{{chembox | Watchedfields = changed | verifiedrevid = 443873282 | Name = Indoline | ImageFile = Indoline numbering.svg | ImageName = Indoline | ImageFile1 = Indoline3d.png | ImageName1 = Indoline | PIN = 2,3-Dihydro-1''H''-indole | OtherNames = 2,3-Dihydroindole |Section1={{Chembox Identifiers | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 496-15-1 | Beilstein=111915 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 43295 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 388803 | ChemSpiderID = 9905 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | EC_number = 207-816-8 | Gmelin=27284 | PubChem = 10328 | RTECS = NL6906300 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 6DPT9AB2NK | SMILES = c1cccc2c1CCN2 | InChI = 1/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2 | InChIKey = LPAGFVYQRIESJQ-UHFFFAOYAF | 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 }} |Section2={{Chembox Properties | Appearance = Clear colourless liquid | Formula = C<sub>8</sub>H<sub>9</sub>N | 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 C<sub>8</sub>H<sub>9</sub>N. 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.<ref name="Katritzky2nd">{{Katritzky2nd}}</ref><ref name="Clayden1st">{{cite book |last1=Clayden |first1=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 }}</ref>
Indoline can be produced from the reaction of indole, zinc and 85% phosphoric acid.<ref>{{cite journal | last1=Dolby | first1=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}}</ref> It was used to make Indocaine.
== References == {{reflist}}
Category:Indolines
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