4-Chloroaniline

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4-Chloroaniline
4-Chloranilin.svg
Names
IUPAC name
4-chloroaniline
Other names
p-chloroaniline
Identifiers
106-47-8 YesY
ChEBI CHEBI:20331 N
ChEMBL ChEMBL15888 N
ChemSpider 7524 YesY
Jmol-3D images Image
KEGG C14450 YesY
PubChem 7812
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
SDS External MSDS
Main hazards Very toxic, possible carcinogen. Absorbed through skin.[1]
Flash point 113 °C (235 °F; 386 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

4-Chloroaniline is an organochlorine compound with the formula ClC6H4NH2. This pale yellow solid is one of several known chloroanilines.

Preparation[edit]

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[edit]

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[edit]

  1. ^ "Safety data for 4-chloroaniline". Oxford University. 
  2. ^ Booth, G. (2005), "Nitro Compounds, Aromatic", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a17_411 
  3. ^ Ashford’s Dictionary of Industrial Chemicals, 3rd Edition, 2011, page 1998