Indoline

Indoline
Indoline
Indoline
Names
Preferred IUPAC name
2,3-Dihydro-1H-indole
Other names
2,3-Dihydroindole
Identifiers
3D model (JSmol)
111915
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.107 Edit this at Wikidata
RTECS number
  • NL6906300
UNII
  • InChI=1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2 checkY
    Key: LPAGFVYQRIESJQ-UHFFFAOYSA-N checkY
  • InChI=1/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2
    Key: LPAGFVYQRIESJQ-UHFFFAOYAF
  • c1cccc2c1CCN2
Properties
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).
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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

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