4-Chloroaniline

4-Chloroaniline

Names
Preferred IUPAC name 4-Chloroaniline [1]
Other names p-Chloroaniline
Identifiers
CAS Number	106-47-8  Y
3D model (JSmol)	Interactive image
Beilstein Reference	471359
ChEBI	CHEBI:20331  Y
ChEMBL	ChEMBL15888  Y
ChemSpider	13869339  Y
ECHA InfoCard	100.003.093
KEGG	C14450  Y
PubChem CID	7812
RTECS number	BX0700000
UNII	Z553SGH315  Y
UN number	2018
CompTox Dashboard (EPA)	DTXSID9020295
InChI InChI=1S/C6H6ClN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 Y Key: QSNSCYSYFYORTR-UHFFFAOYSA-N Y
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
Occupational safety and health (OHS/OSH):
Main hazards	Very toxic, possible carcinogen. Absorbed through skin. [3]
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H317, H331, H350, H400
Precautionary statements	P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P312, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, P501
Flash point	113 °C (235 °F; 386 K)
Safety data sheet (SDS)	External MSDS
Related compounds
Related compounds	2,4,6-Trichloroaniline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). 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 exhibits antimicrobial action against some bacteria and molds. ^[4]

References

1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. P-62.2.1.1.1. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
2. Scheunert, 1981 ^{[ full citation needed ]}
3. "Safety data for 4-chloroaniline". Oxford University. Archived from the original on 2012-04-23. Retrieved 2008-03-11.
4. Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN   9783527303854.
5. Ashford's Dictionary of Industrial Chemicals (3rd ed.). 2011. p. 1998.