4-Chloroaniline

4-Chloroaniline

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Names
IUPAC name 4-chloroaniline
Other names p-chloroaniline
Identifiers
CAS Number	106-47-8 Y
ChEBI	CHEBI:20331 N
ChEMBL	ChEMBL15888 N
ChemSpider	7524 Y
Jmol 3D model	Interactive image
KEGG	C14450 Y
PubChem	7812
InChI InChI=1S/C6H6ClN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 N Key: QSNSCYSYFYORTR-UHFFFAOYSA-N N
SMILES C1=CC(=CC=C1N)Cl
Properties
Chemical 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)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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.

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. Some benzodiazepine drugs use 4-chloroaniline in their manufacture.

4-Chloroaniline can be used to make dorastine (antihistamine) and lorcainide (antiarrhythmic).