:4-Chloroaniline
{{short description|Chemical compound}}
{{chembox
| Section8 = {{Chembox Related
| OtherCompounds = 2,4,6-Trichloroaniline
}}
| ImageFile = 4-Chloranilin.svg
| ImageSize = 80px
| PIN = 4-Chloroaniline{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 669 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}
| SystematicName = 4-Chlorobenzenamine
| OtherNames = p-Chloroaniline
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 13869339
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=106-47-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z553SGH315
| PubChem=7812
| Beilstein = 471359
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 20331
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 15888
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14450
| RTECS = BX0700000
| UNNumber = 2018
| SMILES=C1=CC(=CC=C1N)Cl
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H6ClN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QSNSCYSYFYORTR-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| Formula=ClC6H4NH2
| Appearance=Pale yellow solid
| Density=1.43 g/cm3
| MeltingPtC=72.5
| BoilingPtC=232
| Solubility= 2.6 g/L at 20 °CScheunert, 1981 {{full|date=January 2018}}
}}
| Section3 = {{Chembox Hazards
| ExternalSDS = [http://physchem.ox.ac.uk/MSDS/CH/4-chloroaniline.html External MSDS]
| MainHazards= Very toxic, possible carcinogen. Absorbed through skin.{{cite web | publisher = Oxford University | url = http://physchem.ox.ac.uk/MSDS/CH/4-chloroaniline.html | title = Safety data for 4-chloroaniline | access-date = 2008-03-11 | archive-url = https://web.archive.org/web/20120423084727/http://physchem.ox.ac.uk/msds/CH/4-chloroaniline.html | archive-date = 2012-04-23 | url-status = dead }}
| FlashPtC = 113
| AutoignitionPtC =
| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|301|311|317|331|350|400}}
| PPhrases = {{P-phrases|201|202|261|264|270|271|272|273|280|281|301+310|302+352|304+340|308+313|311|312|321|322|330|333+313|361|363|391|403+233|405|501}}
}}
}}
4-Chloroaniline is an organochlorine compound with the formula ClC6H4NH2. This pale yellow solid is one of the three isomers of chloroaniline.
Preparation
4-Chloroaniline is not prepared from aniline, which tends to overchlorinate. Instead, it is prepared by reduction of 4-nitrochlorobenzene, which in turn is prepared by nitration of chlorobenzene.{{cite encyclopedia|author=Gerald Booth|title=Nitro Compounds, Aromatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2007|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_411|isbn=9783527303854 }}
Uses
4-Chloroaniline is used in the industrial 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.{{cite book | title = Ashford's Dictionary of Industrial Chemicals | edition = 3rd | date = 2011 | pages = 1998}}
4-Chloroaniline exhibits antimicrobial action against some bacteria and molds.