3-Nitroaniline
{{chembox
| Watchedfields = changed
| verifiedrevid = 477219834
| Name = 3-Nitroaniline
| ImageFileL1 = 3-nitroaniline chemical structure.png
| ImageSizeL1 = 130px
| ImageAltL1 = Skeletal formula of 3-nitroaniline
| ImageFileR1 = 3-Nitroaniline-3D-balls.png
| ImageSizeR1 = 130
| ImageAltR1 = Ball-and-stick model of the 3-nitroaniline molecule
| PIN = 3-Nitroaniline
| SystematicName = 3-Nitrobenzenamine
| OtherNames = meta-Nitroaniline
m-Nitroaniline
|Section1={{Chembox Identifiers
| SMILES = O=[N+]([O-])c1cccc(N)c1
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7145
| InChI = 1/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2
| InChIKey = XJCVRTZCHMZPBD-UHFFFAOYAY
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 14068
| PubChem = 7423
| EC_number = 202-729-1
| RTECS = BY6825000
| UNNumber = 1661
| UNII = CM50SM561T
| DTXSID = DTXSID6025725
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XJCVRTZCHMZPBD-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 99-09-2
}}
|Section2={{Chembox Properties
| C=6 | H=6 | N=2 | O=2
| Appearance = Yellow solid
| Density = 0.9011
| Solubility = 0.1 g/100 ml (20 °C)
| MeltingPtC = 114
| MeltingPt_notes =
| BoilingPtC = 306
| BoilingPt_notes =
| pKa = 2.47
| pKb =
| MagSus = −70.09·10−6 cm3/mol
}}
|Section3={{Chembox Structure
| CrystalStruct =
| Dipole =
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| MainHazards =
| FlashPtC =
| GHSPictograms = {{GHS06}}{{GHS08}}
| GHSSignalWord = Danger
| 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}}
}}
|Section8={{Chembox Related
| OtherCompounds = 2-Nitroaniline, 4-Nitroaniline
}}
}}
3-Nitroaniline is an organic compound with the formula H2NC6H4NO2. A yellow solid, it is a derivative of aniline, carrying a nitro functional group in position 3. It is an isomer of 2-nitroaniline and 4-nitroaniline. It is used as a precursor to dyes.{{Ullmann|author=Gerald Booth|title=Nitro Compounds, Aromatic|year=2007|doi=10.1002/14356007.a17_411}}
Synthesis and applications
File:DisperseYellow5.svg derived from 3-nitroaniline.|left]]
3-Nitroaniline is produced on a commercial scale by reduction of 1,3-dinitrobenzene with hydrogen sulfide, or sodium sulfide (a Zinin reaction).
It is used as a chemical intermediate for azo coupling component and the dyes disperse yellow 5 and acid blue 29.