| Revision as of 17:28, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 476626617 of page 2-Nitroaniline for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'ChEMBL', 'StdInChI', 'StdInChIKey'). |
Latest revision as of 07:26, 14 December 2024 edit Octaazacubane (talk | contribs)158 editsm Fixed a typo in the density unit |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 393563665 |
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| verifiedrevid = 477214789 |
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| Name = 2-Nitroaniline |
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| Name = 2-Nitroaniline |
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| ImageFile = 2-nitroaniline chemical structure.png |
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| ImageFileL1 = 2-nitroaniline chemical structure.png |
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| ImageSize = 150px |
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| ImageSizeL1 = 130 |
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| ImageAltL1 = Skeletal formula of 2-nitroaniline |
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| ImageName = 2-Nitroaniline |
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| ImageFileR1 = 2-Nitroaniline-3D-balls.png |
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| IUPACName = 2-nitroaniline |
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| ImageSizeR1 = 130 |
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| OtherNames = ''ortho''-nitroaniline, ''o''-nitroaniline, 2-nitrobenzenamine |
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| ImageAltR1 = Ball-and-stick model of the 2-nitroaniline molecule |
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| Section1 = {{Chembox Identifiers |
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| ImageName = 2-Nitroaniline |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| PIN = 2-Nitroaniline |
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| SystematicName = 2-Nitrobenzenamine |
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| OtherNames = ''ortho''-Nitroaniline<br />''o''-Nitroaniline |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 88-74-4 |
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| CASNo = 88-74-4 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 274009 --> |
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| ChEMBL = 274009 |
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| ChemSpiderID = 6680 |
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| ChemSpiderID = 13853943 |
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| PubChem = 6946 |
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| SMILES = O=()c1ccccc1N |
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| EC_number = 201-855-4 |
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| InChI = 1/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 |
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| RTECS = BY6650000 |
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| InChIKey = DPJCXCZTLWNFOH-UHFFFAOYAV |
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| UNNumber = 1661 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| UNII = 2519U0541L |
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| StdInChI = <!-- blanked - oldvalue: 1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 --> |
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| SMILES = O=()c1ccccc1N |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| InChI = 1/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 |
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| StdInChIKey = <!-- blanked - oldvalue: DPJCXCZTLWNFOH-UHFFFAOYSA-N --> |
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| InChIKey = DPJCXCZTLWNFOH-UHFFFAOYAV |
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| RTECS = |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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| StdInChI = 1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 |
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| Section2 = {{Chembox Properties |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| Formula = C<sub>6</sub>H<sub>6</sub>N<sub>2</sub>O<sub>2</sub> |
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| StdInChIKey = DPJCXCZTLWNFOH-UHFFFAOYSA-N |
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| MolarMass = 138.14 g/mol |
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}} |
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| Appearance = Orange Solid |
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|Section2={{Chembox Properties |
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| Density = |
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| C=6 | H=6 | N=2 | O=2 |
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| Solubility = 0.117 g/100 ml (20°C) (SIDS) |
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| Appearance = Orange solid |
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| pKb = |
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| Density = 1.442 g/ml |
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}} |
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| MeltingPtC = 71.5 |
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| Section3 = {{Chembox Structure |
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| BoilingPtC = 284 |
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| CrystalStruct = ?<!-- e.g. ], ], ], ], ], ], ], and mention "close packed" or similar. You may also cite what class it belongs to, e.g. ] --> |
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| Solubility = 0.117 g/100 ml (20°C) (SIDS) |
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| Dipole = |
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| pKa = -0.3 (of anilinium salt) |
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}} |
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| MagSus = -66.47·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section7 = {{Chembox Hazards |
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}} |
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| MainHazards = |
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|Section7={{Chembox Hazards |
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| FlashPt = |
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| GHSPictograms = {{GHS06}}{{GHS08}} |
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| RPhrases = |
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| SPhrases = |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|311|331|373|412}} |
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}} |
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| 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}} |
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| Section8 = {{Chembox Related |
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| FlashPtC = 168 |
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| OtherCpds = ], ] |
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}} |
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}} |
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|Section8={{Chembox Related |
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| OtherCompounds = ], ] |
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}} |
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}} |
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'''2-Nitroaniline''' is an ] with the formula H<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub>. It is a derivative of ], carrying a ] ] in position 2.<ref>{{cite web |url=http://msds.chem.ox.ac.uk/NI/o-nitroaniline.html |title=Safety data for o-nitroaniline |access-date=2011-01-17 |archive-date=2009-06-28 |archive-url=https://web.archive.org/web/20090628152854/http://msds.chem.ox.ac.uk/NI/o-nitroaniline.html |url-status=dead }}</ref> It is mainly used as a precursor to o-phenylenediamine. |
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==Synthesis== |
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2-Nitroaniline is prepared commercially by the reaction of ] with ]:<ref name=Booth/> |
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:ClC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + 2 NH<sub>3</sub> → H<sub>2</sub>NC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + NH<sub>4</sub>Cl |
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Many other methods exist for the synthesis of this compound. Direct nitration of aniline is inefficient since anilinium is produced instead. Nitration of acetanilide gives only traces of 2-nitro isomer is obtained due to the great steric effect of the amide. Sulfonation is usually used to block the 4 position and increases the effectiveness to 56%.<ref>{{cite book|title=Organic chemistry|last1=T. W. Grahan|first1=Solomons|last2=Craig|first2=B. Fryhle|last3=Scott|first3=A. Snyder|year=2011|isbn=978-1119077251|edition= 11|pages= 606–607|publisher=John Wiley & Sons }}</ref><ref>{{cite journal |author=Louis Ehrenfeld, Milton Puterbaugh|doi=10.15227/orgsyn.009.0064|title=o-Nitrianiline|journal=Organic Syntheses|year=1929|volume=9|page=64}}</ref> |
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] |
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==Uses and reactions== |
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2-Nitroaniline is the main precursor to ]s, which are converted to ]s, a family of ]s that are key components in pharmaceuticals.<ref name=Booth>{{Ullmann|author=Gerald Booth|title=Nitro Compounds, Aromatic|year=2007|doi=10.1002/14356007.a17_411}}</ref> |
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] |
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Aside from its reduction to phenylenediamine, 2-nitroaniline undergoes other reactions anticipated for aromatic amines. It is protonated to give the anilinium salts. Owing to the influence of the nitro substituent, the amine exhibits a basicity nearly 100,000x lower than aniline itself. Diazotization gives ],<ref>{{cite journal|title=1,2,3-Benzothiadiazole 1,1-Dioxide|author1=G. Wittig |author2=R. W. Hoffmann|journal=Org. Synth.|year=1967|volume=47|page=4|doi=10.15227/orgsyn.047.0004}}</ref> which is a precursor to some ]s. Acetylation affords 2-nitroacetanilide. |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{Reflist}} |
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==External links== |
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* {{Webarchive|url=https://web.archive.org/web/20140808035151/http://faculty.ycp.edu/~jforesma/educ/pchem/stojowski/ona.htm |date=2014-08-08 }} |
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{{DEFAULTSORT:Nitroaniline, 2-}} |
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] |
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] |