1,2,3,4-Tetrahydroquinaldine

Base Information

• Chemical Name: 1,2,3,4-Tetrahydroquinaldine
• CAS No.: 1780-19-4
• Deprecated CAS: 1334-81-2
• Molecular Formula: C10H13N
• Molecular Weight: 147.22
• Hs Code.: 2901100000
• European Community (EC) Number: 246-996-2,277-887-8,217-226-2
• NSC Number: 65607
• UNII: XHV42AW48X
• DSSTox Substance ID: DTXSID50397311
• Nikkaji Number: J46.667K
• Wikipedia: 2-Methyltetrahydroquinoline
• ChEMBL ID: CHEMBL589607
• Mol file: 1780-19-4.mol

Synonyms:Quinaldine,1,2,3,4-tetrahydro- (6CI,7CI,8CI);1,2,3,4-Tetrahydro-2-methylquinoline;2-Methyl-1,2,3,4-tetrahydroquinoline;

Chemical Property of 1,2,3,4-Tetrahydroquinaldine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0.0152mmHg at 25°C
• Refractive Index: 1.522
• Boiling Point: 256.7 °C at 760 mmHg
• PKA: 5.15±0.40(Predicted)
• Flash Point: 113.3 °C
• PSA: 12.03000
• Density: 0.967 g/cm³
• LogP: 2.57120
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 147.104799419
• Heavy Atom Count: 11
• Complexity: 133

Purity/Quality:

97% ^*data from raw suppliers

1,2,3,4-Tetrahydroquinaldine >97.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=CC=CC=C2N1
• General Description: 1,2,3,4-Tetrahydroquinaldine (also known as 2-methyl-1,2,3,4-tetrahydroquinoline) is a hydrogenated derivative of quinaldine, where the aromatic ring is partially saturated. It can be synthesized via catalytic hydrogenation of quinaldine or quinoline derivatives using iridium-based catalysts under mild conditions, including atmospheric H₂ pressure and room temperature. The hydrogenation mechanism may proceed through an outer-sphere pathway involving sequential proton and hydride transfer. Additionally, asymmetric hydrogenation using chiral iridium catalysts, such as those with H8-BINAPO, P-Phos, SYNPHOS, or DIFLUORPHOS ligands, can yield enantiomerically enriched tetrahydroquinoline derivatives with high selectivity (up to 97% ee). The catalyst systems can also be immobilized in solvents like poly(ethylene glycol) dimethyl ether (DMPEG) for recyclability.

Technology Process of 1,2,3,4-Tetrahydroquinaldine

There total 160 articles about 1,2,3,4-Tetrahydroquinaldine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

1-methoxyamino-1-methylindane → 1,2,3,4-tetrahydro-2-methylquinoline (1780-19-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2h; Heating;

DOI:10.1039/c39930000147

Reference yield: 61.0%

N-(1-Methyl-3-phenyl-propyl)-hydroxylamine (65266-76-4) → 1,2,3,4-tetrahydro-2-methylquinoline (1780-19-4)

Guidance literature:

With trifluoroacetic acid; for 15h; Heating;

DOI:10.1248/cpb.29.1615

Reference yield: 57.0%

C12H17NO2 (71255-68-0) → 1,2,3,4-tetrahydro-2-methylquinoline (1780-19-4)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 6h; Ambient temperature;

DOI:10.1248/cpb.29.1615

upstream raw materials:

2-methylquinoline

4-hydroxy-2-methylquinoline

3,4-dichloro-2-chloromethyl-quinoline

4-(2-nitrobenzene)butan-2-one

Downstream raw materials:

1,5-diaminoanthraquinone

1-amino-5-nitroanthraquinone

1,5-bis-hydroxyamino-anthraquinone

2-methylquinoline