2339-58-4|3-Fluoro-5-methoxyaniline| Ambeed

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Quality Control of [ 2339-58-4 ] Purity: 98% SDS Specification

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Product Details of [ 2339-58-4 ]

CAS No. :	2339-58-4
Formula :	C₇H₈FNO
M.W :	141.14
SMILES Code :	COC1=CC(N)=CC(F)=C1
MDL No. :	MFCD00077535
InChI Key :	BHWSRJOKTBUWBN-UHFFFAOYSA-N
Pubchem ID :	40427890

Safety of [ 2339-58-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 2339-58-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	37.3
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.61
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	1.31
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.84
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.	1.58
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	1.53
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.58

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.92
Solubility	1.7 mg/ml ; 0.0121 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.65
Solubility	3.15 mg/ml ; 0.0223 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	-2.42
Solubility	0.538 mg/ml ; 0.00381 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	No
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.	-6.23 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	1.0 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)	1.34

Application In Synthesis of [ 2339-58-4 ]

* 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 [ 2339-58-4 ]

[ 2339-58-4 ] Synthesis Path-Downstream 1~35

1
[ 7087-60-7 ]
[ 2339-58-4 ]

References: [1]Journal of the American Chemical Society,2011,vol. 133,p. 15686 - 15696.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 629 - 633.
[3]Anales des la Asociacion Quimica Argentina,1936,vol. 24,p. 119,124, 127.
An. Soc. cient. arg.,1938,vol. 125,p. 55.
[4]Journal of the Chemical Society. Perkin transactions II,1977,p. 14 - 17.

2
[ 2339-58-4 ]
[ 29578-39-0 ]

References: [1]Patent: US3671636,1972, .
Chem.Abstr.,1972,vol. 77.

3
[ 88-88-0 ]
[ 2339-58-4 ]
[ 62606-10-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions II,1977,p. 14 - 17.
[2]Journal of the Chemical Society. Perkin transactions II,1977,p. 14 - 17.

Yield	Reaction Conditions	Operation in experiment
79%	With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide; In dimethyl sulfoxide; at 110℃; for 24h;Inert atmosphere; Schlenk technique;	General procedure: Example 9 Synthesis of Aromatic Amines Copper iodide (0.05 mmol), ligand L-II-71 (0.05 or 0.1 mmol), potassium phosphate (1.1 mmol) were added into a 10 mL of Schlenk tube. The tube was then evacuated and backfilled with argon (this sequence was repeated three times), and then aryl chloride (1.0 mmol), 1 mL of DMSO and ammonium hydroxide (2.0 mmol) were added. The reaction mixture was well stirred at 110C. or 120C. for 24 hours. After cooling, water and ethyl acetate were added and mixture was separated. The aqueous phase was extracted twice with ethyl acetate. The combined organic phase was dried over anhydrous sodium sulfate. After concentration, the residue was purified by column chromatography to give the product aromatic amines.

6
[ 2339-58-4 ]
[ 36699-70-4 ]

References: [1]Patent: US3671636,1972, .
Chem.Abstr.,1972,vol. 77.

7
[ 2339-58-4 ]
[ 29578-41-4 ]

References: [1]Patent: US3671636,1972, .
Chem.Abstr.,1972,vol. 77.

8
[ 2339-58-4 ]
erythro-5-Fluor-3-methoxy-α-(1-aminoethyl)-benzylalkohol [ No CAS ]

References: [1]Patent: US3671636,1972, .
Chem.Abstr.,1972,vol. 77.

9
[ 7087-60-7 ]
[ 7440-66-6 ]
[ 2339-58-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	With ammonium chloride; In methanol; hexane; ethyl acetate;	Step 2. 3-Fluoro-5-methoxyphenylamine. Compound 170 was dissolved in methanol (25 ml) and was treated with zinc powder (1.96 g, 30 mmol) then saturated ammonium chloride solution (20 ml) in small portions. The mixture was stirred vigorously for 5 hours then filtered through a pad of Celite and concentrated under reduced pressure. The residue was partitioned between ethyl acetate (25 ml) and brine (20 ml). The organic material was separated, dried (MgSO4) then concentrated under reduced pressure. The residue was flushed through a pad of silica gel with 3:1 hexane/ethyl acetate to give 3-fluoro-5-methoxyaniline (171) as a yellow solid (0.404 g, 54%).

References: [1]Patent: US2005/54850,2005,A1 .

10
[ 6191-99-7 ]
[ 2339-58-4 ]
C₁₂H₁₄FNO₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 629 - 633.

11
[ 2339-58-4 ]
[ 26413-58-1 ]
ammonium thiocyanate [ No CAS ]
[ 1145355-37-8 ]

Yield	Reaction Conditions	Operation in experiment
73%		Description 13 l-(2-Chloro-6-methyl-pyridine-4-carbonyl)-3-(3-fluoro-5-methoxy-phenyl)- thiourea (D13)2-Chloro-6-methyl-4-pyridinecarbonyl chloride (44.087 g, 0.232 mol) in acetone (1 1) was treated with ammonium isothiocyanate (21.192 g, 0.278 mol) and the mixture was stirred for 1 hour at room temperature. Subsequently, a solution of 3-fluoro-5- methoxybenzenamine (36.02 g, 0.255 mol) in acetone (200 ml) was added dropwise and the reaction mixture was stirred for 4 hours at room temperature. The solvent was evaporated in vacuo and the residue was dissolved in CH2Cl2 (1 1). This organic solution was washed (H2O), dried (MgSO4), filtered and the solvent was evaporated in vacuo to yield a brown solid. The brown solid was triturated in acetonitrile (0.8 1), stirred overnight and the solid was filtered off and dried (vacuum oven, 4 hours at 65 0C). Yield: 59.69 g of intermediate D13 (73 %).

References: [1]Patent: WO2009/50186,2009,A1 .Location in patent: Page/Page column 28.

12
[ 202925-08-4 ]
[ 2339-58-4 ]

References: [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 4071 - 4074.
[2]Organic Letters,2013,vol. 15,p. 3734 - 3737.
[3]Organic Letters,2015,vol. 17,p. 5934 - 5937.
[4]Chemistry - A European Journal,2013,vol. 19,p. 2131 - 2141.

13
[ 2339-58-4 ]
[ 1296271-50-5 ]
[ 1296270-70-6 ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 943 - 962.

14
[ 2339-58-4 ]
C₁₆H₈FN₃O₃ [ No CAS ]