[ CAS No. 289656-45-7 ] {[proInfo.proName]}

Name: 289656-45-7|2,2-Bis(4-fluorophenyl)-2-phenylacetamide|98%
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SKU: A239412
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Quality Control of [ 289656-45-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 289656-45-7 ]

SDS Specification

Alternatived Products of [ 289656-45-7 ]

Product Details of [ 289656-45-7 ]

CAS No. :	289656-45-7	MDL No. :	MFCD09027349
Formula :	C₂₀H₁₅F₂NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SCTZUZTYRMOMKT-UHFFFAOYSA-N
M.W :	323.34	Pubchem ID :	216327
Synonyms :	ICA-17043	Chemical Name :	2,2-Bis(4-fluorophenyl)-2-phenylacetamide

Calculated chemistry of [ 289656-45-7 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	18
Fraction Csp3 :	0.05
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	87.9
TPSA :	43.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.35 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.79
Log Po/w (XLOGP3) :	4.11
Log Po/w (WLOGP) :	4.62
Log Po/w (MLOGP) :	4.72
Log Po/w (SILICOS-IT) :	4.88
Consensus Log Po/w :	4.22

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.72
Solubility :	0.00609 mg/ml ; 0.0000188 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.72
Solubility :	0.00615 mg/ml ; 0.000019 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-7.61
Solubility :	0.00000803 mg/ml ; 0.0000000248 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.44

Safety of [ 289656-45-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 289656-45-7 ]

* 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.

Upstream synthesis route of [ 289656-45-7 ]
Downstream synthetic route of [ 289656-45-7 ]

[ 289656-45-7 ] Synthesis Path-Upstream 1~8

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Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 8, p. 1385 - 1392

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Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 8, p. 1385 - 1392

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Reference： [1] Organic Process Research and Development, 2012, vol. 16, # 8, p. 1385 - 1392

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[ 289656-45-7 ] Synthesis Path-Downstream 1~15

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[ 420-37-1 ]
[ 905600-84-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 6 Preparation of 9 6.1 General Method A mixture of 1.0 mmol of 8 and an excess of trimethyloxonium tetrafluoroborate in 20 mL of anhydrous dichloromethane was stirred overnight at rt before quenched with triethyl amine. The resulting mixture was diluted with 50 mL of dichloromethane, washed with saturated NaCl, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 0.9 mmol of 9.; 6.2 Results Analytical data for an exemplary compound of the structure 9 is provided below.; 6.2.a 2,2-Bis-(4-fluoro-phenyl)-2-phenyl-acetimidic acid methyl ester 1H NMR (300 MHz, CDCl3) delta 7.32-7.30 (m, 3H), 7.13-7.09 (m, 6H), 6.99 (t, J=8.2 Hz, 4H), 3.83 (s, 3H); MS m/z: 338 (M+1).

Reference： [1]Patent: US2006/178346,2006,A1 .Location in patent: Page/Page column 26; 30

Yield	Reaction Conditions	Operation in experiment
		1.6 Compound Characterization by 1H and 19F NMR Spectroscopy and Melting Point The compounds of the invention were characterized by a combination of 1H and 19F NMR spectroscopy and the compound melting points were determined. 1: 1NMR Gamma(CHCl3): 7.39-7.26 (8H, m), 7.15-6.90 (5H, m), 5.83 (1H, brs), 5.72 (1H, brs); 19F NMR Gamma(CHCl3): -103.4 (1F, s), -115.8 (1F, s); m.p 180-181 C. 2: 1H NMR Gamma(CHCl3): 7.37-7.28 (6H, m), 7.15-7.05 (2H, m), 6.93 (1H, dt, J=8 and 2 Hz), 5.90 (1H, brs), 5.68 (1H, brs); 19F NMR Gamma(CHCl3): -103.4 (1F, m); m.p 210 C. 3: 1H NMR Gamma(CHCl3): 7.37-7.20 (9H, m), 7.04-6.91 (4H, m), 5.81 (1H, brs), 5.71 (1H, brs); 19F NMR Gamma(CHCl3): -115.7 (2F, s); m.p 180-181 C. 4: 1H NMR Gamma(CHCl3): 7.37-7.24 (12H, m), 6.97 (2H, t, J=8.5 Hz), 5.83 (1H, brs), 5.75 (1H, brs); 19F NMR Gamma(CHCl3): -116.2 (1F, s); m.p 193-194 C.

Yield	Reaction Conditions	Operation in experiment
58%		1.3 Preparation of Compound 3 Compound 3 was prepared in three steps from commercially available precursors in 58% yield.

4
bis(4-fluorophenyl)phenylacetonitrile [ No CAS ]
[ 289656-45-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfuric acid; acetic acid; at 25 - 130℃; for 3.0h;	A solution of concentrated sulfuric acid (50 mL) and glacial acetic acid (50 mL) was added to bis(4-fluorophenyl)phenylacetonitrile (18.9 g, 0.06 mol) at rt. The resulting orange solution was stirred and heated at 130 0C for 3 h. The reaction was cooled to 0 0C, poured into ice water (150 mL) and neutralized with ammonium hydroxide. The organics were extracted with chloroform (3 X 100 mL), combined and washed with brine (2 X 50 mL). The organics were dried (Na2SO4) and concentrated under reduced pressure to afford a yellow-orange solid. The solid was stirred with hot hexane (100 ml) for 30 min and filtered. Crystallization from dichloromethane/hexane gave bis(4-fluorophenyl)phenylacetamide (3) as a white crystalline solid (16.9 g, 0.052 mol, 87%).
	With sulfuric acid; In hexane; acetic acid;	1.3c Synthesis of bis(4-fluorophenyl)phenylacetamide (3) A solution of concentrated sulfuric acid (50 mL) and glacial acetic acid (50 mL) was added to bis(4-fluorophenyl)phenylacetonitrile (18.9 g, 0.06 mol) at rt. The resulting orange solution was stirred and heated at 130 C. for 3 h. The reaction was cooled to 0 C., poured into ice water (150 mL) and neutralized with ammonium hydroxide. The organics were extracted with chloroform (3100 mL), combined and washed with brine (250 mL). The organics were dried (Na2SO4) and concentrated under reduced pressure to afford a yellow-orange solid. The solid was stirred with hot hexane (100 ml) for 30 min and filtered. Crystallization from dichloromethane/hexane gave bis(4-fluorophenyl)phenylacetamide (3) as a white crystalline solid (16.9 g, 0.052 mol, 87%).

Reference： [1]Patent: WO2007/75849,2007,A2 .Location in patent: Page/Page column 29
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 976 - 982
[3]Patent: US6288122,2001,B1
[4]Organic Process Research and Development,2012,vol. 16,p. 1385 - 1392

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