3,4-Dichloroaniline

3,4-Dichloroaniline
Names
	Other names 1-amino-3,4-dichlorobenzene
Identifiers
CAS Number	95-76-1 ;
ChEBI	CHEBI:16767;
ChEMBL	ChEMBL1319813;
ChemSpider	13860720;
ECHA InfoCard	100.002.227
EC Number	202-448-4;
Gmelin Reference	602350
KEGG	C02791;
PubChem CID	7257;
UNII	20KR9WJ4NS;
UN number	3442 1590
CompTox Dashboard (EPA)	DTXSID7021815 ;
	InChI InChI=1S/C6H5Cl2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2 Key: SDYWXFYBZPNOFX-UHFFFAOYSA-N 2.1.4 SMILES C1=CC(=C(C=C1N)Cl)Cl;
Properties
Chemical formula	C6H5Cl2N
Molar mass	162.01 g·mol−1
Density	1.57
Melting point	66–71 °C (151–160 °F; 339–344 K)
Boiling point	272 °C (522 °F; 545 K)
Solubility in water	92 mg/l at 20 °C
log P	2.69
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H317, H318, H331, H410
Precautionary statements	P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P321, P330, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	3 1 0
Flash point	166 °C (331 °F; 439 K)
Autoignition; temperature	269 °C (516 °F; 542 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3,4-Dichloroaniline is an organic compound with the formula C₆H₃Cl₂(NH₂). It is one of several isomers of dichloroaniline. It is a white solid although commercial samples often appear gray. It is a precursor to dyes, agricultural chemicals, and drugs including the antimalarial chlorproguanil and the herbicides propanil, linuron, DCMU, and diuron.^{[citation needed]}

Preparation

It is produced by hydrogenation of 3,4-dichloronitrobenzene.^[2]

Safety and environmental aspects

Being a precursor to some herbicides, the toxicity and fate of dichloroaniline is of interest. One pathway for the biodegradation of dichloroaniline is oxidation to the catechol derivatives.^[3]

References

^ "3,4-Dichloroaniline". pubchem.ncbi.nlm.nih.gov.
^ P. F. Vogt; J. J. Gerulis (2005). "Amines, Aromatic". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_037. ISBN 9783527303854.
^ Crossland, N.O. (1990). "A review of the fate and toxicity of 3,4-dichloroaniline in aquatic environments". Chemosphere. 21 (12): 1489–1497. Bibcode:1990Chmsp..21.1489C. doi:10.1016/0045-6535(90)90054-w.

[1] "3,4-Dichloroaniline". pubchem.ncbi.nlm.nih.gov.

[Ullmann-2] P. F. Vogt; J. J. Gerulis (2005). "Amines, Aromatic". Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_037. ISBN 9783527303854.

[3] Crossland, N.O. (1990). "A review of the fate and toxicity of 3,4-dichloroaniline in aquatic environments". Chemosphere. 21 (12): 1489–1497. Bibcode:1990Chmsp..21.1489C. doi:10.1016/0045-6535(90)90054-w.

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