4-Chloroaniline
 | |
| Names | |
|---|---|
| Preferred IUPAC name
4-Chloroaniline[1] | |
| Systematic IUPAC name
4-Chlorobenzenamine[1] | |
| Other names
p-Chloroaniline | |
| Identifiers | |
106-47-8  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:20331  |
| ChEMBL | ChEMBL15888 |
| ChemSpider | 7524 |
| ECHA InfoCard | 100.003.093 |
| KEGG | C14450 |
| PubChem | 7812 |
| UNII | Z553SGH315 |
| |
| |
| Properties | |
| C6H6ClN | |
| Molar mass | 127.57154 g/mol |
| Appearance | pale yellow solid |
| Density | 1.43 g·cm−3 |
| Melting point | 72.5 °C (162.5 °F; 345.6 K) |
| Boiling point | 232 °C (450 °F; 505 K) |
| 2.6 g/litre at 20 °C (Scheunert, 1981) | |
| Hazards | |
| Main hazards | Very toxic, possible carcinogen. Absorbed through skin.[2] |
| 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). | |
| verify (what is ?) | |
| Infobox references | |
4-Chloroaniline is an organochlorine compound with the formula ClC6H4NH2. This pale yellow solid is one of several known chloroanilines.
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.[3]
Uses
4-Chloroaniline is an important building block used in the chemical industry for the 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.[4] Some benzodiazepine drugs use 4-chloroaniline in their manufacture.
4-Chloroaniline can be used to make dorastine (antihistamine) and lorcainide (antiarrhythmic).
References
- 1 2 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.
- ↑ "Safety data for 4-chloroaniline". Oxford University.
- ↑ Booth, G. (2005), "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 Edition, 2011, page 1998