4-Fluoronitrobenzene

{{Chembox

| ImageFile = 4-Fluornitrobenzol.svg

| ImageSize = 110

| ImageAlt =

| IUPACName =

| OtherNames = 1-fluoro-4-nitrobenzene, 1-nitro-4-fluorobenzene

|Section1={{Chembox Identifiers

| CASNo = 350-46-9

| CASNo_Ref = {{Cascite|correct|CAS}}

| ChEMBL = 163729

| ChemSpiderID = 13856885

| EINECS = 206-502-8

| PubChem = 9590

| UNII = A2M2FH7XHH

| StdInChI=1S/C6H4FNO2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H

| StdInChIKey = WFQDTOYDVUWQMS-UHFFFAOYSA-N

| SMILES = C1=CC(=CC=C1[N+](=O)[O-])F

}}

|Section2={{Chembox Properties

| C = 6|H=4|F=1|O=2|N=1

| MolarMass =

| Appearance = yellow solid, melting near room temperature

| Density = 1.340 g/cm³

| MeltingPtC = 22-24

| MeltingPt_notes =

| BoilingPtC = 206

| BoilingPt_notes =

| Solubility = }}

|Section3={{Chembox Hazards

| GHS_ref={{cite web |title=1-Fluoro-4-nitrobenzene |url=https://pubchem.ncbi.nlm.nih.gov/compound/9590#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |language=en}}

| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301|302|312|317|331|373|412}}

| PPhrases = {{P-phrases|260|261|264|270|271|272|273|280|301+316|301+317|302+352|304+340|316|317|319|321|330|333+313|362+364|403+233|405|501}}

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

4-Fluoronitrobenzene is an organic compound with the formula FC₆H₄NO₂. It is one of three isomeric fluoronitrobenzenes.Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. {{doi|10.1002/14356007.a17_411}} A yellow oil, it is prepared from 4-nitrochlorobenzene using the Halex process:

:{{chem2|O2NC6H4Cl + KF -> O2NC6H4F + KCl}}

4-Fluoronitrobenzene can be hydrogenated to give 4-fluoroaniline,{{cite journal |doi=10.1126/science.1242005 |title=Nanoscale Fe₂O₃-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines |year=2013 |last1=Jagadeesh |first1=Rajenahally V. |last2=Surkus |first2=Annette-Enrica |last3=Junge |first3=Henrik |last4=Pohl |first4=Marga-Martina |last5=Radnik |first5=Jörg |last6=Rabeah |first6=Jabor |last7=Huan |first7=Heming |last8=Schünemann |first8=Volker |last9=Brückner |first9=Angelika |last10=Beller |first10=Matthias |journal=Science |volume=342 |issue=6162 |pages=1073–1076 |pmid=24288327 |bibcode=2013Sci...342.1073J |s2cid=11780985 }} which is a precursor to the fungicide {{ill|fluoroimide|de}} and parafluorofentanyl.

Owing to the presence of the electron withdrawing nitro group, the fluoride is a good leaving group in fluoronitrobenzenes. Thus reaction with phenoxide gives the mononitrodiphenylether.{{cite journal |doi=10.15227/orgsyn.014.0066 |title=p-Nitrodiphenyl Ether |journal=Organic Syntheses |year=1934 |volume=14 |page=66|first1=Ray Q.|last1=Brewster|first2=Theodore |last2=Groening }}