76916-51-3

Basic information

• Product Name: 2-Propyl-1,2,3,4-tetrahydro-quinoline
• Synonyms: 2-Propyl-1,2,3,4-tetrahydro-quinoline
• CAS NO: 76916-51-3
• Molecular Formula: C₁₂H₁₇N
• Molecular Weight: 175.27008
• Mol File: 76916-51-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Propyl-1,2,3,4-tetrahydro-quinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propyl-1,2,3,4-tetrahydro-quinoline(76916-51-3)
• EPA Substance Registry System: 2-Propyl-1,2,3,4-tetrahydro-quinoline(76916-51-3)

Safety Data

• Hazardous Substances Data: 76916-51-3(Hazardous Substances Data)

Upstream product

• 7647-01-0 hydrogenchloride 
• 1613-32-7 2-n-Propylquinoline 
• 58173-64-1 2-Cyclopropylquinoline 
• 5344-90-1 2-Aminobenzyl alcohol 
• 6032-29-7 (+/-)-2-pentanol 
• 612-62-4 2-Chloroquinoline 
• 1087319-29-6 1-(1-phenylethyl)-2-propyl-1,2,3,4-tetrahydroquinoline 
• 529-23-7 o-aminobenzaldehyde 
• 107-87-9 2-Pentanone 
• 3947-76-0 N-methylquinolinium iodide 
• 375395-22-5 1-methyl-2-propyl-1,2,3,4-tetrahydroquinoline 
• 859958-79-5 1-methyl-2-propyl-1,2-dihydro-quinoline 
• 615-36-1 2-bromoaniline 
• 62-53-3 aniline 

Downstream Products

• 1613-32-7 2-n-Propylquinoline 

Relevant articles and documents

Synthesis of Tetrahydroquinolines via Borrowing Hydrogen Methodology Using a Manganese PN3Pincer Catalyst

A straightforward and selective synthesis of 1,2,3,4-tetrahydroquinolines starting from 2-aminobenzyl alcohols and simple secondary alcohols is reported. This one-pot cascade reaction is based on the borrowing hydrogen methodology promoted by a manganese(I) PN3 pincer complex. The reaction selectively leads to 1,2,3,4-tetrahydroquinolines thanks to a targeted choice of base. This strategy provides an atom-efficient pathway with water as the only byproduct. In addition, no further reducing agents are required.

Unsupported nanoporous gold catalyst for highly selective hydrogenation of quinolines

For the first time, the highly efficient and regioselective hydrogenation of quinoline derivatives to 1,2,3,4-tetrahydroquinolines using unsupported nanoporous gold (AuNPore) as a catalyst and organosilane with water as a hydrogen source is reported. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity.

The remarkable effect of a simple ion: Iodide-promoted transfer hydrogenation of heteroaromatics

I can do it! Accelerated by simple iodide ions, rhodium-catalysed transfer hydrogenation can be readily performed on quinolines, isoquinolines and quinoxalines, affording the tetrahydro products in high yields with low catalyst loading (see scheme). Copyright

Synthesis of alkaloids of Galipea officinalis by alkylation of an α-amino nitrile

A new synthetic approach directed towards the synthesis of naturally occurring 2-alkyl-tetrahydroquinolines is described. The C-C bonds in the α position relative to the nitrogen atom were formed by the reversal of the polarity of the C=N bond of α-amino nitrile 6, which was prepared electrochemically from 1-(phenylethyl)-tetrahydroquinoline. A NaBH 4-mediated reductive decyanation process furnished benzylic amines 16a-d as mixtures of diastereomers (50-60% de). The catalytic hydrogenolysis of these amines was performed in the presence of Pearlman's catalyst to give the tetrahydroquinolines 17a-d in yields ranging from 70% to 95%. Methylation of the free nitrogen atom afforded the title compounds 1-4 in 70-90% yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Indium metal as a reducing agent in organic synthesis

The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and α-oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.

Switching Androgen Receptor Antagonists to Agonists by Modifying C-Ring Substituents on Piperidinoquinolinone

New nonsteroidal human androgen receptor (hAR) agonists were developed from an hAR antagonist pharmacophore, 2(1H-piperidinoquinolinone. (+/-)-trans-7,8-diethyl-4-trifluoromethyl-2(1H)-piperidinoquinolinone was synthesized and demonstrated p

Regioselectivity in Forming Dipole-Stabilized Anions. Sites of Metalation of Indolines, Tetrahydroquinolines, and Benzazepines Activated by N-Formimidoyl or N-Boc Groups

Metalation of the title compounds indicated that the formamidine-equipped indolines or 1,2,3,4-tetrahydroquinolines give rise solely to C-2 alkylation products (5,6) whereas the corresponding N-t-Boc systems give only ortho aryl alkylation (7,8).

Palladium-Assisted N-Alkylation of Indoles: Attempted Application to Polycyclization

The palladium(II) complexes of the olefins ethene, propene, and 1-hexene reacted with 1-lithioindole to produce N-alkylated indoles exclusively.Attempts to perform this N-alkylation intramoleculary (to form tricyclic material from 2-allylskatole) failed.Anilines with dienic side chains in the 2-position were subjected to Pd(II)-assisted cyclization conditions in attempts to induce polycyclization.However, only monocyclization was observed.