1,2,3,4-Tetrahydroquinolin-3-amine

Base Information

• Chemical Name: 1,2,3,4-Tetrahydroquinolin-3-amine
• CAS No.: 40615-02-9
• Molecular Formula: C9H12 N2
• Molecular Weight: 148.208
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID00398818
• ChEMBL ID: CHEMBL159690
• Mol file: 40615-02-9.mol

Synonyms:1,2,3,4-tetrahydroquinolin-3-amine;40615-02-9;(+/-)-3-AMINO-1,2,3,4-TETRAHYDROQUINOLINE;1,2,3,4-TETRAHYDRO-3-QUINOLINAMINE;3-amino-1,2,3,4-tetrahydroquinoline;3-aminotetrahydroquinoline;CHEMBL159690;SCHEMBL2030277;DTXSID00398818;FBSQFLMMNVFTRT-UHFFFAOYSA-N;MFCD01318268;1,2,3,4-tetrahydroquinoline-3-amine;AKOS006283497;AB85821;CS-W021270;SB47618;DS-17044;3(R,S)-amino-1,2,3,4-tetrahydroquinoline;EN300-317240;A873276

Chemical Property of 1,2,3,4-Tetrahydroquinolin-3-amine

Chemical Property:

• Vapor Pressure: 2.34E-05mmHg at 25°C
• Boiling Point: 354.4°Cat760mmHg
• Flash Point: 168.2°C
• PSA: 38.05000
• Density: g/cm³
• LogP: 1.82020
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 148.100048391
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

NLT 98% ^*data from raw suppliers

1,2,3,4-Tetrahydroquinolin-3-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CNC2=CC=CC=C21)N
• Uses: 1,2,3,4-Tetrahydroquinolin-3-amine is used in the preparation of state-dependant NaV1.7 inhibitors for the treatment of neuropathic pain.

Technology Process of 1,2,3,4-Tetrahydroquinolin-3-amine

There total 2 articles about 1,2,3,4-Tetrahydroquinolin-3-amine 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: 68.0%

3-aminoquinoline (580-17-6) → 3(R,S)-amino-1,2,3,4-tetrahydroquinoline (40615-02-9,145554-63-8)

Guidance literature:

3-aminoquinoline; With H₂SiEt₂; tris(pentafluorophenyl)borate; In chloroform; at 100 ℃; for 24h; Inert atmosphere;

With hydrogenchloride; In diethyl ether; at 20 ℃; for 1h;

DOI:10.1055/s-0036-1588442

Reference yield:

3-aminoquinoline (580-17-6) → 3(R,S)-amino-1,2,3,4-tetrahydroquinoline (40615-02-9,145554-63-8) + bis-(1,2,3,4-tetrahydro-[3]quinolyl)-amine

Guidance literature:

With tetralin; nickel; at 55 ℃; under 66195.7 Torr; Hydrogenation;

Reference yield: 99.0%

3(R,S)-amino-1,2,3,4-tetrahydroquinoline (40615-02-9,145554-63-8) + Boc-D-Phe-OH (18942-49-9) → tert-butyl [(2R)-1-oxo-3-phenyl-1-(1,2,3,4-tetrahydroquinolin-3-ylamino)propan-2-yl]carbamate

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1248/cpb.c20-00126

upstream raw materials:

3-aminoquinoline

Downstream raw materials:

rac-8-[(2,6-difluorobenzyl)oxy]-2-methyl-N-(1,2,3,4-tetrahydroquinolin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide

Refernces

• 1、 Gandhamsetty, Narasimhulu,Park, Sehoon,Chang, Sukbok. "Boron-Catalyzed Hydrogenative Reduction of Substituted Quinolines to Tetrahydroquinolines with Hydrosilanes". supporting information. p. 2396 - 2400. Retrieved 2017/11/04.
• 2、 Glennon, Richard A.,Jacyno, John M.,Salley, John J.. "2,3-Dihydro and Carbocyclic Analogues of Tryptamines: Interaction with Serotonin Receptors". . p. 68 - 70. Retrieved 2007/10/02.