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Quality Control of [ 53764-99-1 ] Purity: 97% SDS Specification

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Product Details of [ 53764-99-1 ]

CAS No. :	53764-99-1
Formula :	C₁₁H₉F₃O₂
M.W :	230.18
SMILES Code :	O=C(C1=CC=CC(C)=C1)CC(C(F)(F)F)=O
MDL No. :	MFCD11849497
InChI Key :	VOFWLZQTWRLBTR-UHFFFAOYSA-N
Pubchem ID :	18624099

Safety of [ 53764-99-1 ]

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

Computational Chemistry of [ 53764-99-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	6
Fraction Csp3	0.27
Num. rotatable bonds	4
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	51.61
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	34.14 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.94
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	3.12
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.96
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.	2.1
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	3.48
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.92

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.25
Solubility	0.131 mg/ml ; 0.000567 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.	-3.51
Solubility	0.0718 mg/ml ; 0.000312 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	-3.98
Solubility	0.0241 mg/ml ; 0.000105 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	Yes
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.	-5.49 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.	0.55

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)	1.43

Application In Synthesis of [ 53764-99-1 ]

* 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.

Upstream synthesis route of [ 53764-99-1 ]
Downstream synthetic route of [ 53764-99-1 ]

[ 53764-99-1 ] Synthesis Path-Upstream 1~2

1
[ 400-38-4 ]
[ 585-74-0 ]
[ 53764-99-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium methylate In toluene for 4 h; Reflux	To a solution of isopropyl 2,2,2-trifluoroacetate 10 (7.40g, 0.0474mol) in toluene (15 mL) was added and 3’-methylacetophenone 11 (6.36g, 0.0474mol) and cooled to 0°C, followed by dropwise addition Sodium methoxide (3.0g, 0.0616 mol) to the reaction mixture. The reaction mixture was heated to reflux. After stirring for 4 h, the reaction mixture was diluted with water (275 mL), brine (275 mL), EtOAc (500 mL). The aqueous layer was separated and extracted with EtOAc (200 mL x 4). The combined organic phases were washed with brine (500 mL x 1), dried over Na₂SO₄ and concentrated under vacuum. The crude product purified by flash column chromatography to give 4,4,4-trifluoro-1-(m-tolyl)butane-1,3-dione, 8 as a white solid (9.5g, 87percent yield). To a 500 mL round-bottomed flask containing ethyl acetate (20 mL) and water (16 mL) was added 4,4,4-trifluoro-1-(m-tolyl)butane-1,3-dione 8 (4.0g, 0.0174mol), the reaction mixture was cooled to 0°C and stirred for 15 min. 4-hydrazinobenzenesulfonamide hydrochloride7 (4.0g, 0.0214 mol) was added to the reaction mixture slowly. The reaction was refluxed for 8 h then cooled to rt. The solid precipitated on cooling was filtered, the filtered solid was washed with cold isopropyl alcohol (20mL X 2) to give the the impurity A 2 as white solid (5.15g) with an excellent yield of 92.0percent. 4-(5-(m-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide (2) ¹H NMR (400 MHz, DMSO - d₆) δ 7.94 – 7.79 (m, 2H), 7.60 – 7.45 (m, 4H), 7.21 (dd, J = 10.9, 5.1 Hz, 4H), 7.08 – 6.89 (m, 1H), 2.25 (s, 3H). ¹³C NMR(101 MHz, DMSO - d₆) δ 145.82, 144.54, 142.86, 142.45, 141.59, 138.80, 130.57, 130.04, 129.18, 128.69, 127.31, 126.51, 121.86 (q, J = 265 Hz), 106.91, 21.42. ¹⁹F NMR (376 MHz, DMSO - d₆) δ -60.77. HRMS m/z (M-H)^-: 380.0695; calculated for C₁₇H₁₄F₃N₃O₂S; 380.0686

References: [1] Bulletin of the Korean Chemical Society, 2019, .

2
[ 383-63-1 ]
[ 585-74-0 ]
[ 53764-99-1 ]

References: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 5, p. 1531 - 1535.
[2] Journal of Medicinal Chemistry, 1997, vol. 40, # 9, p. 1347 - 1365.
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 2, p. 499 - 504.
[4] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 12, p. 3406 - 3413.

[ 53764-99-1 ] Synthesis Path-Downstream 1~28

1
[ 53764-99-1 ]
[ 17852-52-7 ]
4-[5-(3-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In water; ethyl acetate; for 8h;Reflux;	To a solution of isopropyl 2,2,2-trifluoroacetate 10 (7.40g, 0.0474mol) in toluene (15 mL) was added and 3?-methylacetophenone 11 (6.36g, 0.0474mol) and cooled to 0C, followed by dropwise addition Sodium methoxide (3.0g, 0.0616 mol) to the reaction mixture. The reaction mixture was heated to reflux. After stirring for 4 h, the reaction mixture was diluted with water (275 mL), brine (275 mL), EtOAc (500 mL). The aqueous layer was separated and extracted with EtOAc (200 mL x 4). The combined organic phases were washed with brine (500 mL x 1), dried over Na2SO4 and concentrated under vacuum. The crude product purified by flash column chromatography to give <strong>[53764-99-1]4,4,4-trifluoro-1-(m-tolyl)butane-1,3-dione</strong>, 8 as a white solid (9.5g, 87% yield). To a 500 mL round-bottomed flask containing ethyl acetate (20 mL) and water (16 mL) was added <strong>[53764-99-1]4,4,4-trifluoro-1-(m-tolyl)butane-1,3-dione</strong> 8 (4.0g, 0.0174mol), the reaction mixture was cooled to 0C and stirred for 15 min. 4-hydrazinobenzenesulfonamide hydrochloride7 (4.0g, 0.0214 mol) was added to the reaction mixture slowly. The reaction was refluxed for 8 h then cooled to rt. The solid precipitated on cooling was filtered, the filtered solid was washed with cold isopropyl alcohol (20mL X 2) to give the the impurity A 2 as white solid (5.15g) with an excellent yield of 92.0%. 4-(5-(m-tolyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide (2) 1H NMR (400 MHz, DMSO - d6) delta 7.94 - 7.79 (m, 2H), 7.60 - 7.45 (m, 4H), 7.21 (dd, J = 10.9, 5.1 Hz, 4H), 7.08 - 6.89 (m, 1H), 2.25 (s, 3H). 13C NMR(101 MHz, DMSO - d6) delta 145.82, 144.54, 142.86, 142.45, 141.59, 138.80, 130.57, 130.04, 129.18, 128.69, 127.31, 126.51, 121.86 (q, J = 265 Hz), 106.91, 21.42. 19F NMR (376 MHz, DMSO - d6) delta -60.77. HRMS m/z (M-H)-: 380.0695; calculated for C17H14F3N3O2S; 380.0686

References: [1]Bulletin of the Korean Chemical Society,2019,vol. 40,p. 479 - 480.
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365.

2
[ 383-63-1 ]
[ 585-74-0 ]
[ 53764-99-1 ]

References: [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 1531 - 1535.
[2]Journal of Medicinal Chemistry,1997,vol. 40,p. 1347 - 1365.
[3]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 499 - 504.
[4]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3406 - 3413.

3
[ 53764-99-1 ]
4-hydrazino-2-hydroxymethyl-1-benzenesulfonamide hydrochloride [ No CAS ]
2-hydroxymethyl-4-(5-m-tolyl-3-trifluoromethyl-pyrazol-1-yl)-benzenesulfonamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 499 - 504.

4
[ 53764-99-1 ]
[ 60-34-4 ]
[ 905844-17-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5370 - 5383.

5
[ 53764-99-1 ]
[ 905844-18-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5370 - 5383.

6
[ 53764-99-1 ]
N-(4-chloro-phenyl)-3-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-benzamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 5370 - 5383.

Yield	Reaction Conditions	Operation in experiment
		4,4,4-Trifluoro-1-m-tolyl-butane-1,3-dione 1H-NMR (CDCl3): delta15.16 (bs, 1H), 7.76 (s, 1H), 7.74 (d, J=7.2 Hz, 1H), 7.45-7.38 (m, 2H), 6.56 (s, 1H), 2.44 (s, 3H). The following compounds were prepared in a manner similar to that described above. 1H-NMR (CDCl3): delta15.0 (br, 1H), 7.60 (m, 1 H), 7.47 (m, 1 H), 7.33 (m, 2 H), 6.36 (s, 1 H), 2.57 (s, 3 H). 1H-NMR (CDCl3): delta15.1 (br, 1 H), 7.83 (d, J=8.2 Hz, 2 H), 7.29 (d, J=8.2 Hz, 2 H), 6.52 (s, 1 H), 2.43 (s, 3 H). 1H-NMR (CDCl3): delta14.8 (br, 1 H), 7.71 (d, J=8.6 Hz, 2 H), 7.33 (d, J=8.6 Hz, 2 H), 6.30 (s, 1 H). 1H-NMR (CDCl3): delta14.7 (br, 1 H), 7.90 (m, 1 H), 7.80 (d, J=8.0 Hz, 1 H), 7.57 (d, J=8.0 Hz, 1 H), 7.44 (m, 1 H), 6.52 (s, 1 H). 1H-NMR (CDCl3): delta14.4 (br, 1 H), 7.68 (m, 1H), 7.48 (m, 1 H), 7.47 (m, 1 H), 7.39 (m, 1 H), 6.56 (s, 1 H). 1H-NMR (CDCl3): delta15.09 (br, 1 H), 7.51 (m, 1 H), 7.46 (m, 1 H), 7.41 (m, 1 H), 7.16 (m, 1 H), 6.56 (s, 1 H), 3.88 (s, 3 H). 1H-NMR (CDCl3): delta15.18 (br, 1 H), 7.77 (m, 1 H), 7.75 (m, 1 H), 7.46 (m, 1 H), 7.43 (m, 1 H), 6.57 (s, 1 H), 2.73 (q, J=7.7 Hz, 2 H), 1.28 (t, J=7.7 Hz, 3 H). 1H-NMR (CDCl3): delta14.89 (br, 1 H), 8.19 (s, 1 H), 8.13 (d, J=8.1, 1 H), 7.88 (d, J=8.3 Hz, 1 H), 7.67 (m, 1 H), 6.60 (s, 1 H). 1H-NMR (CDCl3): delta14.75 (br, 1H), 8.78 (m, 1H), 8.48 (m, 1H), 8.29 (m, 1 H), 7.76 (t, J=8 Hz, 1 H), 6.66 (s, 1H). 1H-NMR (CDCl3): delta15.25 (br, 1H), 8.0 (m, 1 H), 7.56 (m, 1 H), 7.10 (m, 1 H), 7.02 (m, 1 H), 3.98 (s, 3 H). 1H-NMR (CDCl3): delta15.4 (br, 1H), 7.92 (d, J=8.8 Hz, 2 H), 6.97 (d, J=8.8 Hz, 2 H), 6.48 (s, 1 H), 3.89 (s, 3 H).

8
[ 53764-99-1 ]
2-fluoro-1-(m-tolyl)-2-(2-(p-tolyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)ethanone [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1277 - 1282.

9
[ 53764-99-1 ]
2,4,4,4-tetrafluoro-3,3-dihydroxy-1-m-tolylbutan-1-one [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1277 - 1282.

10
[ 53764-99-1 ]
[ 50562-05-5 ]

References: [1]Organic and Biomolecular Chemistry,2016,vol. 14,p. 1531 - 1535.

11
[ 6018-41-3 ]
[ 53764-99-1 ]
methyl 3-(3-methylbenzoyl)-4-(trifluoromethyl)benzoate [ No CAS ]

References: [1]Green Chemistry,2018,vol. 20,p. 1491 - 1498.

12
[ 53764-99-1 ]
[ 34547-26-7 ]
1-(5-hydroxy-3-(m-tolyl)-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-(2-methoxyphenyl)ethan-1-one [ No CAS ]