387-97-3|5-Fluoroquinolin-8-ol| Ambeed

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Quality Control of [ 387-97-3 ] Purity: 95% SDS Specification

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Product Details of [ 387-97-3 ]

CAS No. :	387-97-3
Formula :	C₉H₆FNO
M.W :	163.15
SMILES Code :	OC1=C2N=CC=CC2=C(F)C=C1
MDL No. :	MFCD00059754
InChI Key :	YHXLEKUJMPEQAJ-UHFFFAOYSA-N
Pubchem ID :	217907

Safety of [ 387-97-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 387-97-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	43.72
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.79
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	2.3
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.5
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.	1.61
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	2.38
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.12

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.92
Solubility	0.197 mg/ml ; 0.00121 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.	-2.63
Solubility	0.379 mg/ml ; 0.00233 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	-3.4
Solubility	0.0657 mg/ml ; 0.000403 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.	-5.66 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	1.0
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)	1.63

Application In Synthesis of [ 387-97-3 ]

* 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 [ 387-97-3 ]

[ 387-97-3 ] Synthesis Path-Downstream 1~40

1
[ 50-00-0 ]
[ 387-97-3 ]
[ 109-89-7 ]
[ 341-87-7 ]

References: [1]Journal of Organic Chemistry,1952,vol. 17,p. 229,230.
[2]Patent: DE944854,1952, .

2
[ 439-88-3 ]
[ 387-97-3 ]

References: [1]Journal of Organic Chemistry,1952,vol. 17,p. 229,230.

5
5-amino-quinolin-8-ol hydrochloride [ No CAS ]
[ 387-97-3 ]

References: [1]Chemistry and industry,1954,p. 344.

6
[ 394-33-2 ]
[ 56-81-5 ]
[ 387-97-3 ]

References: [1]Chemical Communications,2006,p. 1941 - 1943.

7
[ 1978-39-8 ]
[ 387-97-3 ]

References: [1]Journal of Organic Chemistry,1952,vol. 17,p. 229,230.

8
[ 445-83-0 ]
[ 387-97-3 ]

References: [1]Journal of Organic Chemistry,1952,vol. 17,p. 229,230.

9
[ 387-97-3 ]
[ 358-23-6 ]
[ 282547-44-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine; In dichloromethane; at 1 - 4℃; for 1h;Cooling with ice-water bath;	3.91 g (24 mmol) of 5-Fluoro-8-quinolinol and 24 ml of methylene chloride were added. The internal temperature was cooled to 4C in an ice-water bath, and then 4.3 ml (31 mmol) of triethylamine was added thereto. After the internal temperature descends down to 1C, 4.4 ml (26.4 mmol) of trifluoromethanesulfonic anhydride was added dropwise thereto. The reaction mixture varied to approximately black was stirred in the ice-water bath for 1 hour. After completion of the reaction, the reaction mixture was poured into water and the mixture was extracted with diethyl ether. The extract was washed with 1 mol/L (liter) of hydrochloric acid and water, and then the solvent was distilled off under reduced pressure by an evaporator to give a brown solid. The solid was dissolved in hot hexane (70C) and suction filtration was carried out to remove the insolubles. The filtrate was cooled to -78C to give 6.21 g of the desired compound as a brownish white solid (yield: 87%). 1H-NMR (300 MHz, CDCl3) delta: 7.20-7.28 (m, 1H), 7.55-7.63 (m, 2H), 8.47 (dd, 1H), 9.11 (dd, 1H) EI-MS (M/e): 295(M+), CI-MS (M/e): 296 (MH+)
	With triethylamine; In dichloromethane; at -15 - 0℃; for 1h;	To a cold solution (-15C) of 5-Fluoro,8-hydroxy-quinoline (2.5g) in 20 mL CH2Cl2, TEA is added (6.3 mL). To the cold mixture a solution of 6.5g of triflic anhydride in 10 mL of CH2Cl2, is added drop by drop with cooling. After complete addition, the reaction was stirred at 0C for 1 hour; The reaction was quenched with water, and the product was extracted with ether, dried and the solvent was removed to give 3.4g of product. MS (ES) m/z (relative intensity): 296 (M+H+,100).

References: [1]Patent: EP1847545,2007,A1 .Location in patent: Page/Page column 36.
[2]Patent: EP1147083,2004,B1 .Location in patent: Page 42.

10
[ 387-97-3 ]
⁽¹⁸⁾F-5-fluoro-8-hydroxyquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; [2.2.2]cryptande; In dimethyl sulfoxide; at 110 - 160℃; for 0 - 0.5h;	The radioactive fluoride [18F] is transferred to a 5 mL borosilicate reaction vial and is azeotropically dried with acetonitrile in the presence of 4.0 mg of K2CO3 and 14.6 mg of Kryptofix 2.2.2. The precursor fluoride derivative dissolved in 0.5 mL of DMSO is added to the vial containing the dry radioactive fluoride, the K2CO3 and the Kryptofix 2.2.2 and the isotope exchange reaction is performed heating to 110, 130 and 160 C. for 0-30 minutes to optimise the reaction. Purification of the radiofluorinated derivative is performed by reverse phase HPLC. The corresponding fractions are collected and concentrated under reduced pressure.
	With potassium carbonate; In dimethyl sulfoxide; at 110 - 160℃; for 0 - 0.5h;	The radioactive fluoride [18F] is transferred to a 5 mL borosilicate reaction vial and is azeotropically dried with acetonitrile in the presence of 4.0 mg of K2CO3 and 14.6 mg of Kryptofix 2.2.2. The precursor fluoride derivative dissolved in 0.5 mL of DMSO is added to the vial containing the dry radioactive fluoride, the K2CO3 and the Kryptofix 2.2.2 and the isotope exchange reaction is performed heating to 110, 130 and 160C for 0-30 minutes to optimise the reaction. Purification of the radiofluorinated derivative is performed by reverse phase HPLC. The corresponding fractions are collected and concentrated under reduced pressure.

References: [1]Patent: US2008/63599,2008,A1 .Location in patent: Page/Page column 8.
[2]Patent: EP1563852,2005,A1 .Location in patent: Page/Page column 13.

11
[ 387-97-3 ]
[ 1098595-19-7 ]

Yield	Reaction Conditions	Operation in experiment
		5-fluoroquinolin-8-yl trifluoroacetate The desired product was prepared by substituting <strong>[387-97-3]5-fluoro-8-hydroxyquinoline</strong> for vanillin in Example 122H.

References: [1]Patent: US2002/55631,2002,A1 .

12
[ 387-97-3 ]
5-fluoro-8-hydroxyquinoline-7-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In CO2;	Preparation 4 5-Fluoro-8-hydroxyquinoline-7-carboxylic acid (Formula A-2 wherein R1 is -F and R2 is -H) Refer to Chart A. 5-Fluoro-8-hydroxyquinoline (3.00 g) and potassium carbonate (7.62 g) are mixed together in a stainless steel bomb and heated to 170 C. under 800 p.s.i. CO2 for 7 days. The reaction is cooled and the resulting solid is partitioned between 800 mL water and 400 mL EtOAc in a separatory funnel. The aqueous layer is washed with EtOAc (3X 400 mL). The aqueous layer is then acidified to pH 4.5 with conc. HCl and cooled. The resulting solid is collected, washed with water and dried. The crude product is triturated with i-PrOH and dried to yield 1.67 g of the title product as a brown solid. Physical characteristics are as follows: MP 277-279 C. 1H NMR (300 MHz, DMSO) delta 9.01, 8.49, 7.79, 7.57. IR (mull) 2446, 2417, 1995, 1965, 1637, 1445, 1405, 1270, 1257, 1215, 1068, 1032, 819, 785, 742 cm-1. MS (EI) m/z 207 (M+), 207, 189, 163, 161, 135, 134, 133, 132, 107, 81. Anal. found: C, 57.95; H, 2.88; N, 6.66.

References: [1]Patent: US6211376,2001,B1 .

13
[ 387-97-3 ]
[ 205040-84-2 ]

Yield	Reaction Conditions	Operation in experiment
	In chlorosulfonic acid;	Preparation 29 5-fluoro-8-hydroxy-7-quinolinesulfonyl chloride (Formula S-2) A solution of <strong>[387-97-3]5-fluoro-8-hydroxyquinoline</strong> (0.50 g) in 4.0 mL of chlorosulfonic acid is stirred for 3 h at 90 C. and then 13 h at 105 C. The mixture is then cooled to 0 C. and poured onto 50 mL of finely divided -15 C. ice. The bright orange-red precipitate is collected by filtration, washed with four 10-mL portions of 0 C. distilled water and three 2 mL portions of diethyl ether, and dried in a stream of air to give 0.208 g of the title compound as a red-orange powder. Physical characteristics are as follows: MP 248-250 C. (decomposition); Anal. found: C, 41.01; H, 2.05; N, 5.32; S, 12.25.

References: [1]Patent: US6211376,2001,B1 .

14
nickel(II) sulphate [ No CAS ]
[ 387-97-3 ]
[ 98781-76-1 ]

References: [1]Journal of the Chemical Society A: Inorganic, Physical, Theoretical,1966,p. 73 - 76.

15
[ 387-97-3 ]
gallium(III) nitrate nonahydrate [ No CAS ]
fac-tris(5-fluoro-8-hydroxyquinolinato)gallium(III) complex [ No CAS ]
mer-tris(5-fluoro-8-hydroxyquinolinato)gallium(III) complex [ No CAS ]

References: [1]European Journal of Inorganic Chemistry,2000,p. 545 - 550.

16
[ 387-97-3 ]
[Os2(CO)6(μ-trifluoroacetate)2] [ No CAS ]
Os(CO)3(trifluoroacetate)(5-fluoro-8-quinolinolate) [ No CAS ]

References: [1]Inorganic Chemistry,2005,vol. 44,p. 4594 - 4603.

17
[ 387-97-3 ]
[ 555-31-7 ]
[ 158241-72-6 ]

References: [1]Chemical Communications,2006,p. 1941 - 1943.

18
[ 387-97-3 ]
[ 621-88-5 ]
[ 100-52-7 ]
N-[(5-fluoro-8-hydroxyquinolin-7-yl)(phenyl)methyl]-2-phenoxyacetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6454 - 6457.

19
[ 387-97-3 ]
[ 80937-33-3 ]
[ 7718-98-1 ]
[ 67-63-0 ]
[ 1166298-67-4 ]

References: [1]Inorganica Chimica Acta,2009,vol. 362,p. 3201 - 3207.

20
[ 387-97-3 ]
[ 109384-19-2 ]
[ 1189551-18-5 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at 20℃; for 20h;Inert atmosphere;	Intermediate 45 1,1-Dimethylethyl 4-[(5-fluoro-8-quinolinyl)oxy]-l-piperidinecarboxylate A stirring solution of <strong>[387-97-3]5-fluoro-8-quinolinol</strong> (commercially available, for example, from TCI) (1 g, 6.13 mmol), triphenylphosphine (1.608 g, 6.13 mmol) and ferf-butyl 4-hydroxy-i-piperidinecarboxylate (commercially available, for example, from Aldrich) (1.111 g, 5.52 mmol) in DCM (22 ml) was treated with diisopropyl azodicarboxylate (1.207 ml, 6.13 mmol) and the resulting mixture was stirred at ambient temperature under a nitrogen atmosphere for -20 h. The solvent was evaporated giving a residue that was purified on a Flashmaster Il using a silica cartridge (100 g) and a 5-50% EtOAc in cyclohexane gradient over 60 minutes. Evaporation of the solvent from appropriate fractions gave a crude sample of the title compound (453 mg). LCMS RT= 3.23 min, ES+ve m/z 347 [M+H]+.

References: [1]Patent: WO2010/94643,2010,A1 .Location in patent: Page/Page column 54-55.

21
[ 387-97-3 ]
[ 1312686-12-6 ]