Indoline

Indoline
Names
	Preferred IUPAC name 2,3-Dihydro-1H-indole
	Other names 2,3-Dihydroindole
Identifiers
CAS Number	496-15-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	111915
ChEBI	CHEBI:43295 ;
ChEMBL	ChEMBL388803 ;
ChemSpider	9905 ;
ECHA InfoCard	100.007.107
PubChem CID	10328;
RTECS number	NL6906300;
UNII	6DPT9AB2NK ;
CompTox Dashboard (EPA)	DTXSID9052133 ;
	InChI InChI=1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2 Key: LPAGFVYQRIESJQ-UHFFFAOYSA-N ; InChI=1/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2 Key: LPAGFVYQRIESJQ-UHFFFAOYAF;
	SMILES c1cccc2c1CCN2;
Properties
Chemical formula	C8H9N
Molar mass	119.16 g/mol
Appearance	Clear colourless liquid
Density	1.063 g/mL
Melting point	−21 °C (−6 °F; 252 K)
Boiling point	220 to 221 °C (428 to 430 °F; 493 to 494 K)
Hazards
Flash point	92.8 °C (199.0 °F; 365.9 K)
Safety data sheet (SDS)	Fisher Scientific
Related compounds
Related aromatics	carbazole, indole, isoindoline, oxindole
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.^[1]^[2]

Indoline can be produced from the reaction of indole, zinc and 85% phosphoric acid.^[3] It was used to make Indocaine.

References

^ Katritzky, A. R.; Pozharskii, A. F. (2000). Handbook of Heterocyclic Chemistry (2nd ed.). Academic Press. ISBN 0080429882.
^ Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001). Organic Chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.
^ Dolby, Lloyd J.; Gribble, Gordon W. (1966). "A convenient preparation of indoline". Journal of Heterocyclic Chemistry. 3 (2): 124–125. doi:10.1002/jhet.5570030202. ISSN 0022-152X.

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[Katritzky2nd-1] Katritzky, A. R.; Pozharskii, A. F. (2000). Handbook of Heterocyclic Chemistry (2nd ed.). Academic Press. ISBN 0080429882.

[Clayden1st-2] Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001). Organic Chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.

[3] Dolby, Lloyd J.; Gribble, Gordon W. (1966). "A convenient preparation of indoline". Journal of Heterocyclic Chemistry. 3 (2): 124–125. doi:10.1002/jhet.5570030202. ISSN 0022-152X.

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