1025718-84-6|3-Bromo-5-(trifluoromethyl)phenol| Ambeed

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Quality Control of [ 1025718-84-6 ] Purity: 95% SDS Specification

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Product Details of [ 1025718-84-6 ]

CAS No. :	1025718-84-6
Formula :	C₇H₄BrF₃O
M.W :	241.01
SMILES Code :	OC1=CC(C(F)(F)F)=CC(Br)=C1
MDL No. :	MFCD11041083
InChI Key :	BWJBVICFLRSNNM-UHFFFAOYSA-N
Pubchem ID :	21079740

Safety of [ 1025718-84-6 ]

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

Computational Chemistry of [ 1025718-84-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	41.17
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.23 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.83
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	3.14
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.33
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.	3.3
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	3.05
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.62
Solubility	0.0583 mg/ml ; 0.000242 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.	-3.23
Solubility	0.14 mg/ml ; 0.000583 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	-3.57
Solubility	0.0653 mg/ml ; 0.000271 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.	-5.54 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)	1.55

Application In Synthesis of [ 1025718-84-6 ]

* 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 [ 1025718-84-6 ]

[ 1025718-84-6 ] Synthesis Path-Downstream 1~35

1
[ 557-21-1 ]
[ 1025718-84-6 ]
[ 1243459-56-4 ]

Yield	Reaction Conditions	Operation in experiment
96.7%	tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 90℃; for 2.0h;	Synthesis of Intermediate (1)(1 )Molecular Weig ht: 241.01 Molecular Weig ht: 187.12[00627] In a 3-neck 100 mL round-bottomed flask, stirred solution of 3-bromo-5- (trif uoromethyl)phenol (2 g, 1 eq.) in DMF(25 mL, 25 Vol) was degassed. ZN(CN)2 (0.68 g, 0.7 eq.) and Pd[P(Ph)3]4 (1.9 g, 0.2 eq.) was added in reaction and heat at 90C for 2 h. Reaction completion was monitored on TLC using ethyl acetate: hexane (2:8) mobile phase. Reaction mixture was brought to room temperature and quenched into the ice-water slurry (200 mL) and compound was extracted in the ethyl acetate (50 mL x 3). Organic layer was washed with brine solution (50 mL x 3) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 1.5 g of crude compound which was purified by column chromatography using ethyl acetate and Hexane as mobile phase. Product was eluted in 6% ethyl acetate in Hexane to afford 1.5 g of pure compound. Yield (96.7 %). Mass: 187.9.
60%	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃; for 4.0h;Inert atmosphere;	To a solution of <strong>[1025718-84-6]3-bromo-5-trifluoromethylphenol</strong> (7.2 g, 30 mmol) in DMF (100 mL) was added Zn(CN)2 (3.51 g, 30 mmol) and Pd(PPh3)4 (3.5 g, 6 mmol). The resulting mixture was stirred at 100 C under nitrogen atmosphere for 4 hours. EtOAc (250 mL) was added and the mixture was washed with water (2 x 50 mL) and brine (100 mL) before it was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20% EtOA in hexane) to give a cololess oil (3.36 g, 60%).

References: [1]Patent: WO2011/109799,2011,A1 .Location in patent: Page/Page column 239-240; 272.
[2]Patent: WO2016/187393,2016,A1 .Location in patent: Paragraph 0212.

2
[ 1025718-84-6 ]
[ 1333153-81-3 ]

References: [1]Patent: WO2011/109799,2011,A1 .

3
[ 1025718-84-6 ]
[ 1333153-82-4 ]

References: [1]Patent: WO2011/109799,2011,A1 .

4
[ 1025718-84-6 ]
C₁₁H₁₂F₃NO₂S [ No CAS ]

References: [1]Patent: WO2011/109799,2011,A1 .

5
[ 1025718-84-6 ]
[ 1333153-84-6 ]

References: [1]Patent: WO2011/109799,2011,A1 .

6
[ 1025718-84-6 ]
[ 1333154-09-8 ]

References: [1]Patent: WO2011/109799,2011,A1 .

7
[ 1025718-84-6 ]
[ 1333152-21-8 ]

References: [1]Patent: WO2011/109799,2011,A1 .

8
[ 1025718-84-6 ]
[ 73183-34-3 ]
[ 1256944-93-0 ]

Yield	Reaction Conditions	Operation in experiment
40%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 2.0h;Inert atmosphere;	[00530] Synthesis of 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-5- (trifluoromethyl)phenol (182): 3-Bromo-5-(trifluoromethyl)phenol (181; 2.5 g, 10 mmol), 4j4;4'j4';5;5,5';5'.0ctamethyl-2,2'-bi(l,3,2-dioxaborolane) (3.8 g, 15 mmol), Pd(dppf)Cl2 (1.1 g, 1.5 mmol), and potassium acetate (2 g, 20 mmol) were added in 50 mL of dioxane and degassed. The reaction mixture was heated at 80 C under nitrogen atmosphere for 2 h. After cooling down to room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure to give the crude product, which was purified by silica gel chromatography (10% EtO Ac/petroleum ether) to yield 1.2 g of 3-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenol (182) as white solid (40% yield). LCMS: m/z 289.1 , = 1.77 min.

References: [1]Patent: WO2015/42414,2015,A1 .Location in patent: Paragraph 00530.

9
[ 1025718-84-6 ]
[ 1432912-67-8 ]
4-[3-bromo-5-(trifluoromethyl)phenoxy]-2,5-difluoro-N-methyl-N-(1,2,4-thiadiazol-5-yl)benzene-1-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2.0h;	Into a 25-m L round-bottom flask was placed a solution of 2,4,5-trifluoro-N-methyl-N-(1 ,2,4- thiadiazol-5-yl)benzene-1 -sulfonamide (140 mg, 0.45 mmol, 1 .00 equiv) in N,N-dimethylformamide (10 m L). To the solution were added potassium carbonate (125 mg, 0.90 mmol, 2.00 equiv) and 3-bromo-5- (trifluoromethyl)phenol (1 09 mg, 0.45 mmol, 1 .00 equiv). The solution was stirred for 2 hours at room temperature and the reaction was then quenched by the addition of 10 m L of water. The resulting solution was extracted with 50 mL of ethyl acetate and the combined organic layers were washed with brine (4x20 m L), dried over anhydrous sodium sulfate and concentrated under vacuum . The crude product (100 mg) was purified by flash-prep-HPLC with the following conditions (lntelFlash-1 ) : column, C18 silica gel; mobile phase, acetonitrile/water with N H4HC03 = 35:65 increasing to acetonitrile/water with NH4HC03 = 85:15 within 8 min; detector, UV 254 nm . This resulted in 37.6 mg (16%) of 4-[3-bromo-5- (trifluoromethyl)phenoxy]-2,5-difluoro-N-methyl-N-(1 ,2,4-thiadiazol-5-yl)benzene-1 -sulfonamide, the final product, as a white solid. (0249) LC-MS (ES, m/z) : [M+H]+ = 531 . (0250) H-NMR: (400 MHz, DMSO-d6, ppm) : delta 8.44 (m, 1 H), 8.12-8.06 (m , 1 H), 7.85 (s, 2H), 7.69 (m, 1 H), 7.52- 7.46 (m, 1 H), 3.49-3.46 (s, 3H).

References: [1]Patent: WO2015/130957,2015,A1 .Location in patent: Page/Page column 50.

10
[ 1025718-84-6 ]
[ 165047-24-5 ]
4-[3-bromo-5-(trifluoromethyl)phenoxy]-2,5-difluorobenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1.0h;	Into a 25-m L round-bottom flask was placed a solution of 2,4,5-trifluorobenzaldehyde (500 mg, 3.12 mmol, 1 .00 equiv) in N,N-dimethylformamide (10 mL). To the solution were added potassium carbonate (862 mg, 6.24 mmol, 2.00 equiv) and <strong>[1025718-84-6]3-bromo-5-(trifluoromethyl)phenol</strong> (753 mg, 3.12 mmol, 1 .00 equiv). The solution was stirred for 1 hour at room temperature and then quenched by the addition of 10 mL of water. The resulting solution was extracted with 50 m L of ethyl acetate and the combined organic layers were washed with brine (4 x 20 m L), dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 1 .1 g (92%) of 4-[3-bromo-5-(trifluoromethyl)phenoxy]-2,5- difluorobenzaldehyde as a yellow solid

References: [1]Patent: WO2015/130957,2015,A1 .Location in patent: Page/Page column 46.

11
[ 1025718-84-6 ]
[ 1235406-89-9 ]
4-[3-bromo-5-(trifluoromethyl)phenoxy]-N-[(2,4-dimethoxyphenyl)methyl]-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzene-1-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16.0h;	Into a 50-m L round-bottom flask, was placed a solution of N-[(2,4-dimethoxyphenyl)methyl]-2,4,5- trifluoro-N-(1 ,2,4-thiadiazol-5-yl)benzene-1 -sulfonamide (150 mg, 0.34 mmol, 1 .00 equiv) in N,N- dimethylformamide (20 mL). To the solution were added <strong>[1025718-84-6]3-bromo-5-(trifluoromethyl)phenol</strong> (81 mg, 0.34 mmol, 1 .00 equiv) and Cs2C03 (220 mg, 0.67 mmol, 2.00 equiv). The resulting solution was stirred for 16 h at room temperature. The resulting solution was extracted with ethyl acetate (3x20 m L) and the organic layers combined and concentrated under vacuum . The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :5). This resulted in 170 mg (76%) of 4-[3-bromo-5- (0624) (trifluoromethyl)phenoxy]-N-[(2,4-dimethoxyphenyl)methyl]-2,5-difluoro-N-(1 ,2,4-thiadiazol-5-yl)benzene- 1 -sulfonamide as a white solid.

References: [1]Patent: WO2015/130957,2015,A1 .Location in patent: Page/Page column 96.

12
[ 1025718-84-6 ]
[ 1235406-89-9 ]
4-[3-bromo-5-(trifluoromethyl)phenoxy]-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzene-1-sulfonamide [ No CAS ]

References: [1]Patent: WO2015/130957,2015,A1 .

13
[ 1025718-84-6 ]
[ 824-94-2 ]
1-bromo-3-((4-methoxybenzyl)oxy)-5-(trifluoromethyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		To a stirred solution of <strong>[1025718-84-6]3-bromo-5-(trifluoromethyl)phenol</strong> (3.0 g, 12.45 mmol) in DMF (30 mL) was added, potassium carbonate (6.9 g, 49.8 mmol) and the mixture was stirred for 10 mins. Then, l-(chloromethyl)-4-methoxybenzene (2.5 mL, 18.7 mmol) was added and the reaction mixture was heated to 60 C overnight. After completion, the mixture was diluted with ice water (100 mL), extracted with Ethyl acetate (250 mL X 2), washed with water, brine and the combined organic layers were dried and filtered. The solvent was removed under reduced pressure and the crude product was purified by flash chromatography to furnish the titled compound (4.1 g, 91%) as colorless oil.

References: [1]Patent: WO2015/162538,2015,A1 .Location in patent: Page/Page column 33; 63.

14
[ 1025718-84-6 ]
(R)-ethyl 5-(3-(2-((1-(3-methoxyphenyl)ethyl)amino)ethoxy)-5-(trifluoromethyl)phenyl)-3-methylbenzofuran-2-carboxylate [ No CAS ]