394-69-4|5-Fluoroquinoline| Ambeed

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Quality Control of [ 394-69-4 ] Purity: 95% SDS Specification

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Product Citations

Systematic analysis of gut bacterial carcinogen metabolism and its functional consequences

Boyao Zhang ; George-Eugen Maftei ; Bartosz Bartmanski ; Michael Zimmermann ;

DOI: 10.1101/2024.05.20.595058 bioRxiv,2024:2024.05.20.595058.

Abstract: Organic carcinogens, in particular DNA-reactive compounds, contribute to the irreversible initiation step of tumorigenesis through introduction of genomic instability. Although carcinogen bioactivation and detoxification by human enzymes has been extensively studied, carcinogen biotransformation by human-associated bacteria, the microbiota, has not yet been systematically investigated. We tested the biotransformation of 68 mutagenic carcinogens by 34 bacterial species representative for the upper and lower human gastrointestinal tract and found that the majority (41) of the tested carcinogens undergo bacterial biotransformation. To assess the functional consequences of microbial carcinogen metabolism, we developed a pipeline to couple gut bacterial carcinogen biotransformation assays with Ames mutagenicity testing and liver biotransformation experiments. This revealed a bidirectional crosstalk between gut microbiota and host carcinogen metabolism, which we validated in gnotobiotic mouse models. Overall, the systematic assessment of gut microbiota carcinogen biotransformation and its interplay with host metabolism highlights the gut microbiome as an important modulator of exposome-induced tumorigenesis.

Purchased from AmBeed: 446-86-6 ; 121-66-4 ; 607-35-2 ; 67-20-9 ; 105650-23-5 ; 59-87-0 ; 117-39-5 ; 57-97-6 ; 5131-60-2 ; 512-56-1 ; 62-44-2 ; 6959-48-4 ; 84-65-1 ; 137-17-7 ; 117-39-5 ; 153-78-6 ; 1614-12-6 ; 298-81-7 ; 404-86-4 ; 320-67-2 ; 99-55-8 ; 94-52-0 ; 2832-40-8 ; 101-61-1 ; 103-33-3 ; 114-83-0 ; 64091-91-4 ; 53-96-3 ; 3817-11-6 ; 90-94-8 ; 613-13-8 ; 56-57-5 ; 91-64-5 ; 26148-68-5 ; 101-80-4 ; 139-65-1 ; 366-70-1 ; 389-08-2 ; 99-59-2 ; 132-32-1 ; 394-69-4 ; 3544-23-8 ; 389-08-2 ; 320-67-2 ; 82-28-0 ; 2475-45-8 ; 129-15-7

Product Details of [ 394-69-4 ]

CAS No. :	394-69-4
Formula :	C₉H₆FN
M.W :	147.15
SMILES Code :	FC1=CC=CC2=C1C=CC=N2
MDL No. :	MFCD01685511
InChI Key :	WMFXCDGQRHJFKL-UHFFFAOYSA-N
Pubchem ID :	115243

Safety of [ 394-69-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H320-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 394-69-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	41.7
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	12.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.86
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.94
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.79
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.27
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.91
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.35

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.65
Solubility	0.332 mg/ml ; 0.00225 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.84
Solubility	2.15 mg/ml ; 0.0146 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.96
Solubility	0.0162 mg/ml ; 0.00011 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.82 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	2.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.57

Application In Synthesis of [ 394-69-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 394-69-4 ]

[ 394-69-4 ] Synthesis Path-Downstream 1~32

2
quinoline-5-diazonium-tetrafluoroborate [ No CAS ]
[ 394-69-4 ]

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 1785.

3
[ 611-34-7 ]
[ 394-69-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With tetrafluoroboric acid; sodium nitrite; at 0℃; for 1h;	Preparation LIII 5-fluoro-1,2,3,4-tetrahydroquinoline [0363] 5-fluoroquinoline [0364] To a suspension of 5-aminoquinoline (50 g, 347 mmol) in 48percent HBF4 (200 mL) at 0° C. was added portionwise sodium nitrite. This was stirred for 1 hour and then poured into 1:1 ethyl acetate/diethyl ether (500 mL). The resulting suspension was filtered and the solid dried. This solid (82.5 g, 338 mmol) was added portionwise to refluxing xylene (1 L) and stirred for 2 hours then allowed to cool. The xylene was decanted off and the residue dissolved in 1N hydrochloric acid (600 mL). After neutralization with sodium carbonate, the mixture was extracted with ethyl acetate (10.x.500 mL). The extracts were dried over sodium sulfate, filtered and the volatiles removed under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 10-20percent diethyl ether in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 28.1 g (55percent) of the desired compound. MS (EI, m/z) C9H6FN (M+1) 148.0 [0365] Reduction [0366] A mixture of 5-fluoroquinoline (28.1 g), 5percent palladium on carbon (5.6 g) in methanol was shaken over night at 40° C. under 60 psi hydrogen. The mixture was filtered through celite and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5-10percent ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 22.5 g (78percent) of the title compound. [0367] MS (EI, m/z) C9H10FN (M+1) 152.0
24.5%	With tetrafluoroboric acid; sodium nitrite; In xylene; at 0℃;Reflux;	To a suspension of 5-aminoquinoline (lO.Og, 0.069 mol) in 48percent HBF4 (40 mL) at 0°C was added portionwise sodium nitrite. This was stirred for 1 hour and then poured into 1 : 1 ethyl acetate/diethyl ether (50 mL). The resulting suspension was filtered and the solid dried. This solid was added portionwise to refluxing xylene (80 mL) and stirred for 2 hours then allowed to cool. The xylene was decanted off and the residue was dissolved in IN aqueous hydrochloric acid (100 mL). After neutralization with sodium carbonate, the mixture was extracted with ethyl acetate (3 x 80 mL). The extracts were dried over sodium sulfate, filtered and the volatiles were removed in vacuo. The residue was purified by silica gel column chromatography, eluting with 2percent ethyl acetate in petroleum ether to afford 5-fluoroquinoline as a colorless oil (2.5 g, 24.5percent).'H-NMR (300 MHz, CDC13) delta 8.93 - 8.98 (m, 1H), 8.43 - 8.46 (m, H), 7.92 (d, / = 8.4 Hz, 1H), 7.62 - 7.78 (m, 1H), 7.41 - 7.49 (m, 1H), 7.22 - 7.26 (m, 1H)
800 mg	With tetrafluoroboric acid; sodium nitrite; at 0℃; for 1h;	To a solution of quinolin-5 -amine (2 g, 13.9 mmol) in 10 mL of 48percent HBF4 at 0°C was added sodium nitrite (933 mg, 13.5 mmol) portionwise. This was stirred for 1 hour and then poured into 1 : 1 ethyl acetate diethyl ether mixture (50 mL). The resulting suspension was filtered and the solid was dried. This solid was added portionwise to refluxing xylene (30 mL) and stirred for 3 hours, then allowed to cool. The xylene was decanted off and the residue was dissolved in IN HC1 (50 mL). After neutralization with NaHC03, the mixture was extracted with ethyl acetate (3 x 50 mL). The extracts were dried over sodium sulfate, filtered and the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography (3percent EtOAc/PE) to afford 800 mg of title compound as colorless oil. LC-MS: m/z 148.2 (M+H)+

800 mg	With tetrafluoroboric acid; sodium nitrite; at 0℃; for 1h;	To a solution of quinolin-5-amine (2 g, 13.9 mmol) in 10 mL of 48percent HBF4 at 0° C. was added sodium nitrite (933 mg, 13.5 mmol) portionwise. This was stirred for 1 hour and then poured into 1:1 ethyl acetate diethyl ether mixture (50 mL). The resulting suspension was filtered and the solid was dried. This solid was added portionwise to refluxing xylene (30 mL) and stirred for 3 hours, then allowed to cool. The xylene was decanted off and the residue was dissolved in 1N HCl (50 mL). After neutralization with NaHCO3, the mixture was extracted with ethyl acetate (3×50 mL). The extracts were dried over sodium sulfate, filtered and the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography (3percent EtOAc/PE) to afford 800 mg of title compound as colorless oil. LC-MS: m/z 148.2 (M+H)+
800 mg	With tetrafluoroboric acid; sodium nitrite; at 0℃; for 1h;	To a solution of quinolin-5 -amine (2 g, 13.9 mmol) in 10 mL of 48percent HBF4 at 0°C was added sodium nitrite (933 mg, 13.5 mmol) portionwise. This was stirred for 1 hour and then poured into 1 : 1 ethyl acetate diethyl ether mixture (50 mL). The resulting suspension was filtered and the solid was dried. This solid was added portionwise to refluxing xylene (30 mL) and stirred for 3 hours, then allowed to cool. The xylene was decanted off and the residue was dissolved in IN HC1 (50 mL). After neutralization with NaHC03, the mixture was extracted with ethyl acetate (3 x 50 mL). The extracts were dried over sodium sulfate, filtered and the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography (3percent EtOAc/PE) to afford 800 mg of title compound as colorless oil. LC-MS: m/z 148.2 (M+H)+

References: [1]Patent: US2003/229026,2003,A1 .Location in patent: Page 25.
[2]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2611 - 2623.
[3]Patent: WO2012/94462,2012,A2 .Location in patent: Page/Page column 75.
[4]Biological and Pharmaceutical Bulletin,1997,vol. 20,p. 646 - 650.
[5]Patent: WO2014/139144,2014,A1 .Location in patent: Page/Page column 179.
[6]Patent: US2014/288081,2014,A1 .Location in patent: Paragraph 0738; 0739.
[7]Patent: WO2014/139325,2014,A1 .Location in patent: Page/Page column 192; 193.
[8]Journal of Medicinal Chemistry,2017,vol. 60,p. 6998 - 7011.

4
[ 394-69-4 ]
[ 152167-85-6 ]

References: [1]Biological and Pharmaceutical Bulletin,1997,vol. 20,p. 646 - 650.

5
[ 91-22-5 ]
[ 396-30-5 ]
[ 394-68-3 ]
[ 394-69-4 ]
[ 16650-32-1 ]

References: [1]Journal of Fluorine Chemistry,2002,vol. 117,p. 99 - 101.

6
[ 394-69-4 ]
[ 2338-73-0 ]

References: [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2611 - 2623.
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 6998 - 7011.

7
[ 394-69-4 ]
5-fluoro-6-nitroquinoline [ No CAS ]

References: [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2611 - 2623.

8
[ 91-22-5 ]
[ 394-68-3 ]
[ 394-69-4 ]
[ 16650-32-1 ]
5,6-difluoro-5,6-dihydroquinoline [ No CAS ]

References: [1]Journal of Fluorine Chemistry,2004,vol. 125,p. 661 - 671.

9
[ 372-19-0 ]
[ 56-81-5 ]
[ 396-32-7 ]
[ 394-69-4 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 2666 - 2676.

10
[ 394-69-4 ]
[ 455955-27-8 ]

References: [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2611 - 2623.

11
[ 394-69-4 ]
[ 455955-29-0 ]

References: [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2611 - 2623.

12
[ 394-69-4 ]
4-(5-fluoro-quinolin-2-yl)-piperazine-1-carbaldehyde [ No CAS ]

References: [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2611 - 2623.

13
[ 394-69-4 ]
[ 455955-34-7 ]

References: [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2611 - 2623.

14
[ 394-69-4 ]
1-[4-(6-nitro-5-fluoroquinolin-2-yl)piperazin-1-yl]ethanone [ No CAS ]

References: [1]Bioorganic and medicinal chemistry,2002,vol. 10,p. 2611 - 2623.

15
[ 394-69-4 ]
5-fluoro-1,10-phenanthroline [ No CAS ]

References: [1]Biological and Pharmaceutical Bulletin,1997,vol. 20,p. 646 - 650.

16
[ 394-69-4 ]
[ 161038-18-2 ]

References: [1]Biological and Pharmaceutical Bulletin,1997,vol. 20,p. 646 - 650.

17
[ 394-69-4 ]
5-fluoro-1,2,3,4-tetrahydroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogen;5%-palladium/activated carbon; In methanol; at 40℃; under 3102.97 Torr;	Reduction; Shake a mixture of <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (28.1 g) and 5percent palladium on carbon (5.6 g) in methanol over night at 40°C under 60 psi hydrogen. Filter the mixture through Celite and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 5-10percent ethyl acetate in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the title compound (22.5 g, 78percent). MS (EI, m/z) CgHloFN (M+1) 152.0
78%	With hydrogen;5% palladium over charcoal; In methanol; at 40℃; under 3102.97 Torr;Under hydrogen;	Preparation LIII 5-fluoro-1,2,3,4-tetrahydro<strong>[394-69-4]quinoline</strong> [0363] <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> [0364] To a suspension of 5-amino<strong>[394-69-4]quinoline</strong> (50 g, 347 mmol) in 48percent HBF4 (200 mL) at 0° C. was added portionwise sodium nitrite. This was stirred for 1 hour and then poured into 1:1 ethyl acetate/diethyl ether (500 mL). The resulting suspension was filtered and the solid dried. This solid (82.5 g, 338 mmol) was added portionwise to refluxing xylene (1 L) and stirred for 2 hours then allowed to cool. The xylene was decanted off and the residue dissolved in 1N hydrochloric acid (600 mL). After neutralization with sodium carbonate, the mixture was extracted with ethyl acetate (10.x.500 mL). The extracts were dried over sodium sulfate, filtered and the volatiles removed under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 10-20percent diethyl ether in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 28.1 g (55percent) of the desired compound. MS (EI, m/z) C9H6FN (M+1) 148.0 [0365] Reduction [0366] A mixture of <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (28.1 g), 5percent palladium on carbon (5.6 g) in methanol was shaken over night at 40° C. under 60 psi hydrogen. The mixture was filtered through celite and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5-10percent ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 22.5 g (78percent) of the title compound. [0367] MS (EI, m/z) C9H10FN (M+1) 152.0
70%	With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃;	Palladium on carbon (10percent, 1.25 g) was added to a solution of <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (2.5 g, 16.99 mmol) in methanol and the reaction was overnight at room temperature under an atmosphere of hydrogen. The reaction mixture was filtered through Celite and concentrated in vacuo to afford 5-fluoro-l ,2,3,4-tetrahydro<strong>[394-69-4]quinoline</strong> as a colorless oil (1.80 g, 70 percent).LC/MS (ES, m/z) [M+H]+ 152.0'H-NMR (300 MHz, CDCI3) delta 6.87 - 6.95 (m, 2H), 6.26 - 6.40 (m, 2H), 3.28 - 3.31 (m, 2H), 2.72 - 2.77 (t, / = 6.60 Hz, 2H), 1.92 - 1.98 (m, 2H)

References: [1]Patent: WO2003/76442,2003,A1 .Location in patent: Page/Page column 22.
[2]Patent: US2003/229026,2003,A1 .Location in patent: Page 25.
[3]Patent: WO2012/94462,2012,A2 .Location in patent: Page/Page column 75.

18
5-(diazonium)chinolinyl tetrafluoroborate [ No CAS ]
[ 394-69-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	In xylene; for 2h;Heating / reflux;	Preparation 1 5-fluoro-1, 2,3, 4-tetrahydroquinoline; 5-fluoroquinoline; Add sodium nitrite in portions to a suspension of 5-aminoquinoline (50 g, 347 mmol) in 4Spercent HBF4 (200 mL) at 0°C. Stir for 1 hour and then pour into 1: 1 diethyl ether/ethyl acetate (500 mL). Filter the resulting suspension and dry the solid. Add this solid (82.5 g, 338 mmol) in portions to refluxing xylene (1 L), stir for 2 hours, and then cool. Decant the xylene and dissolve the residue in 1N hydrochloric acid (600 mL). Neutralize with sodium carbonate, extract with ethyl acetate (10 x 500 mL), dry the extracts over sodium sulfate, filter and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 10-20percent diethyl ether in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the desired compound (28.1 g, 55percent). MS (EI, m/z) C9H6FN (M+1) 148.0

References: [1]Patent: WO2003/76442,2003,A1 .Location in patent: Page/Page column 22.
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 6998 - 7011.

19
[ 394-69-4 ]
[ 53425-61-9 ]
[ 511234-63-2 ]

Yield	Reaction Conditions	Operation in experiment
		a) 1-Benzoyl-2-cyano-5-fluoro-1,2-dihydro<strong>[394-69-4]quinoline</strong> (Compound 78A) The title compound was prepared as described for compound 32A, but starting from <strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (WO 0144247) instead of 6-methyl<strong>[394-69-4]quinoline</strong>. (46percent) 1H-NMR (delta): 6.13-6.22 (m; 1H), 6.41 (d; 1H), 6.79-7.02 (m; 2H), 7.18-7.37 (m; 7H).

References: [1]Patent: US2003/162777,2003,A1 .

20
[ 177734-78-0 ]
[ 394-69-4 ]

References: [1]Science,2009,vol. 325,p. 1661 - 1664.
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 8900 - 8903.

21
[ 4964-71-0 ]
[ 394-69-4 ]

References: [1]Journal of the American Chemical Society,2014,vol. 136,p. 3792 - 3795.
[2]Applied Catalysis A: General,2011,vol. 394,p. 191 - 194.

22
[ 394-69-4 ]
[ 1384852-13-4 ]

References: [1]Patent: WO2012/94462,2012,A2 .

23
[ 394-69-4 ]
[ 1384850-70-7 ]

References: [1]Patent: WO2012/94462,2012,A2 .

24
[ 394-69-4 ]
[ 1384850-71-8 ]

References: [1]Patent: WO2012/94462,2012,A2 .

25
[ 394-69-4 ]
[ 1384852-14-5 ]

References: [1]Patent: WO2012/94462,2012,A2 .

26
[ 394-69-4 ]
5-fluoroquinoline-8-sulfonyl chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
400 mg	With chlorosulfonic acid; at 0 - 130℃;	<strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (800 mg, 5.4 mmol) was added slowly to 10 mL of chlorosulfonic acid at 0°C. When the addition was complete, the reaction mixture was heated at 130°C overnight. The solution was allowed to cool and was slowly poured over ice. The aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried and evaporated to give the crude product, which was purified by column chromatography (5percent EtOAc/PE) to afford 400 mg of title compound. 1H NMR (CHLOROFORM-d) delta: 7.40 (t, J = 8.46 Hz, 1 H), 7.74 (dd, J = 8.60, 4.30 Hz, 1 H), 8.55 - 8.64 (m, 2 H), 9.32 (dd, J = 4.30, 1.88 Hz, 1 H). LC-MS: m/z 4 246 (M+H)+
400 mg	With chlorosulfonic acid; at 0 - 130℃;	<strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (800 mg, 5.4 mmol) was added slowly to 10 mL of chlorosulfonic acid at 0° C. When the addition was complete, the reaction mixture was heated at 130° C. overnight. The solution was allowed to cool and was slowly poured over ice. The aqueous layer was extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried and evaporated to give the crude product, which was purified by column chromatography (5percent EtOAc/PE) to afford 400 mg of title compound. 1H NMR (CHLOROFORM-d) delta: 7.40 (t, J=8.46 Hz, 1H), 7.74 (dd, J=8.60, 4.30 Hz, 1H), 8.55-8.64 (m, 2H), 9.32 (dd, J=4.30, 1.88 Hz, 1H). LC-MS: m/z 4 246 (M+H)+
400 mg	With chlorosulfonic acid; at 0 - 130℃;	<strong>[394-69-4]5-fluoro<strong>[394-69-4]quinoline</strong></strong> (800 mg, 5.4 mmol) was added slowly to 10 mL of chlorosulfonic acid at 0°C. When the addition was complete, the reaction mixture was heated at 130°C overnight. The solution was allowed to cool and was slowly poured over ice. The aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic extracts were dried and evaporated to give the crude product, which was purified by column chromatography (5percent EtOAc/PE) to afford 400 mg of title compound. 1H NMR (CHLOROFORM-d) delta: 7.40 (t, J = 8.46 Hz, 1 H), 7.74 (dd, J = 8.60, 4.30 Hz, 1 H), 8.55 - 8.64 (m, 2 H), 9.32 (dd, J = 4.30, 1.88 Hz, 1 H). LC-MS: m/z 4 246 (M+H)+

References: [1]Patent: WO2014/139144,2014,A1 .Location in patent: Page/Page column 179; 180.
[2]Patent: US2014/288081,2014,A1 .Location in patent: Paragraph 0740; 0741.
[3]Patent: WO2014/139325,2014,A1 .Location in patent: Page/Page column 192; 193.

27
[ 394-69-4 ]
[ 2292-84-4 ]
7-fluoro-4a-hydro-4,4-dimethyl-3H-benzo[c]quinolizin-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 24℃; for 0.333333h;	General procedure: To a stirred solution of 5-nitro<strong>[394-69-4]quinoline</strong> (8a, 103 mg, 0.59 mmol) and 2,2-dimethyl-3-ethoxycyclobutanone (7a, 92.5 mg, 0.65 mmol) in dry acetonitrile (2 mL) was addedMe3SiOTf (0.12 mL, 0.65 mmol) at 24 °C and the mixture was stirred for 20 min at the sametemperature. The reaction was quenched by adding aqueous solution of potassium sodium(+)-tartrate and the resulting mixture was extracted with ethyl acetate (three times). The combinedorganic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, andconcentrated. The crude product was purified by column chromatography on silica gel (13.7 g,hexane/ethyl acetate = 3:1 to 1:1) to afford 9a (101.4 mg, 0.375 mmol, 64percent).

References: [1]Tetrahedron Letters,2016,vol. 57,p. 3050 - 3052.

28
[ 394-69-4 ]
4-cyano-N-(5-fluoro-1-methyl-2-oxo-1,2-dihydroquinolin-6-yl)benzenesulfonamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 6998 - 7011.

29
[ 394-69-4 ]
[ 643752-95-8 ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 6998 - 7011.

30
[ 394-69-4 ]
5-fluoro-1-methylquinolin-2(1H)-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 6998 - 7011.

31
[ 394-69-4 ]
5-fluoro-1-methyl-6-nitroquinolin-2(1H)-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 6998 - 7011.

32
[ 394-69-4 ]
5-fluoro-1-methyl-6-aminoquinolin-2(1H)-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 6998 - 7011.

Historical Records

Technical Information

• Alkyl Halide Occurrence

Related Functional Groups of
[ 394-69-4 ]

Fluorinated Building Blocks

A131101 [396-30-5]

6-Fluoroquinoline

Similarity: 0.89

A107285 [1128-61-6]

6-Fluoro-2-methylquinoline

Similarity: 0.85

A609502 [325-14-4]

7-(Trifluoromethyl)quinoline

Similarity: 0.80

A614671 [1229037-03-9]

4-Chloro-5-fluoroquinoline

Similarity: 0.79

A125471 [394-68-3]

8-Fluoroquinoline

Similarity: 0.74

Related Parent Nucleus of
[ 394-69-4 ]

Quinolines

A131101 [396-30-5]

6-Fluoroquinoline

Similarity: 0.89

A107285 [1128-61-6]

6-Fluoro-2-methylquinoline

Similarity: 0.85

A609502 [325-14-4]

7-(Trifluoromethyl)quinoline

Similarity: 0.80

A614671 [1229037-03-9]

4-Chloro-5-fluoroquinoline

Similarity: 0.79

A125471 [394-68-3]

8-Fluoroquinoline

Similarity: 0.74

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
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P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 394-69-4

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