2,2,4-Trimethyl-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: 2,2,4-Trimethyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 4497-58-9
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• Hs Code.: 2933499090
• European Community (EC) Number: 224-791-9
• DSSTox Substance ID: DTXSID20884081
• Nikkaji Number: J205.868E
• Mol file: 4497-58-9.mol

Synonyms:2,2,4-Trimethyl-1,2,3,4-tetrahydroquinoline;4497-58-9;1,2,3,4-Tetrahydro-2,2,4-trimethylquinoline;Quinoline, 1,2,3,4-tetrahydro-2,2,4-trimethyl-;2,2,4-trimethyl-3,4-dihydro-1H-quinoline;EINECS 224-791-9;SCHEMBL592819;DTXSID20884081;AMY41314;MFCD00957562;STK789028;AKOS000270107;AKOS016039956;WS-02110;CS-0117575;FT-0650949;EN300-88608;W16294;A1-24385;W-109976;F2196-0024

Chemical Property of 2,2,4-Trimethyl-1,2,3,4-tetrahydroquinoline

Chemical Property:

• Vapor Pressure: 0.0247mmHg at 25°C
• Refractive Index: 1.497
• Boiling Point: 248.1°Cat760mmHg
• Flash Point: 101.3°C
• PSA: 12.03000
• Density: 0.919g/cm³
• LogP: 3.52230
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 175.136099547
• Heavy Atom Count: 13
• Complexity: 186

Purity/Quality:

99.9% ^*data from raw suppliers

2,2,4-Trimethyl-1,2,3,4-tetrahydroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(NC2=CC=CC=C12)(C)C
• Uses: 2,2,4-Trimethyl-1,2,3,4-tetrahydroquinoline is a reagent in the synthesis of tetrahydroquinoline sensitizers used for dye-sensitized solar cells. 2,2,4-Trimethyl-1,2,3,4-tetrahydroquinoline is also a reagent in the preparation of tetra- and pentacyclic derivatives of phenothiazinium photosensitizers which are used as photoantimicrobial agents.

Technology Process of 2,2,4-Trimethyl-1,2,3,4-tetrahydroquinoline

There total 7 articles about 2,2,4-Trimethyl-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%

2,2,4-trimethyl-1,2-dihydroquinoline (147-47-7,26780-96-1,389806-19-3) → 1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (4497-58-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 5h;

DOI:10.1039/b100060h

Reference yield: 58.0%

1-methyl-3,4-benzo-7-thia-2-azabicyclo<3.3.1>nonane (106718-61-0) → 1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (4497-58-9)

Guidance literature:

With hydrogen; nickel; In ethanol; at 100 ℃; for 62h; under 2280 Torr;

DOI:10.1248/cpb.34.1917

Reference yield:

2-methylquinoline (91-63-4) → 1,2,3,4-tetrahydro-2,2,4-trimethylquinoline (4497-58-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / NaH / dimethylsulfoxide / 3.5 h / 70 °C

2: 72 percent / HCl / Zn-Hg / acetic acid / 1 h / 95 °C

3: 58 percent / H₂ / Raney Ni / ethanol / 62 h / 100 °C / 2280 Torr

With hydrogenchloride; hydrogen; sodium hydride; nickel; mercury; zinc; In ethanol; acetic acid; dimethyl sulfoxide;

DOI:10.1248/cpb.34.1917

upstream raw materials:

2,2,4-trimethyl-1,2-dihydroquinoline

1-methyl-3,4-benzo-7-thia-2-azabicyclo<3.3.1>nonane

ethanol

2-methylquinoline

Downstream raw materials:

1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinoline

(E)-ethyl 2-cyano-2-(5,5-dimethyl-3-((E)-2-(1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinolin-6-yl)vinyl)cyclohex-2-enylidene)acetate

(E)-2-cyano-2-(5,5-dimethyl-3-((E)-2-(1,2,2,4-tetramethyl-1,2,3,4-tetrahydroquinolin-6-yl)vinyl)cyclohex-2-enylidene)acetic acid

4-amino-1,1,3-trimethylindane

Refernces

• 1、 Cheng, Ming,Yang, Xichuan,Li, Jiajia,Zhang, Fuguo,Sun, Licheng. "Co-sensitization of organic dyes for efficient dye-sensitized solar cells". . p. 70 - 77. Retrieved 2013/03/13.
• 2、 Cheng, Ming,Yang, Xichuan,Li, Jiajia,Chen, Cheng,Zhao, Jianghua,Wang, Yu,Sun, Licheng. "Dye-sensitized solar cells based on a donor-acceptor system with a pyridine cation as an electron-withdrawing anchoring group". supporting information. p. 16196 - 16202. Retrieved 2013/02/23.