4-Chloroaniline

4-Chloroaniline
IUPAC name 4-chloroaniline
Other names p-chloroaniline
Identifiers
CAS number	106-47-8 Y
PubChem	7812
ChemSpider	7524 Y
KEGG	C14450 Y
ChEMBL	CHEMBL15888 N
Jmol-3D images	Image 1
SMILES C1=CC(=CC=C1N)Cl
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, 346 K, 163 °F
Boiling point	232 °C, 505 K, 450 °F
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: Y/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