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;
Beilstein Reference	471359
ChEBI	CHEBI:20331 ;
ChEMBL	ChEMBL15888 ;
ChemSpider	7524 ;
ECHA InfoCard	100.003.093
KEGG	C14450 ;
PubChem CID	7812;
RTECS number	BX0700000;
UNII	Z553SGH315 ;
UN number	2018
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
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H317, H331, H350, H400, H410
GHS precautionary statements	P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+310, P302+352, P304+340, P308+313, P311, P312, P321, P322, P330, P333+313, P361, P363, P391, P403+233, P405
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]

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.