[ CAS No. 1025718-84-6 ] {[proInfo.proName]}

Name: 1025718-84-6|3-Bromo-5-(trifluoromethyl)phenol|95%
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SKU: A236533
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Quality Control of [ 1025718-84-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1025718-84-6 ]

SDS Specification

Alternatived Products of [ 1025718-84-6 ]

Product Details of [ 1025718-84-6 ]

CAS No. :	1025718-84-6	MDL No. :	MFCD11041083
Formula :	C₇H₄BrF₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BWJBVICFLRSNNM-UHFFFAOYSA-N
M.W :	241.01	Pubchem ID :	21079740
Synonyms :

Calculated chemistry of [ 1025718-84-6 ]

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 :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	3.14
Log Po/w (WLOGP) :	4.33
Log Po/w (MLOGP) :	3.3
Log Po/w (SILICOS-IT) :	3.05
Consensus Log Po/w :	3.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.62
Solubility :	0.0583 mg/ml ; 0.000242 mol/l
Class :	Soluble
Log S (Ali) :	-3.23
Solubility :	0.14 mg/ml ; 0.000583 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.57
Solubility :	0.0653 mg/ml ; 0.000271 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 1025718-84-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 1025718-84-6 ]
Downstream synthetic route of [ 1025718-84-6 ]

[ 1025718-84-6 ] Synthesis Path-Upstream 1~1

1
[ 1025718-84-6 ]
[ 74-88-4 ]
[ 627527-23-5 ]

Yield	Reaction Conditions	Operation in experiment
1.98 g	With potassium carbonate In acetone at 60℃; for 3 h;	A mixture of 3-(tert-butyl)-5-methylphenol (1.5 g, 9.13 mmol), iodomethane (1.43 g, 10mmol) and K2C03 (1.89 g, 13.7 mmol) in acetone (20 mL) was heated with stuffing at 60 °C for3 hrs. The mixture was cooled down to rt and filtered. The filtrate was concentrated in vacuo to give crude 1-bromo-3-methoxy-5-(trifluoromethyl)benzene (1.98 g) which was used in the next step without further purification.

Reference： [1] Patent: WO2016/107832, 2016, A1, . Location in patent: Page/Page column 167

[ 1025718-84-6 ] Synthesis Path-Downstream 1~58

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%).

Reference： [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 ]

Reference： [1]Patent: WO2011/109799,2011,A1

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

Reference： [1]Patent: WO2011/109799,2011,A1

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

Reference： [1]Patent: WO2011/109799,2011,A1

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

Reference： [1]Patent: WO2011/109799,2011,A1

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

Reference： [1]Patent: WO2011/109799,2011,A1

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

Reference： [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.

Reference： [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).

Reference： [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

Reference： [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.

Reference： [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 ]

Reference： [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.

Reference： [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 ]