6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Base Information

• Chemical Name: 6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline
• CAS No.: 42835-89-2
• Molecular Formula: C10H12FN
• Molecular Weight: 165.21
• Hs Code.: 2933499090
• European Community (EC) Number: 255-963-1
• UNII: AZP5HK897S
• DSSTox Substance ID: DTXSID30962728
• Nikkaji Number: J309.984I
• Mol file: 42835-89-2.mol

Synonyms:6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline;FTHQ cpd

Chemical Property of 6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

Chemical Property:

• Appearance/Colour: white to yellowish crystalline low melting solid
• Melting Point: 31-33 °C
• Boiling Point: 254.6 °C at 760 mmHg
• PKA: 5.21±0.40(Predicted)
• Flash Point: 107.8 °C
• PSA: 12.03000
• Density: 1.056 g/cm³
• LogP: 2.71030
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 165.095377549
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

99% ^*data from raw suppliers

6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2=C(N1)C=CC(=C2)F
• Uses: Intermediate in the production of anti-cancer quinoline derivatives and antibacterial agents

Technology Process of 6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

There total 5 articles about 6-Fluoro-2-methyl-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: 99.0%

6-fluoro-2-methyl-quinoline (1128-61-6) + 4-formylphenylboronic acid, (87199-17-5) → 6-fluoro-2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-1,2,3,4-tetrahydroquinoline + 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline (42835-89-2)

Guidance literature:

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; In 1,2-dichloro-ethane; at 45 ℃; for 0.75h;

DOI:10.1021/acs.orglett.1c00302

Reference yield: 98.0%

6-fluoro-2-methyl-quinoline (1128-61-6) → 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline (42835-89-2)

Guidance literature:

With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; In dichloromethane; at 25 ℃; for 96h;

DOI:10.1055/s-2008-1042935

Reference yield:

trans-Crotonaldehyde (123-73-9,4170-30-3) + 4-fluoroaniline (371-40-4) → 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline (42835-89-2)

Guidance literature:

With ammonium acetate; platinum; In hydrogenchloride; methanol; water; acetic acid; isopropyl alcohol; acetone; toluene;

upstream raw materials:

6-fluoro-2-methyl-quinoline

trans-Crotonaldehyde

4-fluoroaniline

acetone

Downstream raw materials:

(R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

(S)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

6-fluoro-2-methyl-quinoline

Refernces

• 1、 Timelthaler, Daniel,Topf, Christoph. "Heterogeneous Hydrogenation of Quinoline Derivatives Effected by a Granular Cobalt Catalyst". . . Retrieved 2021/11/22.
• 2、 Adhikari, Priyanka,Bhattacharyya, Dipanjan,Nandi, Sekhar,Kancharla, Pavan K.,Das, Animesh. "Reductive Alkylation of Quinolines to N-Alkyl Tetrahydroquinolines Catalyzed by Arylboronic Acid". supporting information. p. 2437 - 2442. Retrieved 2021/04/05.