24410-59-1|5-Fluorobenzofuran| Ambeed

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Quality Control of [ 24410-59-1 ] Purity: 95% SDS Specification

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Product Details of [ 24410-59-1 ]

CAS No. :	24410-59-1
Formula :	C₈H₅FO
M.W :	136.12
SMILES Code :	FC1=CC2=C(OC=C2)C=C1
MDL No. :	MFCD08236757
InChI Key :	FTVHMXRCGNWCOL-UHFFFAOYSA-N
Pubchem ID :	11788322

Safety of [ 24410-59-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 24410-59-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	36.17
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	13.14 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.02
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	2.43
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.99
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.	2.0
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	2.87
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.46

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.88
Solubility	0.179 mg/ml ; 0.00132 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.	-2.35
Solubility	0.61 mg/ml ; 0.00448 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	-3.53
Solubility	0.0398 mg/ml ; 0.000292 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.	-5.41 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)	2.22

Application In Synthesis of [ 24410-59-1 ]

* 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 [ 24410-59-1 ]

[ 24410-59-1 ] Synthesis Path-Downstream 1~41

2
[ 59769-37-8 ]
[ 24410-59-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	With tin-exchanged H-b zeolite (Sn-b); for 1.5h;Reflux;	General procedure: A 25 mL round-bottomed flask was charged with 2-aryloxyacetaldehyde diethyl acetals (1 mmol), Sn-b (0.1 g), andtrifluorotoluene (10 mL). The mixture was stirred under refluxingcondition and monitored by GC. Upon completion, the mixture wascooled to room temperature, and the catalyst Sn-b was filtrate off.The filter cake was washed with trifluorotoluene (10 mL3). Thecombined filtratewas concentrated under vacuum. The residuewaspurified by flash column chromatography on SiO2 (petroleumether/ethyl acetate) to afford the desired 2,3-unsubstituted benzo[b]furans.
45%	With PPA; In benzene; for 2.5h;Heating / reflux;	To a mixture of benzene (200 ml) containing polyphosphoric acid (7.9 g, 0.035 mol) was added 2-(4-fluoro-phenoxy)-acetaldehyde diethyl acetal (8 g, 0.035 mol). The mixture was stirred vigorously while being heated to reflux for 2.5 hours. The reaction mixture was cooled to room temperature and decanted from the polyphosphoric acid. The solvent was removed under vacuum. Chromatography (5% ethyl acetate-hexanes) afforded 3.4 g (45%) of product as a clear oil: 1H NMR (CDCl3) delta 6.74 (dd, 1H, J = 2.0, 0.6 Hz), 7.01 (td, 1H, J = 9, 2.7 Hz), 7.25 (dd, 1H, J = 8.4, 2.7 Hz), 7.43 ( dd, 1H, J = 9, 3.9 Hz), 7.65 (d, 1H, J = 1.8 Hz).
	With amberlyst 15; In hexane; at 20 - 200℃; for 11h;	To a solution of 16.0 g of 1-(2,2-diethoxyethoxy)-4-fluorobenzene in 50 ml n-hexane was added 3.2 g of amberlyst 15 at room temperature. After the mixture was treated in a sealed tube at 200C for 11 hours, the amberlyst 15 was filtered off. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (n-hexane), to give 4.8 g of the title compound as a colorless oil.1H-NMR (400 MHz, CDCl3) d 6.74 (1H, dd, J = 1.2, 2.4 Hz), 7.02 (1H, dt, J = 2.4, 8.8 Hz), 7.25 (1H, dd, J = 2.4, 8.8 Hz), 7.41 - 7.44 (1H, m), 7.65 (1H, d, J = 2.4 Hz).

	Amberlyst 15; In toluene; at 120℃;Reflux;	EXAMPLE 6Preparation of 5-substituted benzofuranThe l-substituted-4-(2,2-diethoxyethoxy)benzene (100 mmol) was refluxed in dry toluene (30 ml) with Amberlyst 15 (2.5 g) at 120C for 6-8 h with concomitant removal of the azeotrope using a Dean-Stark apparatus. The resulting reaction mixture was filtered and the resin was washed with an excess of toluene. The combined filtrates were concentrated to dryness under reduced pressure and the resulting compounds were purified by crystallization, by distillation or by silica gel column chromatography. The following 5-substituted benzofurans were prepared by described above method: 5-Fluorobenzofuran, oil
	With polyphosphoric acid; In benzene; for 2.5h;Reflux;	Step 2. 5-Fluorobenzofuran To a mixture of benzene (200 mL) containing polyphosphoric acid (80 g, 236.69 mmol) was added 2-(4-fluoro-phenoxy)-acetaldehyde diethyl acetal (45 g, 197.37 mmol). The mixture was stirred vigorously while being heated to reflux for 2.5 hours. The reaction mixture was cooled to room temperature and decanted from the polyphosphoric acid. The solvent was removed under vacuum to give the residue, which was purified by a silica gel column (1% ethyl acetate in petroleum ether) to afford 5-fluorobenzofuran as colorless oil (14.0 g, crude).1H-NMR (300 MHz, CDCl3): delta 7.67 (d, J=2.1 Hz, 1H), 7.44-7.48 (m, 1H), 7.27-7.30 (m, 1H), 7.01-7.08 (m, 1H), 6.76-6.77 (m, 1H)
	With polyphosphoric acid; In benzene; for 2.5h;Reflux;	Step 2. 5-FluorobenzofuranTo a mixture of benzene (200 mL) containing polyphosphoric acid (80 g, 236.69 mmol) was added 2-(4-fluoro-phenoxy)-acetaldehyde diethyl acetal (45 g, 197.37 mmol). The mixture was stirred vigorously while being heated to reflux for 2.5 hours. The reaction mixture was cooled to room temperature and decanted from the polyphosphoric acid. The solvent was removed under vacuum to give the residue, which was purified by a silica gel column with 1% ethyl acetate in petroleum ether to afford 5-fluorobenzofuran as colorless oil (14.0 g, crude). 'H-NMR (300 MHz, CDCI3): delta 7.67 (d, / = 2.1 Hz, 1H), 7.44 - 7.48 (m, 1H), 7.27 - 7.30 (m, 1H), 7.01- 7.08 (m, 1H), 6.76 - 6.77 (m, 1H)

References: [1]Tetrahedron,2015,vol. 71,p. 4835 - 4841.
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.
[3]Patent: EP1147083,2004,B1 .Location in patent: Page 35.
[4]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276.
[5]European Journal of Organic Chemistry,2016,vol. 2016,p. 2268 - 2273.
[6]Journal of Medicinal Chemistry,2004,vol. 47,p. 1609 - 1612.
[7]Patent: EP1380576,2004,A1 .Location in patent: Page 66.
[8]Patent: WO2011/99010,2011,A1 .Location in patent: Page/Page column 38.
[9]Patent: US2012/225863,2012,A1 .Location in patent: Page/Page column 17.
[10]Patent: WO2012/119046,2012,A2 .Location in patent: Page/Page column 65-66.
[11]New Journal of Chemistry,2016,vol. 40,p. 6564 - 6567.
[12]Angewandte Chemie - International Edition,2019,vol. 58,p. 10148 - 10152.
Angew. Chem.,2019,vol. 131,p. 10254 - 10258,5.

3
[ 24410-59-1 ]
[ 75-07-0 ]
1-(5-fluoro-benzofuran-2-yl)-ethanol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1609 - 1612.

4
[ 24410-59-1 ]
[ 245762-35-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogen;palladium 10% on activated carbon; In acetic acid; under 2585.81 Torr; for 12h;	A solution of <strong>[24410-59-1]5-fluorobenzofuran</strong> and 10% palladium on carbon in acetic acid (25 ml) was hydrogenated under 50 psi for 12 hours. The catalyst was filtered through celite and the celite was washed with methylene chloride (200 ml). The organic layer was washed sequentially with 1N NaOH (3 x 100 ml), brine (3 x 100 ml) and dried over anhydrous sodium sulfate and filtered. The solvent was removed under vacuum to afforded 2.59 g (85%) of product as a clear oil: 1H NMR (300 MHz, CDCl3): delta 3.12 (t, 2H, J = 8.7 Hz), 4.58 (t, 2H, J = 8.7 Hz), 6.68 (dd, 1H, J = 8.7, 4.2 Hz), 6.79 (tm, 1H, J = 8.7 Hz), 6.89 (dm, 1H, J = 8.1 Hz).

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.
[2]Patent: EP1147083,2004,B1 .Location in patent: Page 35.

5
[ 24410-59-1 ]
[ 245762-36-1 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.

6
[ 24410-59-1 ]
[ 245762-37-2 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.

7
[ 24410-59-1 ]
[ 245762-38-3 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.

8
[ 24410-59-1 ]
[ 245762-40-7 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.

9
[ 24410-59-1 ]
[ 245762-39-4 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.

10
[ 24410-59-1 ]
[2-(5-Fluoro-2,3-dihydro-benzofuran-7-yloxy)-ethyl]-[2-(5-fluoro-1H-indol-3-yl)-ethyl]-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.

11
[ 371-41-5 ]
[ 24410-59-1 ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842.
[2]Journal of Medicinal Chemistry,2004,vol. 47,p. 1609 - 1612.
[3]Patent: US2012/225863,2012,A1 .
[4]Patent: WO2012/119046,2012,A2 .
[5]Patent: WO2015/42397,2015,A1 .
[6]Tetrahedron,2015,vol. 71,p. 4835 - 4841.
[7]European Journal of Organic Chemistry,2016,vol. 2016,p. 2268 - 2273.
[8]New Journal of Chemistry,2016,vol. 40,p. 6564 - 6567.
[9]Journal of the American Chemical Society,2017,vol. 139,p. 8267 - 8276.
[10]Angewandte Chemie - International Edition,2019,vol. 58,p. 10148 - 10152.
Angew. Chem.,2019,vol. 131,p. 10254 - 10258,5.

12
[ 24410-59-1 ]
1-(5-fluorobenzofuran-2-yl)ethan-1-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1609 - 1612.

13
[ 24410-59-1 ]
5-fluoro-2-(5-fluoro-benzofuran-2-yl)-1<i>H</i>-indole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 1609 - 1612.

14
[ 24410-59-1 ]
[ 150-46-9 ]
[ 473416-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20℃; for 3.33333h;	In a nitrogen atmosphere, to a solution of 2.0 g of <strong>[24410-59-1]5-fluorobenzofuran</strong> in 150 ml tetrahydrofuran was added 18.5 ml of a 1.59 M solution of n-butyllithium in n-hexane at-78C, and the mixture was stirred at the same temperature for 10 minutes and at 0C for further 10 minutes. At -78C, 3.7 ml of triethoxyborane was added, and the mixture was stirred for 2 hours while elevating to 0C. 30 ml of 1 N hydrochloric acid was added, stirred at room temperature for 1 hour, and then the mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane = 1:3 to 1:1), to give 525 mg of the title compound as colorless crystals.1H-NMR (400 MHz, CDCl3) d 7.09 (1H, dt, J = 2.4, 8.8 Hz), 7.29 (1H, dd, J = 2.4, 8.8 Hz), 7.33 (1H, s), 7.44 (1H, dd, J = 4.0, 8.8 Hz).

References: [1]Patent: EP1380576,2004,A1 .Location in patent: Page 67.

15
[ 24410-59-1 ]
[ 1461-22-9 ]
[ 684221-16-7 ]

Yield	Reaction Conditions	Operation in experiment
		Butyllithium (1.5 mL, 2.4 mmol, 1.6 M) was added at -75 C. to a solution of <strong>[24410-59-1]5-fluorobenzofuran</strong> (0.3 g, 2.2 mmol) in THF (10 mL). Tributyltin chloride (0.98 g, 1 mL) was added at -75 C. and the mixture was allowed to warm to 25 C. over a period of 2 hours. Water (25 mL) was added and the aqueous layer was extracted with diethyl ether (2×25 mL). The combined organic extracts were dried over Na2SO4 and concentrated. Silica gel chromatography (pentane) provided tributyl-(<strong>[24410-59-1]5-fluorobenzofuran</strong>-2-yl)-stannane (210 mg).

References: [1]Patent: US2004/87601,2004,A1 .Location in patent: Page 24.

16
[ 24410-59-1 ]
[ 1461-22-9 ]
tributyl-(5-fluorobenzofuran-2-yl)-stannane [ No CAS ]

References: [1]Patent: US2004/87601,2004,A1 .Location in patent: Page 23.

17
[ 24410-59-1 ]
[ 1268864-98-7 ]

References: [1]Patent: US2012/225863,2012,A1 .
[2]Patent: WO2012/119046,2012,A2 .

18
[ 24410-59-1 ]
[ 1394971-30-2 ]

References: [1]Patent: US2012/225863,2012,A1 .
[2]Patent: WO2012/119046,2012,A2 .

19
[ 24410-59-1 ]
[ 1396752-49-0 ]