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3,4-Dichloroaniline

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3,4-Dichloroaniline
Names
Other names 1-amino-3,4-dichlorobenzene
Identifiers
CAS Number
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.227 Edit this at Wikidata
EC Number
  • 202-448-4
Gmelin Reference 602350
KEGG
PubChem CID
UNII
UN number 3442 1590
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H5Cl2N/c7-5-2-1-4(9)3-6(5)8/h1-3H,9H2Key: SDYWXFYBZPNOFX-UHFFFAOYSA-N

    2.1.4 SMILES

    C1=CC(=C(C=C1N)Cl)Cl
Properties
Chemical formula C6H5Cl2N
Molar mass 162.01 g·mol
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 GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 , 100 kPa). Infobox references
Chemical compound

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.

Preparation

It is produced by hydrogenation of 3,4-dichloronitrobenzene.

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.

References

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