indoline
{{chembox
| Watchedfields = changed
| verifiedrevid = 443873282
| Name = Indoline
| ImageFile = Indoline numbering.svg
| ImageName = Indoline
| ImageFile1 = Indoline3d.png
| ImageName1 = Indoline
| PIN = 2,3-Dihydro-1H-indole
| OtherNames = 2,3-Dihydroindole
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9905
| InChI = 1/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 43295
| SMILES = c1cccc2c1CCN2
| InChIKey = LPAGFVYQRIESJQ-UHFFFAOYAF
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 388803
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = LPAGFVYQRIESJQ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 496-15-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6DPT9AB2NK
| PubChem = 10328
| RTECS = NL6906300
| Beilstein = 111915
}}
|Section2={{Chembox Properties
| Appearance = Clear colourless liquid
| Formula = C8H9N
| MolarMass = 119.16 g/mol
| Density = 1.063 g/mL
| MeltingPtC = -21
| BoilingPtC = 220 to 221
| BoilingPt_notes =
}}
|Section7={{Chembox Hazards
| ExternalSDS = [http://fscimage.fishersci.com/msds/27760.htm Fisher Scientific]
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| FlashPtC = 92.8
}}
|Section8={{Chembox Related
| OtherFunction_label = aromatics
| OtherFunction = carbazole, indole, isoindoline, oxindole
}}
}}
Indoline is an aromatic heterocyclic organic compound with the chemical formulation C8H9N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The compound is based on the indole structure, but the 2-3 bond is saturated. By oxidation/dehydrogenation it can be converted to indole.{{Katritzky2nd}}{{cite book |last=Clayden |first=J. |last2=Greeves |first2=N. |last3=Warren |first3=S. |last4=Wothers |first4=P. |title=Organic Chemistry |publisher=Oxford University Press |location=Oxford, Oxfordshire |year=2001 |isbn=0-19-850346-6 |url=https://archive.org/details/organicchemistry00clay_0 |url-access=registration }}
Indoline can be produced from the reaction of indole, zinc and 85% phosphoric acid.{{cite journal | last=Dolby | first=Lloyd J. | last2=Gribble | first2=Gordon W. | title=A convenient preparation of indoline | journal=Journal of Heterocyclic Chemistry | volume=3 | issue=2 | date=1966 | issn=0022-152X | doi=10.1002/jhet.5570030202 | pages=124–125}} It was used to make Indocaine.