tolidine

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 446718238

| Name = 2-Tolidine

| Reference = {{GESTIS|Name=ortho-Tolidin|ZVG=17950|CAS=119-93-7|Date=6.6.2008}}

| ImageFile = 2-tolidine.svg

| ImageAlt =

| PIN = 3,3′-Dimethyl-[1,1′-biphenyl]-4,4′-diamine

| OtherNames = o-Tolidine; Orthotolidine; Diaminoditolyl; Diaminotolyl; Bianisidine; Tolidine blue; 3,3'-Dimethylbenzidine; 4,4'-Bi-o-toluidine

|Section1={{Chembox Identifiers

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

| CASNo = 119-93-7

| ChEMBL = 85109

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

| UNII = 63HLO2IV6K

| PubChem = 8413

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

| KEGG = C14443

| SMILES = CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N)C)N

| InChI = 1/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3

| InChIKey = NUIURNJTPRWVAP-UHFFFAOYAK

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

| StdInChI = 1S/C14H16N2/c1-9-7-11(3-5-13(9)15)12-4-6-14(16)10(2)8-12/h3-8H,15-16H2,1-2H3

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

| StdInChIKey = NUIURNJTPRWVAP-UHFFFAOYSA-N

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

| ChEBI = 34320

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

| ChemSpiderID = 8106

| EINECS = 204-358-0

}}

|Section2={{Chembox Properties

| C=14 | H=16 | N=2

| Appearance = White to reddish crystals or powder

| Density = 1.23 g/cm³

| MeltingPtC = 129

| BoilingPtC = 300.5

| Solubility = 1.3 g/L}}

|Section3={{Chembox Hazards

| MainHazards = potential carcinogen

| FlashPtC = 244

| AutoignitionPtC =

| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|350|411}}

| PPhrases = {{P-phrases|201|202|264|270|273|281|301+312|308+313|330|391|405|501}}

| IDLH = Ca [N.D.]

| PEL = Handle with care

| REL = Ca C 0.02 mg/m³ [60-minute] [skin]

}}

}}

2-Tolidine (orthotolidine, o-tolidine; not to be confused with o-toluidine) is an organic compound with the chemical formula {{chem2|(C6H4(CH3)NH2)2}}. Several isomers are known; the 3-tolidine derivative is also important commercially. It is a colorless compound although commercial samples are often colored. It is slightly soluble in water. It forms salts with acids, such as the hydrochloride, which is commercially available.

2-Tolidine can be produced by benzidine rearrangement from a hydrazone derivative of 2-nitrotoluene.Noller, Carl R.: Textbook of Organic Chemistry, Springer Verlag, 1960{{verify source|reason=This book appears to not have been published in 1960, only 1958 and 1966, and with no page number it's impossible to identify what is being discussed here.|date=March 2025}}{{page needed|date=March 2025}}

:{{chem2|(CH3C6H4)2N2H2 -> (C6H3(CH3)NH2)2}}