656-35-9|2-(2,4-Difluorophenyl)acetonitrile| Ambeed

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Quality Control of [ 656-35-9 ] Purity: 97% SDS Specification

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Product Details of [ 656-35-9 ]

CAS No. :	656-35-9
Formula :	C₈H₅F₂N
M.W :	153.13
SMILES Code :	N#CCC1=CC=C(F)C=C1F
MDL No. :	MFCD00009971
InChI Key :	AGAOESUOSOGZOD-UHFFFAOYSA-N
Pubchem ID :	69565

Safety of [ 656-35-9 ]

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

Computational Chemistry of [ 656-35-9 ] 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	3.0
Num. H-bond donors	0.0
Molar Refractivity	35.88
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.	1.71
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	1.78
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.87
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.	2.63
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	2.96
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.39

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.25
Solubility	0.864 mg/ml ; 0.00564 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.	-1.9
Solubility	1.94 mg/ml ; 0.0127 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-3.43
Solubility	0.0569 mg/ml ; 0.000372 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.	-5.97 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)	1.39

Application In Synthesis of [ 656-35-9 ]

* 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 [ 656-35-9 ]

[ 656-35-9 ] Synthesis Path-Downstream 1~35

1
[ 452-76-6 ]
[ 656-35-9 ]

References: [1]Ind. chim. belge Sonderband 31. Congr. int. chim. ind. Luettich 1958 Bd. 2, S. 466,.
[2]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 312 - 322.

2
[ 656-35-9 ]
[ 399-34-8 ]

References: [1]Ind. chim. belge Sonderband 31. Congr. int. chim. ind. Luettich 1958 Bd. 2, S. 466,.

3
[ 452-07-3 ]
[ 143-33-9 ]
[ 656-35-9 ]

References: [1]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 312 - 322.

4
[ 656-35-9 ]
[ 100-52-7 ]
[ 2647-30-5 ]

References: [1]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 312 - 322.

5
[ 656-35-9 ]
[ 100-10-7 ]
[ 1525-45-7 ]

References: [1]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 312 - 322.

6
[ 656-35-9 ]
[ 138-89-6 ]
[ 966-98-3 ]

References: [1]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 312 - 322.

7
[ 656-35-9 ]
2-(2,4-difluorophenyl)-acetamidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 4 Preparation of 1-TDHIA-2,4A,8-TRIAZA-CYCLOPENTA[B]NAPHTHALENE-DIONES
	With hydrogenchloride; ammonia; In ethanol;	Step 1. 2-(2,4-Difluorophenyl)-acetamidine hydrochloride Into a solution of 49.44 g (0.323 mol) of <strong>[656-35-9]2,4-difluorophenylacetonitrile</strong> (commercially available) in 20.8 mL (0.354 mol) of ethanol cooled to 0 C. in an ice bath and stirred under a dry N2 atmosphere was added 14.61 g (0.400 mol) of gaseous HCl. After 20 min the reaction mixture solidified, this was then allowed to warm to room temperature and held at this temperature for 72 hours. To the mixture was then added 140 mL of ethanol, followed by 150 mL (0.42 mol) of 4.2M ammonia in ethanol. This mixture was stirred for an additional 3 hours at room temperature and filtered. The solvent was removed from the filtrate by evaporation to afford 65.7 g of the title compound as a white solid, mp 163-164 C. NMR: (DMSO-d6) d 3.72 (s, 2H), 7.16 (m, 1H), 7.33 (m, 1H), 7.50 (m, 1H), 8.95 (broad, 4H). This compound was taken directly to the next step.

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3070 - 3088.
[2]Patent: US2006/173026,2006,A1 .Location in patent: Page/Page column 20.
[3]Patent: US5580872,1996,A .

8
[ 108-73-6 ]
[ 656-35-9 ]
2-(2,4-Difluoro-phenyl)-1-(2,4,6-trihydroxy-phenyl)-ethanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1323 - 1326.

10
[ 656-35-9 ]
[ 118753-70-1 ]
[ 216311-12-5 ]

Yield	Reaction Conditions	Operation in experiment
0.720 g (62%)	With NaH; In N,N-dimethyl-formamide;	4-Cyano-4-(2,4-difluorophenyl)-piperidine-1-carboxylic acid tert-butyl ester. To bis(2-chloroethyl)-carbamic acid tert-butyl ester (1.0 g, 3.8 mmol) and 2,4-difluorophenyl acetonitrile (0.581 g, 3.8 mmol) in DMF (35 ml), NaH (95%) (0.258 g, 9.68 mmol) was added in one batch at 0 C. The solution was stirred for 10 minutes at room temperature. When foaming subsided, the solution was heated at 60 C. for 24 hours. It was then quenched with water at 0 C. and concentrated. The residue was extracted with ethyl acetate (25 mL) and washed three times with water (15 mL). The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (hexane:ethyl acetate 4:1) yielded 0.720 g (62%) of the product as a syrup.

References: [1]Bioorganic and medicinal chemistry letters,2000,vol. 10,p. 1625 - 1628.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 2703 - 2718.
[3]Patent: US6245773,2001,B1 .

11
[ 656-35-9 ]
[ 134672-72-3 ]