4-Chloroaniline

4-Chloroaniline
4-Chloroaniline
IUPAC name
4-chloroaniline
Other names
p-chloroaniline
Identifiers
CAS number 106-47-8 YesY
PubChem 7812
ChemSpider 7524 YesY
KEGG C14450 YesY
ChEMBL CHEMBL15888 N
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
Boiling point

232 °C
Solubility in water Negligible
Hazards
MSDS External MSDS
Main hazards Very toxic, possible carcinogen. Absorbed through skin.[1]
Flash point 113 °C
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

4-Chloroaniline is a 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

  1. ^ "Safety data for 4-chloroaniline". Oxford University. http://physchem.ox.ac.uk/MSDS/CH/4-chloroaniline.html. 
  2. ^ Gerald Booth (2007). "Nitro Compounds, Aromatic". In: Ullmann's Encyclopedia of Industrial Chemistry# John Wiley & Sons: New York# doi:10#1002/14356007#a17_411
  3. ^ Ashford’s Dictionary of Industrial Chemicals, 3rd edition, 2011, page 1998
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