259750-61-3|1-(4-Bromo-2-fluorophenyl)propan-1-one| Ambeed

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Quality Control of [ 259750-61-3 ] Purity: 95% SDS Specification

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Product Details of [ 259750-61-3 ]

CAS No. :	259750-61-3
Formula :	C₉H₈BrFO
M.W :	231.06
SMILES Code :	CCC(C1=CC=C(Br)C=C1F)=O
MDL No. :	MFCD11226830
Boiling Point :	No data available
InChI Key :	VAWRVSQLVIYZRK-UHFFFAOYSA-N
Pubchem ID :	18546218

Safety of [ 259750-61-3 ]

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

Computational Chemistry of [ 259750-61-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	49.1
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.41
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	2.87
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.6
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.	3.23
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	3.59
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.14

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.32
Solubility	0.111 mg/ml ; 0.00048 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.	-2.89
Solubility	0.299 mg/ml ; 0.00129 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	-4.28
Solubility	0.0122 mg/ml ; 0.0000528 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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.	-5.67 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)	1.45

Application In Synthesis of [ 259750-61-3 ]

* 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 [ 259750-61-3 ]

[ 259750-61-3 ] Synthesis Path-Downstream 1~35

1
[ 2386-64-3 ]
[ 801303-33-3 ]
[ 259750-61-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3983 - 3987.

2
[ 96-32-2 ]
[ 259750-61-3 ]
[ 644984-82-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3983 - 3987.

3
[ 112704-79-7 ]
[ 259750-61-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3983 - 3987.
[2]Patent: US2011/263559,2011,A1 .
[3]Patent: WO2017/81483,2017,A1 .

4
[ 259750-61-3 ]
6-[4-(2-benzyl-3-oxo-cyclohex-1-enylamino)-2-fluoro-phenyl]-5-methyl-4,5-dihydro-2H-pyridazin-3-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3983 - 3987.

5
[ 259750-61-3 ]
[ 644985-07-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3983 - 3987.

7
[ 7446-70-0 ]
[ 1073-06-9 ]
[ 79-03-8 ]
[ 259750-61-3 ]

Yield	Reaction Conditions	Operation in experiment
18%		4'-Bromo-2'-fluoropropiophenone A mixture of 3-fluorobromobenzene (5.0 g, 29 mmol) and aluminium (III) chloride (11.6 g, 87 mmol) was heated under argon until a slurry formed. Propionyl chloride (3.2 g, 35 mmol) was added over 15 min and the mixture was heated at 90 C. for 1 h. The reaction was poured onto ice-water (100 mL) and the resultant mixture was extracted with dichloromethane (3*50 mL). The combined organic extracts were dried (magnesium sulfate), concentrated in vacuo and purified by column chromatography (SiO2; heptane) to give the product (1.2 g, 18%) as a colourless oil: NMR deltaH (400 MHz, CDCl3) 1.18 (3H, t, J 7.5), 2.95 (2H, m), 7.29-7.38 (2H, m) and 7.75 (1H, t, J 8 Hz).

References: [1]Patent: US6552062,2003,B1 .

8
[ 1214900-59-0 ]
[ 259750-61-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20℃; for 12.0h;	Intermediate 100 1-(4-bromo-2-fluorophenyl)propan-1-one To a solution of intermediate 99 (5.8 g, 24.89 mmoles) in DMF (30 ml), pyridinium dichromate (14.04 g, 37.33 mmoles) was added at room temperature. After 12 h, the reaction mixture was quenched with water, diluted with ethyl acetate and filtered through celite. The organic layer was washed with brine solution and dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as colourless liquid (4.4 g, 76% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 7.78 (t, J=8.1 Hz, 1H), 7.38 (m, 2H), 2.55 (m, 2H), 1.21 (t, J=7.1 Hz, 3H).
1.84 g	With manganese(IV) oxide; In 1,4-dioxane; at 80℃; for 16.0h;	To a solution of the compound [140-1] obtained in the process (1) (3.78 g) in 1,4-dioxane (50 mL) was added manganese dioxide (10.6 g) at room temperature, and then the reaction mixture was stirred at 80C for 16 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (1.84 g) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 7.77 (1H, t, J = 8.2 Hz), 7.40-7.30 (2H, m), 3.02-2.94 (2H, m), 1.20 (3H, t, J = 7.2 Hz).

References: [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 3703 - 3726.
[2]Patent: US2011/118257,2011,A1 .Location in patent: Page/Page column 98.
[3]Patent: EP2669270,2013,A1 .Location in patent: Paragraph 0816-0817.
[4]Journal of Medicinal Chemistry,2019,vol. 62,p. 342 - 358.

9
[ 57848-46-1 ]
[ 259750-61-3 ]

References: [1]Patent: US2011/118257,2011,A1 .
[2]Patent: EP2669270,2013,A1 .
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 3703 - 3726.
[4]Journal of Medicinal Chemistry,2019,vol. 62,p. 342 - 358.

10
[ 259750-61-3 ]
[ 199172-01-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With hydrazine hydrate; In dimethyl sulfoxide; at 130℃; for 22.0h;	Intermediate 101 6-bromo-3-ethyl-1H-indazole To a solution of intermediate 100 (4.3 g, 18.53 mmoles) in DMSO (4.5 ml), hydrazine hydrate 17.3 ml, 357.7 mmoles) was added at room temperature and heated to 130 C. After 22 h, the reaction mixture cooled to room temperature, quenched with water and solid precipitated was filtered and dried under vacuum to afford the title compound as colourless solid (3.8 g, 91% yield). 1H-NMR (delta ppm, DMSO-d6, 400 MHz): delta 12.73 (s, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.66 (d, J=1.1 Hz, 1H), 7.18 (dd, J=8.5, 1.5 Hz, 1H), 2.92 (q, J=7.6 Hz, 2H), 1.30 (t, J=7.6 Hz, 3H).
0.95 g	With hydrazine hydrate; In 1,4-dioxane; at 110℃; for 17.0h;	To a solution of the compound [140-2] obtained in the process (2) (1.84 g) in 1,4-dioxane (20 mL) was added hydrazine monohydrate (1.2 mL) at room temperature, and the reaction mixture was stirred at 110C for 17 hours. To the reaction mixture was added 0.1N-hydrochloric acid, and then extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (0.95 g) as a white solid. 1H-NMR (400 MHz, CDCl3) delta: 10.50-9.50 (1H, br), 7.61 (1H, s), 7.57 (1H, d, J = 8.5 Hz), 7.28-7.21 (1H, m), 3.00 (2H, q, J = 7.6 Hz), 1.41 (3H, t, J = 7.6 Hz).

References: [1]Patent: US2011/118257,2011,A1 .Location in patent: Page/Page column 98.
[2]Patent: EP2669270,2013,A1 .Location in patent: Paragraph 0818-0819.

11
[ 259750-61-3 ]
[ 1300585-17-4 ]

References: [1]Patent: US2011/118257,2011,A1 .

12
[ 259750-61-3 ]
[ 1300582-48-2 ]

References: [1]Patent: US2011/118257,2011,A1 .

13
[ 259750-61-3 ]
[ 1300582-50-6 ]

References: [1]Patent: US2011/118257,2011,A1 .

14
[ 100-63-0 ]
[ 259750-61-3 ]
[ 1332527-10-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With toluene-4-sulfonic acid; In water; for 1.0h;Reflux;	Into a 1000-mL round-bottom flask, was placed a solution of <strong>[259750-61-3]1-(4-bromo-2-fluorophenyl)propan-1-one</strong> (32 g, 138.53 mmol, 1.00 equiv) in ethanol (300 mL), 1-phenylhydrazine (15.0 g, 138.89 mmol, 1.00 equiv), TSA-H2O (1.32 g, 6.95 mmol, 0.05 equiv). The resulting solution was heated to reflux for 1 h in an oil bath. The resulting mixture was concentrated under vacuum to yield 1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine as a yellow solid (44.3 g, yield: 99%).
	toluene-4-sulfonic acid; In ethanol; for 1.0h;Reflux;	Into a 1000-mL round-bottom flask, was placed a solution of <strong>[259750-61-3]1-(4-bromo-2-fluorophenyl)propan-1-one</strong> (32 g, 138.53 mmol, 1.00 equiv) in ethanol (300 mL), 1-phenylhydrazine (15.0 g, 138.89 mmol, 1.00 equiv), TSA-H2O (1.32 g, 6.95 mmol, 0.05 equiv). The resulting solution was heated to reflux for 1 h in an oil bath. The resulting mixture was concentrated under vacuum to yield (Z)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine and (E)-1-(1-(4-bromo-2-fluorophenyl)propylidene)-2-phenylhydrazine as a yellow solid. MS: 322 (MH+)

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4762 - 4767.
[2]Patent: US2011/263559,2011,A1 .Location in patent: Page/Page column 30.

15
[ 259750-61-3 ]
[ 1332527-13-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 4762 - 4767.
[2]Patent: US2011/263559,2011,A1 .

16
[ 259750-61-3 ]
C₂₄H₃₀N₄O₂ [ No CAS ]