2-Methyltetrahydroquinoline

2-Methyltetrahydroquinoline
Names
	Preferred IUPAC name 2-Methyl-1,2,3,4-tetrahydroquinoline
	Other names Tetrahydroquinaldine, 1,2,3,4-Tetrahydroquinaldine
Identifiers
CAS Number	1780-19-4 ; (R): 63430-95-5 ; (S): 200125-70-8 ;
3D model (JSmol)	Interactive image ; (R): Interactive image ; (S): Interactive image ;
ChEMBL	ChEMBL589607 ;
ChemSpider	86920 ; (R): 1151452 ; (S): 1151451 ;
EC Number	217-226-2; racemic (R/S):277-887-8;
PubChem CID	96289 ; racemic (R/S): 1376640 ; (R): 1376639 ;
UNII	XHV42AW48X ;
CompTox Dashboard (EPA)	DTXSID80928096 ;
	InChI racemic (R/S):InChI=1S/C10H13N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-5,8,11H,6-7H2,1H3/t8-/m1/s1 Key: JZICUKPOZUKZLL-MRVPVSSYSA-N; (R):InChI=1S/C10H13N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-5,8,11H,6-7H2,1H3/t8-/m0/s1 Key: JZICUKPOZUKZLL-QMMMGPOBSA-N;
	SMILES CC1CCC2=CC=CC=C2N1; (R):C[C@@H]1CCC2=CC=CC=C2N1; (S):C[C@H]1CCC2=CC=CC=C2N1;
Properties
Chemical formula	C10H13N
Molar mass	147.221 g·mol−1
Appearance	colorless oil
Boiling point	125 °C (257 °F; 398 K) (17 Torr)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Last updated March 18, 2025

2-Methyltetrahydroquinoline is one of the methyl-substituted derivatives of tetrahydroquinoline. A colorless oil, it is a chiral compound owing to the presence of the methyl substituent. It is produced by the hydrogenation of quinaldine.^[1] It is of interest in medicinal chemistry.^[2]

References

↑ Chakraborty, Sumit; Brennessel, William W.; Jones, William D. (2014). "A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles". Journal of the American Chemical Society. 136 (24): 8564–8567. Bibcode:2014JAChS.136.8564C. doi:10.1021/ja504523b. PMID 24877556.
↑ Sridharan, Vellaisamy; Suryavanshi, Padmakar A.; Menéndez, J. Carlos (2011). "Advances in the Chemistry of Tetrahydroquinolines". Chemical Reviews. 111 (11): 7157–7259. doi:10.1021/cr100307m. PMID 21830756.

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[1] Chakraborty, Sumit; Brennessel, William W.; Jones, William D. (2014). "A Molecular Iron Catalyst for the Acceptorless Dehydrogenation and Hydrogenation of N-Heterocycles". Journal of the American Chemical Society. 136 (24): 8564–8567. Bibcode:2014JAChS.136.8564C. doi:10.1021/ja504523b. PMID 24877556.

[2] Sridharan, Vellaisamy; Suryavanshi, Padmakar A.; Menéndez, J. Carlos (2011). "Advances in the Chemistry of Tetrahydroquinolines". Chemical Reviews. 111 (11): 7157–7259. doi:10.1021/cr100307m. PMID 21830756.

[1]

[2]

Names

Preferred IUPAC name 2-Methyl-1,2,3,4-tetrahydroquinoline
Other names Tetrahydroquinaldine, 1,2,3,4-Tetrahydroquinaldine
Identifiers
CAS Number	1780-19-4 (R): 63430-95-5 (S): 200125-70-8
3D model (JSmol)	Interactive image (R): Interactive image (S): Interactive image
ChEMBL	ChEMBL589607
ChemSpider	86920 (R): 1151452 (S): 1151451
EC Number	217-226-2 racemic (R/S):277-887-8
PubChem CID	96289 racemic (R/S): 1376640 (R): 1376639
UNII	XHV42AW48X ^Y
CompTox Dashboard (EPA)	DTXSID80928096
InChI racemic (R/S):InChI=1S/C10H13N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-5,8,11H,6-7H2,1H3/t8-/m1/s1 Key: JZICUKPOZUKZLL-MRVPVSSYSA-N (R):InChI=1S/C10H13N/c1-8-6-7-9-4-2-3-5-10(9)11-8/h2-5,8,11H,6-7H2,1H3/t8-/m0/s1 Key: JZICUKPOZUKZLL-QMMMGPOBSA-N
SMILES CC1CCC2=CC=CC=C2N1 (R):C[C@@H]1CCC2=CC=CC=C2N1 (S):C[C@H]1CCC2=CC=CC=C2N1
Properties
Chemical formula	C₁₀H₁₃N
Molar mass	147.221 g·mol⁻¹
Appearance	colorless oil
Boiling point	125 °C (257 °F; 398 K) (17 Torr)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references