4-Chloroaniline

4-Chloroaniline
Names
	Preferred IUPAC name 4-Chloroaniline[1]
	Systematic IUPAC name 4-Chlorobenzenamine[1]
	Other names p-Chloroaniline
Identifiers
CAS Number	106-47-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:20331 ;
ChEMBL	ChEMBL15888 ;
ChemSpider	7524 ;
ECHA InfoCard	100.003.093
KEGG	C14450 ;
PubChem CID	7812;
UNII	Z553SGH315 ;
CompTox Dashboard (EPA)	DTXSID9020295 ;
	InChI InChI=1S/C6H6ClN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 Key: QSNSCYSYFYORTR-UHFFFAOYSA-N ;
	SMILES C1=CC(=CC=C1N)Cl;
Properties
Chemical formula	ClC6H4NH2
Appearance	Pale yellow solid
Density	1.43 g/cm3
Melting point	72.5 °C (162.5 °F; 345.6 K)
Boiling point	232 °C (450 °F; 505 K)
Solubility in water	2.6 g/L at 20 °C[2]
Hazards
Main hazards	Very toxic, possible carcinogen. Absorbed through skin.[3]
Safety data sheet	External MSDS
Flash point	113 °C (235 °F; 386 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

4-Chloroaniline is an organochlorine compound with the formula ClC₆H₄NH₂. This pale yellow solid is one of the three isomers of chloroaniline.

Preparation

4-Chloroaniline is not prepared from aniline, which tends to overchlorinate. Instead, it is prepared by reduction of 4-nitrochlorobenzene, which in turn is prepared by nitration of chlorobenzene.[4]

Uses

4-Chloroaniline is used in the industrial production of pesticides, drugs, and dyestuffs. It is a precursor to the widely used antimicrobial and bacteriocide chlorhexidine and is used in the manufacture of pesticides, including pyraclostrobin, anilofos, monolinuron, and chlorphthalim.[5] 4-Chloroaniline can be also used in the manufacture of some benzodiazepine drugs as well as the antihistamine dorastine, the antiarhythmic lorcainide, and the antifungal ontianil.

4-Chloroaniline can exhibit antimicrobial action against some bacteria and molds.[4]

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References

Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 669. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
Scheunert, 1981
"Safety data for 4-chloroaniline". Oxford University. Archived from the original on 2012-04-23. Retrieved 2008-03-11.
Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
Ashford’s Dictionary of Industrial Chemicals (3rd ed.). 2011. p. 1998.

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[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 669. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[2] Scheunert, 1981

[3] "Safety data for 4-chloroaniline". Oxford University. Archived from the original on 2012-04-23. Retrieved 2008-03-11.

[Booth-4] Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.

[5] Ashford’s Dictionary of Industrial Chemicals (3rd ed.). 2011. p. 1998.