94088-46-7|2-Fluoro-6-methoxybenzonitrile| Ambeed

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Quality Control of [ 94088-46-7 ] Purity: 95% SDS Specification

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Product Details of [ 94088-46-7 ]

CAS No. :	94088-46-7
Formula :	C₈H₆FNO
M.W :	151.14
SMILES Code :	N#CC1=C(OC)C=CC=C1F
MDL No. :	MFCD00042291
InChI Key :	YPMSIWYNTPSPMV-UHFFFAOYSA-N
Pubchem ID :	523101

Safety of [ 94088-46-7 ]

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

Computational Chemistry of [ 94088-46-7 ] 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	37.61
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.02 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.84
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	1.71
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.13
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.	1.55
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	2.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.89

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.19
Solubility	0.971 mg/ml ; 0.00643 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.	-2.02
Solubility	1.45 mg/ml ; 0.00957 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	-2.87
Solubility	0.203 mg/ml ; 0.00134 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.	-6.01 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)	1.54

Application In Synthesis of [ 94088-46-7 ]

* 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.

Downstream synthetic route of [ 94088-46-7 ]

[ 94088-46-7 ] Synthesis Path-Downstream 1~42

1
[ 150-19-6 ]
[ 94088-46-7 ]
2-Methoxy-6-(3-methoxy-phenoxy)-benzonitrile [ No CAS ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 3229 - 3230.
[2]Journal of Organic Chemistry,1998,vol. 63,p. 6338 - 6343.

2
[ 1897-52-5 ]
[ 124-41-4 ]
[ 94088-46-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	In methanol; at 0 - 20℃;	Synthesis Route 21.5: 2-Fluoro-6-methoxybenzonitrile (analogous to WO 99/14187):640.5 g (4.6 mol) of difluorobenzonitrile were dissolved in 3.5 I of methanol and then cooled to 0-50C. 828.8 g of 30% strength sodium methoxide solution were added dropwise in this temperature range, and the reaction mixture was stirred at room temperature overnight. Then the reaction mixture was added to 20 I of water and the precipitate was filtered off with suction and washed twice with water and twice with heptane. The solid was dried in vacuo at 50C. Yield: 740 g (99% of theory) of a white solid with a purity of >95% according to GC.1H NMR (in CDCI3): delta = 3.95 ppm (s, 3H, 0-CH3), 6.85 ppm (m, 2H, arom. H), 7.5 ppm (q, 1H, arom. H). ;
	In methanol; at 0 - 20℃;	I. Synthesis Examples; Example 1.1 : 2-Difluoromethoxy-6-prop-2-ynylsulfamoyl-thiobenzamide (4); 1.1. 2-Fluoro-6-methoxybenzonitrile:; 640.5 g (4.6 mol) of difluorobenzonitrile have been dissolved in 3.5 I of methanol and then cooled to 0-5 C. 828.8 g of 30% strength sodium methoxide solution have been added dropwise in this temperature range, and the reaction mixture has been stirred at room temperature overnight. Then the reaction mixture has been added to 20 I of water and the precipitate has been filtered off with suction and washed twice with water and twice with heptane. The solid has been dried in vacuo at 50 C to yield 740 g (455 mmol) of the title compound as a white solid.
	In methanol; at 20℃;	To a solution of A6.1 (500 g, 3.6 mol) in 2.5 L MeOH was added sodium methoxide (388 g, 7.2 mol) in portions slowly. The mixture was stirred at rt overnight. The reaction mixture was poured into 15 L H2O and the precipitate was filtered off and washed twice with 2.0 L H2O to give the title compound (1140 g) as a white solid, the crude product will be used in next step without further purification. 1H NMR (500 MHz, CDCl3) delta ppm 3.96 (s, 3H), 6.79 (dd, 2H), 7.52 (dd, 1H)

In methanol; at 20℃;Large scale;

To a solution of A3.l (500 g, 3.6 mol) in 2.5 L MeOH was added sodium methoxide (388 g, 7.2 mol) in portions slowly. The mixture was stirred at rt overnight. The reaction mixture was poured into 15 L H20 andthe precipitate was filtered off and washed twice with 2.0 L H20 to give the title compound (1140 g) as a white solid, the crude product will be used in next step without further purification. 1H NMR (500 MHz, CDCI3) O ppm 3.96 (5, 3H), 6.79 (dd, 2H), 7.52 (dd, 1H).

References: [1]Patent: WO2006/56433,2006,A2 .Location in patent: Page/Page column 29.
[2]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1173 - 1177.
[3]Patent: WO2007/93530,2007,A1 .Location in patent: Page/Page column 244.
[4]Journal of Medicinal Chemistry,2012,vol. 55,p. 3135 - 3143.
[5]Patent: WO2017/221092,2017,A1 .Location in patent: Paragraph 00153.
[6]Patent: WO2017/221100,2017,A1 .Location in patent: Paragraph 000148.

3
[ 124-46-9 ]
[ 94088-46-7 ]
[ 27018-21-9 ]

Yield	Reaction Conditions	Operation in experiment
9.85 g	In N,N-dimethyl acetamide; at 140℃; for 8h;	General procedure: Example 1 Preparation of Compound Yhhu-0967 (5-methoxy-2,4-diaminoquinazoline) [0029] 2.53 g (79.08 mmol) of methanol was dropped into 5.18 g (86.27 mmol) of 40% sodium hydride suspension in tetrahydrofuran (150 ml) at 0 C. and stirred for 10 min, followed by dropwise addition of 10.0 g (71.89 mmol) of 2,6-difluorobenzonitrile in tetrahydrofuran (100 ml). The reaction mixture as stirred at room temperature for 10 h to complete the reaction. 200 ml of water was added thereto to destroy the excess sodium hydride, and the reaction mixture was extracted with 500 ml of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and evaporated to dryness. The residue was passed through column chromatography to provide an intermediate. The intermediate and 17.41 g (143.78 mmol) of guanidine carbonate were heated to 140 C. in 300 ml of N,N-dimethylacetamide and stirred for 8 h to complete the reaction. The reaction mixture was evaporated to dryness, then diluted with 200 ml of water and extracted with 400 ml of dichloromethane. The organic layer was dried with anhydrous sodium sulfate and then evaporated to dryness. The residue was passed through column chromatography to proved 9.85 g of compound Yhhu-0967 with a total yield of 72% in the two steps). [0030] 1H NMR (300 MHz, CHLOROFORM-d) d ppm 3.97 (s, 3H) 4.83 (br. s., 2H) 5.68 (br. s., 1H) 6.53 (d, J=8.06 Hz, 1H) 7.03 (d, J=8.55 Hz, 1H) 7.45 (t, J=8.18 Hz, 2H)

References: [1]Journal of Heterocyclic Chemistry,1988,vol. 25,p. 1173 - 1177.
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 3135 - 3143.
[3]Patent: US2013/261139,2013,A1 .Location in patent: Paragraph 0029-0030.

4
[ 594-19-4 ]
[ 94088-46-7 ]
6-Fluoro-2-methoxypivalophenone [ No CAS ]

References: [1]Magnetic Resonance in Chemistry,1994,vol. 32,p. 399 - 408.

5
[ 94088-46-7 ]
[ 137654-21-8 ]

References: [1]Journal of Organic Chemistry,1990,vol. 55,p. 4520 - 4522.
[2]Organic Letters,1999,vol. 1,p. 1491 - 1494.
[3]Journal of Organic Chemistry,2000,vol. 65,p. 3738 - 3753.

6
[ 94088-46-7 ]
[ 93-08-3 ]
[ 143306-35-8 ]
[ 143306-29-0 ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 5577 - 5585.

7
[ 546-88-3 ]
[ 94088-46-7 ]
[ 177995-40-3 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 2885 - 2886.

8
[ 94088-46-7 ]
[ 2365-48-2 ]
[ 35212-88-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With NaH; In dimethyl sulfoxide;	Methyl 3-amino-4-methoxybenzothiophene-2-carboxylate. Methyl thioglycollate (0.18 mL, 1.9 mmol) is added dropwise to a suspension of NaH (60% oil suspension, 176 mg, 4.4 mmol) in DMSO (5 mL), stirred under N2 at 25 C. When gas evolution ceases, <strong>[94088-46-7]2-fluoro-6-methoxybenzonitrile</strong> (266 mg, 1.76 mmol) in DMSO 5 mL is added in one portion. After 3 h, the reaction mixture is poured onto ice-water, and the beige precipitate is collected by suction filtration, rinsed and air dried to give methyl 3-amino-4-methoxybenzothiophene-2-carboxylate (345 mg, 83%). 1 H NMR (DMSO) delta7.44-7.37 (2H, m), 7.00, (2H brs), 6.90 (1H, d, J=7.7Hz), 3.95 (3H, s), 3.76 (3H, s).

References: [1]Patent: US5679683,1997,A .
[2]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1163 - 1172.

9
[ 171179-83-2 ]
[ 94088-46-7 ]

References: [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 1163 - 1172.

10
[ 621-23-8 ]
[ 75-29-6 ]
[ 94088-46-7 ]
2'-fluoro-2,4,6,6'-tetramethoxybenzophenone-N-(2-methylethyl)ketimine [ No CAS ]