Aniline Yellow

{{chembox

| Watchedfields = changed

| verifiedrevid = 457130888

| ImageFile = Aminoazobenzene.svg

| ImageSize = 220

| ImageName = Skeletal formula

| ImageFile1 = Aniline-yellow-3D-balls.png

| ImageSize1 = 220

| ImageName1 = Ball-and-stick model

| PIN = 4-(Phenyldiazenyl)aniline

| OtherNames = para-Aminoazobenzene
4-Phenylazoaniline
AAB
Brasilazina oil Yellow G
Ceres Yellow
Fast spirit Yellow
Induline R
Oil Yellow AAB
Oil Yellow AN
Oil Yellow B
Oil Yellow 2G
Oil Yellow R
Organol Yellow
Organol Yellow 2A
Solvent Yellow
Somalia Yellow 2G
Stearix Brown 4R
Sudan Yellow R
Sudan Yellow RA
C.I. 11000

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 5828

| InChI = 1/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2/b15-14+

| InChIKey = QPQKUYVSJWQSDY-CCEZHUSRBB

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C12H11N3/c13-10-6-8-12(9-7-10)15-14-11-4-2-1-3-5-11/h1-9H,13H2/b15-14+

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = QPQKUYVSJWQSDY-CCEZHUSRSA-N

| CASNo = 60-09-3

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 57X2AH42T1

| EINECS = 200-453-6

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 83761

| PubChem = 6051

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C19187

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

| ChEBI = 233869

| SMILES = N(=N/c1ccc(N)cc1)\c2ccccc2

}}

|Section2={{Chembox Properties

| Formula = C₆H₅N=NC₆H₄NH₂ (C₁₂H₁₁N₃)

| MolarMass = 197.24 g/mol

| Appearance =

| MeltingPtC = 123 to 126

| MeltingPt_notes =

| BoilingPt= >

| BoilingPtC = 360

| Solubility =

| Density = 1.19 g/mL

| pKa = 2.82 (25 ºC)

| MagSus = −118.3·10⁻⁶ cm³/mol

}}

|Section3={{Chembox Hazards

| MainHazards = Highly toxic
Suspected carcinogen

| NFPA-H = 0

| NFPA-F = 2

| NFPA-R = 1

| GHSPictograms = {{GHS08}}{{GHS09}}

| FlashPt =

| AutoignitionPt =

| LD50 = 200 mg/kg (mouse)

| GHSSignalWord = Danger

}}

}}

Aniline Yellow is a yellow azo dye and an aromatic amine. It is a derivative of azobenzene. It has the appearance of an orange powder.

Aniline Yellow was the first azo dye. it was first produced in 1861 by C. Mene. The second azo dye was Bismarck Brown in 1863. Aniline Yellow was commercialized in 1864 as the first commercial azo dye, a year after aniline black. It is manufactured from aniline.