4-Chloroaniline
| 4-Chloroaniline | |
|---|---|
 | |
| 4-chloroaniline | |
| Other names p-chloroaniline | |
| Identifiers | |
| CAS number | 106-47-8  |
| PubChem | 7812 |
| ChemSpider | 7524 |
| KEGG | C14450 |
| ChEMBL | CHEMBL15888  |
| Jmol-3D images | Image 1 |
| |
| Properties | |
| Molecular formula | 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 |
| Solubility in water | 2.6 g/litre at 20 °C (Scheunert, 1981) |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Very toxic, possible carcinogen. Absorbed through skin.[1] |
| Flash point | 113 °C; 235 °F; 386 K |
| (verify) (what is: /?) Except where noted otherwise, 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 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.[2]
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.[3] Some benzodiazepine drugs use 4-chloroaniline in their manufacture.
References
- ↑ "Safety data for 4-chloroaniline". Oxford University.
- ↑ Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry, John Wiley & Sons: New York, doi:10.1002/14356007.a17_411
- ↑ Ashford’s Dictionary of Industrial Chemicals, 3rd Edition, 2011, page 1998