501420-63-9|2-(3-Bromo-4-fluorophenyl)acetonitrile| Ambeed

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Quality Control of [ 501420-63-9 ] Purity: 97% SDS Specification

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Product Details of [ 501420-63-9 ]

CAS No. :	501420-63-9
Formula :	C₈H₅BrFN
M.W :	214.03
SMILES Code :	N#CCC1=CC=C(F)C(Br)=C1
MDL No. :	MFCD08458154
InChI Key :	ORKCKZRBHXMWBO-UHFFFAOYSA-N
Pubchem ID :	20113897

Safety of [ 501420-63-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 501420-63-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	43.62
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	23.79 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.92
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	2.37
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.07
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.	2.94
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	3.22
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.7

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.0
Solubility	0.215 mg/ml ; 0.00101 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.	-2.51
Solubility	0.661 mg/ml ; 0.00309 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	-4.03
Solubility	0.0202 mg/ml ; 0.0000942 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.	-5.92 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)	1.57

Application In Synthesis of [ 501420-63-9 ]

* 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 [ 501420-63-9 ]

[ 501420-63-9 ] Synthesis Path-Downstream 1~35

1
[ 78239-71-1 ]
[ 143-33-9 ]
[ 501420-63-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	In dimethyl sulfoxide; for 18h;	A solution of 2-bromo-4-(bromomethyl)-1 -fluorobenzene (5.0 g, 18.7 mmol) in DMSO (80 ml_) was treated with sodium cyanide (1.16 g, 22.4 mmol) and <n="100"/>stirred for 18 hours. The reaction was poured into ethyl acetate and washed 4x with 5% sodium chloride. The organic layer was dried over magnesium sulfate, filtered, and concentrated to an oil. Purification by silica gel column chromatography provided the title compound as a light amber oil (3.6 g, 75%). LC/MS: 10% - 90% CH3CN:H20 gradient over 5 minutes: 2.57 min. ,214, 216 (M+H); 1H NMR (400 MHz, CHLOROFORM-c/) delta ppm 3.73 (s, 2 H) 7.15 (t, J=8.40 Hz, 1 H) 7.20 - 7.32 (m, 1 H) 7.56 (dd, J=6.25, 2.35 Hz, 1 H).

References: [1]Patent: WO2009/69044,2009,A1 .Location in patent: Page/Page column 97-98.

2
[ 501420-63-9 ]
[ 111-44-4 ]
[ 1159186-66-9 ]

Yield	Reaction Conditions	Operation in experiment
30%		A solution of <strong>[501420-63-9]2-<strong>[501420-63-9](3-bromo-4-fluorophenyl)acetonitrile</strong></strong> (300 mg, 1.40 mmol) in DMSO (5 ml_) was treated with sodium hydride (120 mg, 3.0 mmol) and stirred for 1 hour. The reaction was then treated with 2-chloroethyl ether (409 mg, 0.335 ml_, 2.8 mmol) and stirred for 2 hours. The reaction was quenched with acetic acid, poured into water, and extracted 3x with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to an oil. Purification by silica gel column chromatography provided the title compound as a light amber oil (240 mg, 30%). 1H NMR (400 MHz, CHLOROFORM-c/) delta ppm 2.05 - 2.15 (m, 4 H) 3.86 - 3.94 (m, 2 H) 4.07 - 4.11 (m, 1 H) 4.10 - 4.15 (m, 1 H) 7.19 (dd, J=8.70, 8.11 Hz, 1 H) 7.43 (ddd, J=8.60, 4.30, 2.54 Hz, 1 H) 7.68 (dd, J=6.25, 2.54 Hz, 1 H).

References: [1]Patent: WO2009/69044,2009,A1 .Location in patent: Page/Page column 98.

3
[ 501420-63-9 ]
[ 74-88-4 ]
[ 1239964-06-7 ]

Yield	Reaction Conditions	Operation in experiment
88%		To a stirred suspension of NaH (16.3 g, 406 mmol, 3 eq) in anhyd THF (100 mL) at 0 C was added dropwise a solution of <strong>[501420-63-9]2-<strong>[501420-63-9](3-bromo-4-fluorophenyl)acetonitrile</strong></strong> (29 g, 135 mmol) in anhyd THF (200 mL). After stirring lh, Mel (42.1 mL, 675 mmol, 5 eq) was added to the reaction mixture. After stirring 2h at 0 C, the reaction was allowed to warm to room temperature, quenched carefully with H20 and extracted with EtOAc. The combined extracts were washed with brine, dried over MgS04 and evaporated in vacuo to give 2-(3-bromo-4- fluorophenyl)-2-methylpropanenitrile (29 g, 88%). 1H NMR (400 MHz, CDC13) delta 7.66-7.64 (m, 1H), 7.44-7.40 (m, 1H), 7.15 (t, J=8.4 Hz, 1H), 1.72 (s, 6H).
88%		To a stirred suspension of NaH (16.3 g, 406 mmol, 3 eq) in anhyd THF (100 mL) at 0 0C was added dropwise a solution of <strong>[501420-63-9]2-<strong>[501420-63-9](3-bromo-4-fluorophenyl)acetonitrile</strong></strong> (29 g, 135 mmol) in anhyd THF (200 mL). After stirring Ih, MeI (42.1 mL, 675 mmol, 5 eq) was added to the reaction mixture. After stirring 2h at 0 0C, the reaction was allowed to warm to room temperature, quenched carefully with H2O and extracted with EtOAc. The combined extracts were washed with brine, dried over MgSO4 and evaporated in vacuo to give 2-(3-bromo-4- fluorophenyl)-2-methylpropanenitrile (29 g, 88%). 1H NMR (400 MHz, CDCl3) delta 7.66-7.64 (m, IH), 7.44-7.40 (m, IH), 7.15 (t, J=8.4 Hz, IH), 1.72 (s, 6H).

References: [1]Patent: WO2011/71565,2011,A1 .Location in patent: Page/Page column 159.
[2]Patent: WO2010/93845,2010,A1 .Location in patent: Page/Page column 147-148.

4
[ 773837-37-9 ]
[ 866862-23-9 ]
[ 501420-63-9 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 0 - 20℃; for 4h;	To a stirred solution of 3-bromo-4-fluorobenzyl methanesulfonate (60 g, 0.212 mol) in DMF (300 mL) at 0 C was added NaCN (31.1 g, 0.635 mol, 3 eq) portionwise. After stirring at room temperature 4 h, the reaction mixture was partitioned in EtOAc and water. The organic layer was dried over MgS04 and evaporated in vacuo. The residue was purified by column chromatography (Hex/EtOAc = 4: 1) to give 2-(3-bromo-4- fluorophenyl)acetonitrile (30 g, 3 step overall yield: 55%). 1H NMR (400 MHz, CDC13) delta 7.56-7.54 (m, 1H), 7.28-7.24 (m, 1H), 7.14 (t, J=4.4 Hz, 1H), 3.73 (s, 2H).
	In N,N-dimethyl-formamide; at 0 - 20℃;	To a stirred solution of 3-bromo-4-fluorobenzyl methanesulfonate (60 g, 0.212 mol) in DMF (300 mL) at 0 0C was added NaCN (31.1 g, 0.635 mol, 3 eq) portionwise. After stirring at room temperature 4 h, the reaction mixture was partitioned in EtOAc and water. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography (Hex/EtOAc = 4:1) to give 2-(3-bromo-4- fluorophenyl)acetonitrile (30 g, 3 step overall yield: 55%). 1H NMR (400 MHz, CDCl3) delta 7.56-7.54 (m, IH), 7.28-7.24 (m, IH), 7.14 (t, J=4.4 Hz, IH), 3.73 (s, 2H).

References: [1]Patent: WO2011/71565,2011,A1 .Location in patent: Page/Page column 159.
[2]Patent: WO2010/93845,2010,A1 .Location in patent: Page/Page column 147-148.

5
[ 77771-02-9 ]
[ 501420-63-9 ]

References: [1]Patent: WO2011/71565,2011,A1 .
[2]Patent: WO2010/93845,2010,A1 .

6
[ 77771-03-0 ]
[ 501420-63-9 ]

References: [1]Patent: WO2011/71565,2011,A1 .
[2]Patent: WO2010/93845,2010,A1 .

7
[ 501420-63-9 ]
[ 874326-40-6 ]

Yield	Reaction Conditions	Operation in experiment
	With borane-THF; In tetrahydrofuran; methanol; at 0 - 20℃;Reflux;	a) 2- (3 -bromo-4-fluorophenyl)ethanamine To a stirred solution of <strong>[501420-63-9]2-(3-bromo-4-fluoro-phenyl)acetonitrile</strong> (5.0 g, 22.9 mmol, CAS501420-63-9) in THF (50 mL) was added borane-tetrahydronfuran complex 1.0 M in THF (45.8 mL, 45.8 mmol) at 0 C. The mixture was stirred at room temperature for 1 hour then heated to reflux overnight. The reaction mixture was then re-cooled to 0 C and MeOH (25 mL) was added. The mixture was heated to reflux for 90 min. The solvent was removed under vacuum and the residue was partitioned between EtOAc and aqueous 1.0 M HC1. The aqueous phase was made basic with aqueous 1.0 M NaOH then extracted with EtOAc. Organic layers were washed with saturated brine, dried (Na2S04) and concentrated in vacuo to afford the title compound (2.79 g, 56%) as viscous yellow oil which was used in the next step without further purification.

References: [1]Patent: WO2016/30306,2016,A1 .Location in patent: Page/Page column 28.

8
[ 501420-63-9 ]
N-(3-bromo-4-fluorophenethyl)-2-chloroacetamide [ No CAS ]