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.

References

{{reflist}}

{{DEFAULTSORT:Nitroaniline, 3-}}

Category:Anilines

Category:Nitrobenzene derivatives