# Indoline

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Indoline
> Markdown URL: https://mediated.wiki/source/Indoline.md
> Source: https://en.wikipedia.org/wiki/Indoline
> Source revision: 1339571514
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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 = [aromatic](/source/aromatic)s
| OtherFunction = [carbazole](/source/carbazole), [indole](/source/indole), [isoindoline](/source/isoindoline), [oxindole](/source/oxindole)
  }}
}}

'''Indoline''' is an [aromatic](/source/aromatic) [heterocyclic](/source/Heterocyclic_compound) [organic compound](/source/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](/source/benzene) ring fused to a five-membered [nitrogen](/source/nitrogen)-containing ring. The compound is based on the [indole](/source/indole) structure, but the 2-3 [bond](/source/Chemical_bond) is [saturated](/source/Saturated_and_unsaturated_compounds). 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](/source/zinc) and 85% [phosphoric acid](/source/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

{{heterocyclic-stub}}

---
Adapted from the Wikipedia article [Indoline](https://en.wikipedia.org/wiki/Indoline) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Indoline?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.