195447-79-1|3-Fluoro-5-(trifluoromethyl)phenylacetic Acid| Ambeed

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Quality Control of [ 195447-79-1 ] Purity: 98% SDS Specification

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Product Details of [ 195447-79-1 ]

CAS No. :	195447-79-1
Formula :	C₉H₆F₄O₂
M.W :	222.14
SMILES Code :	O=C(O)CC1=CC(C(F)(F)F)=CC(F)=C1
MDL No. :	MFCD00061188
InChI Key :	LQIBHDUPSIQRPV-UHFFFAOYSA-N
Pubchem ID :	2759172

Safety of [ 195447-79-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405-P501

Computational Chemistry of [ 195447-79-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	3
Num. H-bond acceptors	6.0
Num. H-bond donors	1.0
Molar Refractivity	42.95
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.67
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.	4.04
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.	3.11
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	3.04
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.85

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.81
Solubility	0.345 mg/ml ; 0.00155 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.	-2.79
Solubility	0.357 mg/ml ; 0.00161 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	-3.35
Solubility	0.0995 mg/ml ; 0.000448 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	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

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)	1.93

Application In Synthesis of [ 195447-79-1 ]

* 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 [ 195447-79-1 ]

[ 195447-79-1 ] Synthesis Path-Downstream 1~14

1
[ 67-56-1 ]
[ 195447-79-1 ]
[ 955036-78-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; In water; for 2.5h;Heating / reflux;	Example 12 Synthesis of Ester Precursors to Compounds of Formula II Methyl 3-fluoro-5-trifluorophenylacetate A mixture of <strong>[195447-79-1]3-Fluoro-5-trifluoromethyl-phenylacetic acid</strong> (4.72 g, 21.2 mmol) and concentrated HCl (1.2 mL) in MeOH (50 mL) was refluxed for 2.5 h, then concentrated in vacuo. The residue was partitioned between 100 mL of EtOAc and washed sequentially with 0.5N aqueous NaOH (30 mL), 2% NaHCO3 solution (30 mL), and brine (30 mL). The EtOAc layer was dried (Na2SO4), filtered, and concentrated to provide 5.01 g (quantitative) of methyl 3-fluoro-5-trifluoromethyl-phenylaceiate as a colorless oil: 1H NMR (CDCl3, 300 MHz) delta 3.69 (s, 2H), 3.73 (s, 3H), 7.21-7.73 (m, 3H).

References: [1]Patent: US2007/293548,2007,A1 .Location in patent: Page/Page column 67.

2
[ 195447-79-1 ]
[ 955038-21-8 ]

Yield	Reaction Conditions	Operation in experiment
94%		Example 13 Synthesis of Aldehyde Precursors to Compounds of Formula II 3-Fluoro-5-trifluoromethyl-phenylacetaldehyde To a solution of 5.0 g (21.2 mmol) of methyl-3-fluoro-5-trifluorophenylacetate in 21.2 mL of CH2Cl2 and 10.6 mL of hexane, cooled to -70 C. in an argon atmosphere, was added 17.0 mL (25.4 mmol) of a 1.5M solution of DIBAL-H in toluene over approximately two minutes. The mixture was allowed to warm to -50 C. over 1 h, and 21.2 mL of MeOH was added, followed by 14 mL of 6 N HCl and 21.2 mL of H2O. The mixture was extracted with EtOAc, and the EtOAc layer was washed sequentially with H2O and brine, dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography (¼ EtOAc/hexane) to provide 4.10 g (94%) of product as a colorless oil: 1H NMR (CDCl3) delta 3.82 (s, 2H), 7.11-7.31 (m, 3H), 9.80 (s, 1H).

References: [1]Patent: US2007/293548,2007,A1 .Location in patent: Page/Page column 68.

3
[ 195447-79-1 ]
[ 100-51-6 ]
[ 1182351-34-3 ]

Yield	Reaction Conditions	Operation in experiment
		Example 25; Synthesis of {3-[4-(2,2-Dimethyl-propionylamino)-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-5-trifluoromethyl-phenyl}-acetic acid (Compound 32)To benzyl alcohol (1.1 g, 10 mmol) in NMP (20 mL) was added sodium hydride (60% in mineral oil; 0.44 g, 11 mmol), and the mixture was stirred for 30 minutes at room temperature. The mixture was then added to a vial containing <strong>[195447-79-1]3-fluoro-5-(trifluoromethyl)phenylacetic acid</strong> (1 g, 4.5 mmol), and the reaction was stirred at 120 C. for 3 hours. Acidic work-up gave (3-benzyloxy-5-trifluoromethyl-phenyl)-acetic acid the title compound.

References: [1]Patent: US2010/4331,2010,A1 .Location in patent: Page/Page column 16.

4
[ 195447-79-1 ]
5-(2,3-dihydro-1H-indol-5-yl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine dihydrochloride [ No CAS ]
[ 1337531-89-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7193 - 7207.

5
[ 195447-79-1 ]
2-(3-fluoro-5-(trifluoromethyl)phenyl)-1-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-1-yl)ethanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1426 - 1441.

6
[ 195447-79-1 ]
1-(5-(4-amino-2,7-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)indolin-1-yl)-2-(3-fluoro-5-(trifluoromethyl)phenyl)ethanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 1426 - 1441.

7
[ 22190-33-6 ]
[ 195447-79-1 ]
1-(5-bromoindolin-1-yl)-2-(3-fluoro-5-(trifluoromethyl)phenyl)ethanone [ No CAS ]