4-Chloroaniline
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| Names | |
|---|---|
| Preferred IUPAC name
4-Chloroaniline[1] | |
| Systematic IUPAC name
4-Chlorobenzenamine[1] | |
| Other names
p-Chloroaniline
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.003.093 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Very toxic, possible carcinogen. Absorbed through skin.[3] |
| Flash point | 113 °C (235 °F; 386 K) |
| Safety data sheet (SDS) | External MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 hydrogenation 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.[citation needed]
4-Chloroaniline is has antimicrobial action against some bacteria and molds.[4]
References
- ^ a b 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 [full citation needed]
- ^ "Safety data for 4-chloroaniline". Oxford University.
- ^ a b Gerald Booth (2007). "Nitro Compounds, Aromatic". Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.
{{cite journal}}: Cite journal requires|journal=(help); Unknown parameter|encyclopedia=ignored (help) - ^ Ashford’s Dictionary of Industrial Chemicals (3rd ed.). 2011. p. 1998.