4-Chloroaniline

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

4-Chloroaniline
Names
Preferred IUPAC name
4-Chloroaniline[1]
Systematic IUPAC name
4-Chlorobenzenamine[1]
Other names
p-Chloroaniline
Identifiers
3D model (JSmol)
471359
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.093
KEGG
RTECS number
  • BX0700000
UNII
UN number 2018
Properties
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)
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
H301, H311, H317, H331, H350, H400, H410
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

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
  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.
  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.
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