3-Bromo-5,6,7,8-tetrahydroquinoline

Base Information

• Chemical Name: 3-Bromo-5,6,7,8-tetrahydroquinoline
• CAS No.: 82132-68-1
• Molecular Formula: C9H10BrN
• Molecular Weight: 212.089
• Hs Code.: 2933499090
• European Community (EC) Number: 873-400-3
• DSSTox Substance ID: DTXSID20704396
• Nikkaji Number: J3.208.777I
• Wikidata: Q82636818
• Mol file: 82132-68-1.mol

Synonyms:3-bromo-5,6,7,8-tetrahydroquinoline;82132-68-1;MFCD11111668;SCHEMBL5120809;DTXSID20704396;AKOS015924456;PB43504;AS-36636;SY260113;CS-0102098;FT-0699028;A854053;QUINOLINE, 3-BROMO-5,6,7,8-TETRAHYDRO-

Chemical Property of 3-Bromo-5,6,7,8-tetrahydroquinoline

Chemical Property:

• Boiling Point: 260.3±40.0 °C(Predicted)
• PKA: 3.94±0.20(Predicted)
• PSA: 12.89000
• Density: 1.455±0.06 g/cm3(Predicted)
• LogP: 2.72290
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 210.99966
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

NLT 98% ^*data from raw suppliers

3-bromo-5,6,7,8-tetrahydroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2=C(C1)C=C(C=N2)Br

Technology Process of 3-Bromo-5,6,7,8-tetrahydroquinoline

There total 7 articles about 3-Bromo-5,6,7,8-tetrahydroquinoline 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%

1-(1-Cyclohexen-1-yl)pyrrolidine (1125-99-1) + 5-bromo-1,2,3-triazine (114078-88-5) → 3-bromo-5,6,7,8-tetrahydroquinoline (82132-68-1)

Guidance literature:

In chloroform; at 0 - 45 ℃; for 0.583333h; regioselective reaction;

DOI:10.1021/ja204856a

Reference yield:

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6,7,8-tetrahydroquinoline (1256360-50-5) → 3-bromo-5,6,7,8-tetrahydroquinoline (82132-68-1)

Guidance literature:

With copper(ll) bromide; In methanol; water; at 75 ℃; for 4h;

DOI:10.1002/anie.201208297

Reference yield:

hept-6-ynenitrile (15295-69-9) → 3-bromo-5,6,7,8-tetrahydroquinoline (82132-68-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / dicarbonyl(cyclopentadienyl)cobalt / m-xylene / Heating; Irradiation

2: 71 percent / Br₂ / CCl₄ / Ambient temperature

3: Me₄N⁽¹⁺⁾*F^(1-)

With tetramethylammonium fluoride; bromine; dicarbonylcyclopentadienylcobalt; In tetrachloromethane; m-xylene;

DOI:10.1039/c39820000133

upstream raw materials:

hept-6-ynenitrile

2,3-Bis-trimethylsilanyl-5,6,7,8-tetrahydro-quinoline

1-(1-Cyclohexen-1-yl)pyrrolidine

5-bromo-1,2,3-triazine

Downstream raw materials:

C₂₂H₂₂ClFN₄O

3-bromo-6,7-dihydroguinolin-8(5H)-one

Refernces

• 1、 -. "Cyclic gyrase and topoisomerase IV inhibitor". . . Retrieved 2017/01/02.
• 2、 Anderson, Erin D.,Boger, Dale L.. "Inverse electron demand diels-alder reactions of 1,2,3-triazines: Pronounced substituent effects on reactivity and cycloaddition scope". supporting information; experimental part. p. 12285 - 12292. Retrieved 2011/09/16.