroanilines usually proceeds via initial ring hydroxylation.^[4]

References

^ "3,5-Dichloroaniline". pubchem.ncbi.nlm.nih.gov.
^ Jagadeesh, Rajenahally V.; Surkus, Annette-Enrica; Junge, Henrik; Pohl, Marga-Martina; Radnik, Jörg; Rabeah, Jabor; Huan, Heming; Schünemann, Volker; Brückner, Angelika; Beller, Matthias (2013). "Nanoscale Fe₂O₃-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines". Science. 342 (6162): 1073–1076. Bibcode:2013Sci...342.1073J. doi:10.1126/science.1242005. PMID 24288327.
^ Aruoja, Villem; Sihtmäe, Mariliis; Dubourguier, Henri-Charles; Kahru, Anne (2011). "Toxicity of 58 substituted anilines and phenols to algae Pseudokirchneriella subcapitata and bacteria Vibrio fischeri: Comparison with published data and QSARs". Chemosphere. 84 (10): 1310–1320. Bibcode:2011Chmsp..84.1310A. doi:10.1016/j.chemosphere.2011.05.023. PMID 21664645.
^ Suchana, Shamsunnahar; Araujo, Sofia Pimentel; Lomheim, Line; Mack, E. Erin; Spain, Jim C.; Edwards, Elizabeth; Passeport, Elodie (2024). "Compound-Specific Carbon, Nitrogen, and Hydrogen Isotope Analysis to Characterize Aerobic Biodegradation of 2,3-Dichloroaniline by a Mixed Enrichment Culture". Environmental Science & Technology. 58 (27): 12042–12050. Bibcode:2024EnST...5812042S. doi:10.1021/acs.est.4c02173. PMID 38934904.

[1] "3,5-Dichloroaniline". pubchem.ncbi.nlm.nih.gov.

[2] Jagadeesh, Rajenahally V.; Surkus, Annette-Enrica; Junge, Henrik; Pohl, Marga-Martina; Radnik, Jörg; Rabeah, Jabor; Huan, Heming; Schünemann, Volker; Brückner, Angelika; Beller, Matthias (2013). "Nanoscale Fe₂O₃-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines". Science. 342 (6162): 1073–1076. Bibcode:2013Sci...342.1073J. doi:10.1126/science.1242005. PMID 24288327.

[3] Aruoja, Villem; Sihtmäe, Mariliis; Dubourguier, Henri-Charles; Kahru, Anne (2011). "Toxicity of 58 substituted anilines and phenols to algae Pseudokirchneriella subcapitata and bacteria Vibrio fischeri: Comparison with published data and QSARs". Chemosphere. 84 (10): 1310–1320. Bibcode:2011Chmsp..84.1310A. doi:10.1016/j.chemosphere.2011.05.023. PMID 21664645.

[4] Suchana, Shamsunnahar; Araujo, Sofia Pimentel; Lomheim, Line; Mack, E. Erin; Spain, Jim C.; Edwards, Elizabeth; Passeport, Elodie (2024). "Compound-Specific Carbon, Nitrogen, and Hydrogen Isotope Analysis to Characterize Aerobic Biodegradation of 2,3-Dichloroaniline by a Mixed Enrichment Culture". Environmental Science & Technology. 58 (27): 12042–12050. Bibcode:2024EnST...5812042S. doi:10.1021/acs.est.4c02173. PMID 38934904.

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