Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and 4-Nitroaniline: Difference between pages

| verifiedrevid = 477223057

| Name = 4-Nitroaniline

| ImageFileL1 = p-Nitroanilin.svg

| ImageSizeL1 = 65px

| ImageAltL1 = Skeletal formula of p-nitroaniline

| ImageFileR1 = 4-Nitroaniline-3D-balls.png

| ImageSizeR1 = 110

| ImageAltR1 = Ball-and-stick model of the p-nitroaniline molecule

| ImageFile3 = P-nitroanilin.jpg

| ImageSize3 =

| PIN = 4-Nitroaniline

| SystematicName = 4-Nitrobenzenamine

| OtherNames = ''p''-Nitroaniline<br />1-Amino-4-nitrobenzene<br />''p''-Nitrophenylamine

|Section1={{Chembox Identifiers

| PubChem = 7475

| EC_number = 202-810-1

| RTECS = BY7000000

| UNNumber = 1661

| KEGG = C02126

| Gmelin = 27331

| Beilstein = 508690

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 13846959

| SMILES = c1cc(ccc1N)N(=O)=O

| InChI = 1/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2

| InChIKey = TYMLOMAKGOJONV-UHFFFAOYAW

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = TYMLOMAKGOJONV-UHFFFAOYSA-N

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 17064

| ChEMBL = 14282

}}

|Section2={{Chembox Properties

| Formula = C₆H₆N₂O₂

| MolarMass = 138.12 g/mol

| Appearance = yellow or brown powder

| Odor = faint, ammonia-like

| Density = 1.437 g/ml, solid

| Solubility = 0.8 mg/ml at 18.5 °C (IPCS)

| MeltingPtC = 146 to 149

| MeltingPt_notes = (lit.)

| BoilingPtC = 332

| BoilingPt_notes =

| VaporPressure = 0.00002 mmHg (20°C)<ref name=PGCH/>

| MagSus = -66.43·10⁻⁶ cm³/mol

}}

|Section7={{Chembox Hazards

| ExternalSDS = [http://hazard.com/msds/mf/baker/baker/files/n4170.htm JT Baker]

| MainHazards = Toxic

| NFPA-H = 2

| NFPA-F = 1

| NFPA-R = 0

| NFPA-S =

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

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|301|311|331|373|412}}

| PPhrases = {{P-phrases|260|261|264|270|271|273|280|301+310|302+352|304+340|311|312|314|321|322|330|361|363|403+233|405|501}}

| FlashPtC = 199

| PEL = TWA 6 mg/m3 (1 ppm) [skin]<ref name="PGCH">{{PGCH|0449}}</ref>

| IDLH = 300 mg/m³<ref name=PGCH/>

| REL = TWA 3 mg/m³ [skin]<ref name=PGCH/>

| LD50 = 3249 mg/kg (rat, oral)<br/>750 mg/kg (rat, oral)<br/>450 mg/kg (guinea pig, oral)<br/>810 mg/kg (mouse, oral)<ref>{{IDLH|100016|p-Nitroaniline}}</ref>

}}

|Section8={{Chembox Related

| OtherCompounds = [[2-Nitroaniline]], [[3-Nitroaniline]]

}}

'''4-Nitroaniline''', '''p-nitroaniline''' or '''1-amino-4-nitrobenzene''' is an [[organic compound]] with the formula C₆H₆N₂O₂. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor.<ref name=Ullmann/>

==Synthesis==

4-Nitroaniline is produced industrially via the amination of [[4-Nitrochlorobenzene|4-nitrochlorobenzene]]:<ref name="Ullmann">{{Cite book |last=Booth |first=Gerald |url=https://onlinelibrary.wiley.com/doi/book/10.1002/14356007 |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2003-03-11 |publisher=Wiley |isbn=978-3-527-30385-4 |editor-last=Wiley-VCH |edition=1 |language=en |chapter=Nitro Compounds, Aromatic |doi=10.1002/14356007.a17_411 |chapter-url=https://onlinelibrary.wiley.com/doi/abs/10.1002/14356007.a17_411}}]</ref>

:ClC₆H₄NO₂ + 2 NH₃ → H₂NC₆H₄NO₂ + NH₄Cl

Below is a laboratory synthesis of 4-nitroaniline from [[aniline]]. The key step in this reaction sequence is an [[electrophilic aromatic substitution]] to install the nitro group ''para'' to the amino group. The amino group can be easily protonated and become a meta director. Therefore, a protection of the acetyl group is required. After this reaction, a separation must be performed to remove 2-nitroaniline, which is also formed in a small amount during the reaction.<ref>{{Cite book |last1=Mohrig |first1=J.R. |title=Experimental Organic Chemistry |last2=Morrill |first2=T.C. |last3=Hammond |first3=C.N. |last4=Neckers |first4=D.C. |publisher=Freeman |year=1997 |location=New York, NY |pages=456–467 |chapter=Synthesis 5: Synthesis of the Dye Para Red from Aniline |access-date=2007-07-18 |chapter-url=http://web.centre.edu/muzyka/organic/lab/paraRed05.htm |archive-url=https://web.archive.org/web/20200915092617/http://web.centre.edu/muzyka/organic/lab/paraRed05.htm |archive-date=2020-09-15 |url-status=dead}}</ref><br />

[[File:Synthesis of nitroaniline.svg|600px|]]

==Applications==

4-Nitroaniline is mainly consumed industrially as a precursor to [[P-Phenylenediamine|''p''-phenylenediamine]], an important dye component. The reduction is effected using iron metal and by catalytic hydrogenation.<ref name=Ullmann/>

It is a starting material for the synthesis of [[Para Red]], the first [[azo dye]]:<ref>{{Cite book |last=Williamson |first=Kenneth L. |url=https://archive.org/details/macroscalemicros00will_0 |title=Macroscale and Microscale Organic Experiments, Fourth Edition |publisher=[[Houghton-Mifflin]] |year=2002 |isbn=0-618-19702-8 |url-access=registration}}</ref>

[[File:Synthesis Para Red.svg|700px|center|Synthesis of Para Red]]

It is also a precursor to [[2,6-Dichloro-4-nitroaniline|2,6-dichloro-4-nitroaniline]], also used in dyes.

===Laboratory use===

Nitroaniline undergoes [[diazotization]], which allows access to [[1,4-Dinitrobenzene|1,4-dinitrobenzene]]<ref>{{Cite journal |last=Starkey |first=E. B. |year=1939 |title=p-DINITROBENZENE |url=http://orgsyn.org/demo.aspx?prep=CV2P0225 |journal=Organic Syntheses |volume=19 |page=40 |doi=10.15227/orgsyn.019.0040}}</ref> and nitrophenylarsonic acid.<ref>{{Cite journal |year=1946 |title=p-Nitrophenylarsonic Acid |url=http://orgsyn.org/demo.aspx?prep=CV3P0665 |journal=Organic Syntheses |volume=26 |page=60 |doi=10.15227/orgsyn.026.0060|first1=A. Wayne |last1=Ruddy |first2= Edgar B. |last2=Starkey

}}</ref> With phosgene, it converts to 4-nitrophenyl[[isocyanate]].<ref>{{Cite journal |last1=Shriner |first1=R. L. |last2=Horne |first2=W. H. |last3=Cox |first3=R. F. B. |year=1934 |title=p-NITROPHENYL ISOCYANATE |url=http://orgsyn.org/demo.aspx?prep=CV2P0453 |journal=Organic Syntheses |volume=14 |page=72 |doi=10.15227/orgsyn.014.0072}}</ref>

<ref>{{Cite journal |year=1932 |title=2,6-Diiodo-p-Nitroaniline |journal=Organic Syntheses |volume=12 |page=28 |doi=10.15227/orgsyn.012.0028|first1=R. B. |last1=Sandin|first2=W. V. |last2=Drake |last3=Leger|first3=Frank }}</ref>

===Carbon snake demonstration===

When heated with sulfuric acid, it dehydrates and polymerizes explosively into a rigid foam.<ref>{{Cite journal |last1=Poshkus |first1=A. C. |last2=Parker |first2=J. A. |year=1970 |title=Studies on nitroaniline–sulfuric acid compositions: Aphrogenic pyrostats |url=https://onlinelibrary.wiley.com/doi/10.1002/app.1970.070140813 |journal=Journal of Applied Polymer Science |volume=14 |issue=8 |pages=2049–2064 |doi=10.1002/app.1970.070140813}}</ref>

In [[Carbon snake]] demo, paranitroaniline can be used instead of sugar, if the experiment is allowed to proceed under an obligatory [[fumehood]].<ref>{{Cite book |last1=Summerlin |first1=Lee R. |url=https://eric.ed.gov/?id=ED286722 |title=Chemical Demonstrations: A Sourcebook for Teachers Volume 1 |last2=Ealy |first2=James L. |publisher=[[American Chemical Society]] |year=1988 |isbn=978-0-841-21481-1 |edition=2nd |pages=171 |chapter=Experiment 100: Dehydration of p-Nitroaniline: Sanke and Puff}}</ref> With this method the reaction phase prior to the black snake's appearance is longer, but once complete, the black snake itself rises from the container very rapidly.<ref>{{Cite web |date=2013-06-06 |title=Carbon Snake: demonstrating the dehydration power of concentrated sulfuric acid |url=https://communities.acs.org/t5/Educators-and-Students/Carbon-Snake-demonstrating-the-dehydration-power-of-concentrated/td-p/7732 |access-date=2022-01-31 |website=communities.acs.org |language=en}}</ref> This reaction may cause an [[explosion]] if too much sulfuric acid is used.<ref>{{Citation |title=Making a carbon snake with P-Nitroaniline | date=7 April 2014 |url=https://www.youtube.com/watch?v=YKHUnHDphTc |access-date=2022-01-31 |language=en}}</ref>

==Toxicity==

The compound is toxic by way of inhalation, ingestion, and absorption, and should be handled with care. Its {{LD50}} in rats is 750.0&nbsp;mg/kg when administered orally. 4-Nitroaniline is particularly harmful to all aquatic organisms, and can cause long-term damage to the environment if released as a pollutant.<ref>{{Cite web |date=December 18, 2020 |title=4-Nitroaniline |url=https://www.sigmaaldrich.com/SG/en/sds/aldrich/185310 |publisher=Sigma-Aldrich |location=St. Louis, Missouri}}</ref>

==See also==

*[[2-Nitroaniline]]

*[[3-Nitroaniline]]

==References==

<references/>

==External links==

{{commons category}}

*[https://web.archive.org/web/20071011164242/http://ptcl.chem.ox.ac.uk/MSDS/NI/p-nitroaniline.html Safety (MSDS)data for p-nitroaniline]

*[http://hazard.com/msds/mf/baker/baker/files/n4170.htm MSDS Sheet for ''p-''nitroaniline]

*[http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/185310 Sigma-Aldrich Catalog data]

*[https://www.cdc.gov/niosh/npg/npgd0449.html CDC - NIOSH Pocket Guide to Chemical Hazards]

{{DEFAULTSORT:Nitroaniline, 4-}}

[[Category:Anilines]]

[[Category:Dyes]]

[[Category:Hazardous air pollutants]]

[[Category:IARC Group 3 carcinogens]]

[[Category:Nitrobenzene derivatives]]

[[Category:Corrosion inhibitors]]