6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: 6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 135631-91-3
• Molecular Formula: C11H14BrN^.HCl
• Molecular Weight: 240.143
• Hs Code.: 2933499090
• European Community (EC) Number: 839-077-8
• Mol file: 135631-91-3.mol

Synonyms:135631-91-3;6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline;6-bromo-4,4-dimethyl-2,3-dihydro-1H-quinoline;6-BROMO-4,4-DIMETHYL-1,2,3,4-TETRAHYDRO-QUINOLINE;Quinoline, 6-bromo-1,2,3,4-tetrahydro-4,4-dimethyl-;6-bromo-1,2,3,4-tetrahydro-4,4-dimethylQuinoline;6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline;hydrochloride;SCHEMBL1396642;WBOOAXJWGJAIMB-UHFFFAOYSA-N;MFCD09701997;AKOS024028374;SB33002;SY033774;CS-0279298;EN300-739656;F16236;A849498;4,4-Dimethyl-6-bromo-1,2,3,4-tetrahydroquinoline;6-bromo-4,4-dimethyl-2,3-dihydro-1H-quinoline hydrochloride

Chemical Property of 6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.542
• Boiling Point: 338 °C at 760 mmHg
• PKA: 4.33±0.40(Predicted)
• Flash Point: 158.2 °C
• PSA: 12.03000
• Density: 1.285g/cm³
• LogP: 3.68030
• Storage Temp.: Room temperature.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 239.03096
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

98%min ^*data from raw suppliers

6-Bromo-4,4-Dimethyl-2,3-Dihydro-1h-Quinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCNC2=C1C=C(C=C2)Br)C

Technology Process of 6-Bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline

There total 6 articles about 6-Bromo-4,4-dimethyl-1,2,3,4-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: 97.0%

4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline (135631-90-2) → 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (135631-91-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1016/S0960-894X(97)00435-6

Reference yield:

N-(3,3'-dimethylacryoloyl)-4-bromoaniline (135631-89-9) → 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (135631-91-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / AlCl₃ / a) from 130 deg C to 140 deg C, 1 h, b) 80 deg C, 0.5 h

2: 90 percent / borane-dimethyl sulfide / toluene / a) 0 deg C, 15 min, b) reflux, 5 h

With aluminium trichloride; dimethylsulfide borane complex; In toluene;

DOI:10.1021/jm970196m

Reference yield:

3,3-Dimethylacryloyl chloride (3350-78-5) → 6-bromo-4,4-dimethyl-1,2,3,4-tetrahydroquinoline (135631-91-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / CHCl₃ / 5 h / Heating

2: 65 percent / AlCl₃ / a) from 130 deg C to 140 deg C, 1 h, b) 80 deg C, 0.5 h

3: 90 percent / borane-dimethyl sulfide / toluene / a) 0 deg C, 15 min, b) reflux, 5 h

With aluminium trichloride; dimethylsulfide borane complex; In chloroform; toluene;

DOI:10.1021/jm970196m

upstream raw materials:

4,4-dimethyl-6-bromo-2-oxo-1,2,3,4-tetrahydroquinoline

3,3-Dimethylacryloyl chloride

4-bromo-aniline

N-(3,3'-dimethylacryoloyl)-4-bromoaniline

Refernces

• 1、 Gnanasekaran, Krishna Kumar,Pouland, Tim,Bunce, Richard A.,Darrell Berlin,Abuskhuna, Suaad,Bhandari, Dipendra,Mashayekhi, Maryam,Zhou, Donghua H.,Benbrook, Doris M.. "Tetrahydroquinoline units in flexible heteroarotinoids (Flex-Hets) convey anti-cancer properties in A2780 ovarian cancer cells". . . Retrieved 2019/12/24.
• 2、 Juen, Ludovic,Brachet-Botineau, Marie,Parmenon, Cécile,Bourgeais, Jér?me,Hérault, Olivier,Gouilleux, Fabrice,Viaud-Massuard, Marie-Claude,Prié, Gildas. "New Inhibitor Targeting Signal Transducer and Activator of Transcription 5 (STAT5) Signaling in Myeloid Leukemias". . p. 6119 - 6136. Retrieved 2017/08/02.