4-Fluoroquinoline

Base Information

• Chemical Name: 4-Fluoroquinoline
• CAS No.: 394-70-7
• Molecular Formula: C9H6 F N
• Molecular Weight: 147.152
• Hs Code.: 2933499090
• European Community (EC) Number: 840-362-4
• DSSTox Substance ID: DTXSID80192593
• Nikkaji Number: J616.787J
• Wikidata: Q83065255
• Mol file: 394-70-7.mol

Synonyms:4-Fluoroquinoline;394-70-7;Quinoline, 4-fluoro-;CCRIS 3738;BRN 0114549;4-20-00-03375 (Beilstein Handbook Reference);SCHEMBL1054409;DTXSID80192593;MFCD01685510;AKOS006282378;SB67778;TS-01917;LS-141956;CS-0136565;FT-0660390;EN300-253650;A847254

Chemical Property of 4-Fluoroquinoline

Chemical Property:

• Vapor Pressure: 0.0654mmHg at 25°C
• Melting Point: 180-195 °C
• Boiling Point: 238.4°Cat760mmHg
• PKA: 3.87±0.13(Predicted)
• Flash Point: 98°C
• PSA: 12.89000
• Density: 1.216g/cm³
• LogP: 2.37390
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 147.048427358
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Fluoroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=N2)F
• Uses: A fluorinated quinilone that in the presence of microsomal activation exhibits some mutagenic activity in Salmonella typhimurium TA100 but showed no significant effect on unscheduled DNA synthesis (UDS) in rat hepatocytes compared to other fluoroquinones.

Technology Process of 4-Fluoroquinoline

There total 5 articles about 4-Fluoroquinoline 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: 74.0%

4-bromoquinoline (3964-04-3,850917-90-7) → 4-Fluoroquinoline (394-70-7)

Guidance literature:

With silver fluoride; bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; In toluene; at 130 ℃; for 18h; Sealed tube;

Reference yield: 3.0%

4-aminoquinoline (578-68-7) → 4-Fluoroquinoline (394-70-7)

Guidance literature:

4-aminoquinoline; With tetrafluoroboric acid; sodium nitrite; In water; at -10 ℃; for 0.166667h;

In diethyl ether; at 20 ℃; for 0.5h;

DOI:10.1021/jacs.7b03131

Reference yield:

4-chloroquinoline (611-35-8) → 4-Fluoroquinoline (394-70-7)

Guidance literature:

With tetramethylammonium fluoride; In dimethyl sulfoxide; at 80 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.1c01490

upstream raw materials:

4-aminoquinoline

acetaldehyde

2-(trifluoromethyl)benzenamine

4-bromoquinoline

Downstream raw materials:

6-fluoroquinoline

4-fluoro-benzenesulfonic acid-(6-fluoro-[8]quinolylamide)

6-fluoro-8-nitroquinoline

8-amino-6-fluoroquinoline

Refernces

• 1、 Taylor, Nicholas J.,Emer, Enrico,Preshlock, Sean,Schedler, Michael,Tredwell, Matthew,Verhoog, Stefan,Mercier, Joel,Genicot, Christophe,Gouverneur, Véronique. "Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands". supporting information. p. 8267 - 8276. Retrieved 2017/06/27.
• 2、 Noel, Timothy,Maimone, Thomas J.,Buchwald, Stephen L.. "Accelerating palladium-catalyzed C-F bond formation: Use of a microflow packed-bed reactor". supporting information; experimental part. p. 8900 - 8903. Retrieved 2011/10/19.