Tetrahydroquinoline

Tetrahydroquinoline

Names
Preferred IUPAC name 1,2,3,4-Tetrahydroquinoline
Other names Hydroquinoline
Identifiers
CAS Number	635-46-1
3D model (JSmol)	Interactive image
Beilstein Reference	116149
ChEBI	CHEBI:213323
ChEMBL	ChEMBL303611
ChemSpider	62667
ECHA InfoCard
EC Number	211-237-6
E number
Gmelin Reference	27202
PubChem CID	69460
UNII	CCR50N1Z9G
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C9H11N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-2,4,6,10H,3,5,7H2 Key: LBUJPTNKIBCYBY-UHFFFAOYSA-N
SMILES C1CC2=CC=CC=C2NC1
Properties
Chemical formula	C9H11N
Molar mass	133.194 g·mol−1
Appearance	Colorless oily liquid
Density	1.0599 g/cm3
Melting point	20 °C (68 °F; 293 K)
Boiling point	251 °C (484 °F; 524 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H315, H319, H335, H350
Precautionary statements	P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Related compounds
Related compounds	Quinoline, Tetralin, Chromane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tetrahydroquinoline is an organic compound that is the semi-hydrogenated derivative of quinoline. It is a colorless oil.

Use

Substituted derivatives of tetrahydroquinoline are common in medicinal chemistry. Oxamniquine, dynemycin, viratmycin, and nicainoprol are bioactive tetrahydroquinolines. Typically tetrahydroquinoline derivatives are prepared by hydrogenation of the corresponding quinoline using heterogeneous catalysts.

Synthesis

Tetrahydroquinolines are produced by hydrogenation of quinolines. Because the hydrogenation is reversible, tetrahydroquinoline has been often examined as a hydrogen-donor solvent in coal liquifaction.

Using homogeneous catalysts, asymmetric hydrogenation has been demonstrated. It can also be prepared from 1-indanone (benzocyclopentanone).