[ CAS No. 454-82-0 ] {[proInfo.proName]}

Name: 454-82-0|2-Amino-5-(trifluoromethyl)phenol|95%
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Quality Control of [ 454-82-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 454-82-0 ]

Product Details of [ 454-82-0 ]

CAS No. :	454-82-0	MDL No. :	MFCD08056279
Formula :	C₇H₆F₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ILZRAAUVZAXXKZ-UHFFFAOYSA-N
M.W :	177.12	Pubchem ID :	15524277
Synonyms :

Calculated chemistry of [ 454-82-0 ]

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 :	2.0
Molar Refractivity :	37.87
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.16
Log Po/w (XLOGP3) :	1.77
Log Po/w (WLOGP) :	3.15
Log Po/w (MLOGP) :	1.91
Log Po/w (SILICOS-IT) :	1.65
Consensus Log Po/w :	1.93

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.36
Solubility :	0.778 mg/ml ; 0.00439 mol/l
Class :	Soluble
Log S (Ali) :	-2.36
Solubility :	0.775 mg/ml ; 0.00437 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.35
Solubility :	0.797 mg/ml ; 0.0045 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.01

Safety of [ 454-82-0 ]

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

Application In Synthesis of [ 454-82-0 ]

* 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 [ 454-82-0 ]
Downstream synthetic route of [ 454-82-0 ]

[ 454-82-0 ] Synthesis Path-Upstream 1~5

1
[ 454-82-0 ]
[ 90800-42-3 ]

Reference： [1] Journal of the Chemical Society, 1954, p. 3846,3849

2
[ 402-17-5 ]
[ 454-82-0 ]

Reference： [1] Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9076 - 9082
[2] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 108 - 119
[3] Journal of the Chemical Society, 1954, p. 3846,3849
[4] Patent: US5886044, 1999, A,
[5] Patent: US5780483, 1998, A,
[6] Patent: US6262113, 2001, B1,

3
[ 75-63-8 ]
[ 95-55-6 ]
[ 454-82-0 ]
[ 106877-48-9 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 8, p. 2293 - 2299

4
[ 98-17-9 ]
[ 454-82-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 108 - 119

5
[ 402-14-2 ]
[ 454-82-0 ]

Reference： [1] Journal of the Chemical Society, 1954, p. 3846,3849

[ 454-82-0 ] Synthesis Path-Downstream 1~79

1
[ 402-17-5 ]
[ 454-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	With stannous chloride; sodium hydrogencarbonate; In ethanol;	b) Preparation of 2-amino-5-trifluoromethylphenol 2-Amino-5-trifluoromethylphenol was prepared by treating 2-nitro-5-trifluoromethylphenol (500 mg, 2.41 mmol) with a solution of SnCl2 (3.5 g, mmol) in EtOH at 23 C. for 12 h. The mixture was concentrated to 50 mL and adjusted to pH7 using saturated sodium bicarbonate. The reaction mixture was partitioned between H2 O and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting colorless oil(370 mg, 87%) was used without further purification. 1H NMR (CDCl3): 7.6 (s, 1H), 7.39(d, 1H, J=8.5 Hz), 7.08(d, 1H, J=8.5 Hz)
	With stannous chloride; sodium hydrogencarbonate; In ethanol;	b)Preparation of 2-amino-5-trifluoromethylphenol 2-Amino-5-trifluoromethylphenol was prepared by treating 2-nitro-5-trifluoromethylphenol (500 mg, 2.41 mmol) with a solution of SnCl2 (3.5g, mmol) in EtOH at 23 C. for 12 h. The mixture was concentrated to 50 mL and adjusted to pH 7 using saturated sodium bicarbonate. The reaction mixture was partitioned between H2 O and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting colorless oil(370 mg, 87%) was used without further purification. 1H NMR (CDCl3): 7.6 (s, 1H), 7.39(d, 1H, J =8.5 Hz), 7.08(d, 1H, J=8.5 Hz)
	With sodium hydrogencarbonate; In ethanol;	b) Preparation of 2-amino-5-trifluoromethylphenol 2-Amino-5-trifluoromethylphenol was prepared by treating 2-nitro-5-trifluoromethylphenol (500 mg, 2.41 (M mol) with a solution of SnCl2(3.5 g, mmol) in EtOH at 23 C for 12 h. The mixture was concentrated to 50 mL and adjusted to pH 7 using saturated sodium bicarbonate. The reaction mixture was partitioned between H2O and EtOAc. The aqueous layer was separated and extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The resulting colorless oil(370 mg, 87%) was used without further purification. 1H NMR (CDCl3): 7.6 (s, 1H), 7.39(d, 1H, J=8.5 Hz), 7.08(d, 1H, J=8.5 Hz)

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 9076 - 9082
[2]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119
[3]Journal of the Chemical Society,1954,p. 3846,3849
[4]Patent: US5886044,1999,A
[5]Patent: US5780483,1998,A
[6]Patent: US6262113,2001,B1

2
[ 454-82-0 ]
[ 56-81-5 ]
[ 321-70-0 ]

Reference： [1]Journal of the Chemical Society,1954,p. 3846,3849

3
[ 75-63-8 ]
[ 95-55-6 ]
[ 454-82-0 ]
[ 106877-48-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 2293 - 2299

4
[ 454-82-0 ]
[ 6531-08-4 ]
[ 765303-32-0 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4627 - 4630

5
[ 15761-39-4 ]
[ 454-82-0 ]
C₁₇H₂₁F₃N₂O₄ [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 10253 - 10259

6
[ 454-82-0 ]
pyrrolidine-2-carboxylic acid (2'-hydroxy-4'-trifluoromethyl-phenyl)-amide trifluoroacetate [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 10253 - 10259

7
[ 454-82-0 ]
[ 765303-33-1 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4627 - 4630

8
[ 454-82-0 ]
3-chloro-9-trifluoromethyl-6-(4-iodobutyl)pyridazino[3,4-b][1,5]benzoxazepin-5(6H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4627 - 4630

9
[ 454-82-0 ]
3-chloro-9-trifluoromethyl-6-[3-(4-phenylpiperazin-1-yl)propyl]pyridazino[3,4-b][1,5]benzoxazepin-5(6H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4627 - 4630

10
[ 454-82-0 ]
6-[3-(4-benzylpiperazin-1-yl)propyl]-3-chloro-9-trifluoromethylpyridazino[3,4-b][1,5]benzoxazepin-5(6H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4627 - 4630

11
[ 402-14-2 ]
[ 454-82-0 ]

Reference： [1]Journal of the Chemical Society,1954,p. 3846,3849

12
[ 454-82-0 ]
[ 90800-42-3 ]

Reference： [1]Journal of the Chemical Society,1954,p. 3846,3849

13
[ 454-82-0 ]
[ 391-49-1 ]

Reference： [1]Journal of the Chemical Society,1954,p. 3846,3849

14
[ 454-82-0 ]
[ 442-79-5 ]

Reference： [1]Journal of the Chemical Society,1954,p. 3846,3849

16
[ 454-82-0 ]
[ 103-71-9 ]
N-[2-Hydroxy-4-(trifluoromethyl)phenyl]-N'-phenyl urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		c)Preparation of N -[2-hydroxy-4-(trifluoromethyl) phenyl]-N'-phenyl urea N -[2-Hydroxy-4-(trifluoromethyl) phenyl]-N'-phenyl urea was prepared from <strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong> (150 mg, 1.09 mmol) and phenyl isocyanate (1.09 mmol) according to the procedure in General method A. The product was purified by precipitation from methylene chloride and filtering to afford the titled compound (230 mg, 87%). mp: C.; 1H NMR (DMSO-d6): d 9.45 (s, 1H, NH), 8.50 (s, 1H, NH), 8.31 (d, 1H, J=10.0 Hz), 7.45 (d, 2H, J=10.0 Hz), 7.29 (t, 2H, J=6.67 Hz), 7.10 (m, 2H), 6.99 (t, 1H, J=6.67 Hz). EI-MS m/z 296 (M+). Anal. (C14H11N2O2F3)C, H, N.

Reference： [1]Patent: US6262113,2001,B1

17
[ 17337-13-2 ]
[ 454-82-0 ]
N-(4-Trifluoromethyl-2-hydroxy phenyl)-N'-(2-phenyl phenyl)-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		Example 34 Synthesis of N-(2-hydroxy 4-trifluoromethyl phenyl) N'-(2-phenyl phenyl) urea The urea was prepared from 2-hydroxy 4-trifluoromethyl aniline (example 7a, 0.171 g, 1 mmol)) and 2-phenyl phenyl isocyanate by general Method B. It was purified by dilution with methylene chloride and precipitation with hexane. Filtering afforded the desired compound (0.24 g, 64%). EI-MS m/z 373 (M+H)+

Reference： [1]Patent: US6262113,2001,B1

18
[ 454-82-0 ]
[ 1592-00-3 ]
N-(4-Trifluoromethyl-2-hydroxy phenyl)-N'-(2-bromo phenyl)-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		Example 32 Synthesis of N-(2-hydroxy 4-trifluoromethyl phenyl) N'-(2-bromo phenyl) urea The urea was prepared from 2-hydroxy 4-trifluoromethyl aniline (example 7a, 0.171 g, I mmol) and 2-bromo phenyl isocyanate (1 mmol) by general Method B. It was purified by dilution with methylene chloride and precipitation with hexane. Filtering afforded the desired compound (0.25 g, 54%). EI-MS m/z 375 (M+H)+

Reference： [1]Patent: US6262113,2001,B1

19
[ 1020727-12-1 ]
[ 454-82-0 ]
[ 865203-70-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In ethanol; for 1h;Heating / reflux;	5. 2-[2-Chloro-3-nitro-7-(3-trifluoromethyl-pyridin-2-yl)-[1,8]naphthyridine-4-ylamino]-5-trifluoromethyl-1-phenol Heat a solution of 2,4-dichloro-3-nitro-7-(3-trifluoromethyl-pyridin-2-yl)-[1,8]naphthyridine (65 mg), 2-amino-5-(trifluoromethyl)-phenyl (30 mg), sodium acetate (17 mg) in EtOH (2 mL) to reflux for 1 hour. Cool, add water (2 mL), collect the precipitate by filtration and air-dry to give the title compound.

Reference： [1]Patent: US2007/203133,2007,A1 .Location in patent: Page/Page column 26

20
[ 55-22-1 ]
[ 454-82-0 ]
[ 1192020-97-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 80℃; for 3h;	A mixture of 1.30 g of <strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong>, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80C for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of-(2-hydroxy-4-trifluoromethylphenyl)isonicotinamide. [Show Image] 1H-NMR (DMSO-d6) delta: 8.82-8.76 (m, 2H), 7.98-7.93 (m, 1H), 7.89-7,85 (m, 2H), 7.23-7.17 (m, 2H)
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 80℃; for 3h;	Reference Production Example 9To 7.5 g of 3-trifluoromethylphenol, 9 ml of 70% nitric acid was added dropwise at room temperature and the reaction mixture was stirred for one hour. The reaction mixture was poured into an ice-cooled saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate twice. The combined organic layers washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.56 g of 2-nitro-5-trifluoromethylphenol.1H-NMR (CDCl3) delta: 10.59 (s, 1H), 8.25 (d, J=8.8 Hz, 1H), 7.48-7.46 (m, 1H), 7.27-7.23 (m, 1H)<strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong> was obtained according to the same manner as that of Reference Production Example 1, using 2-nitro-5-trifluoromethylphenol instead of 4-propyl-2-nitrophenol.1H-NMR (CDCl3+DMSO-d6) delta: 9.03 (br s, 1H), 7.01 (d, J=1.8 Hz, 1H), 6.95-6.91 (m, 1H), 6.71-6.66 (m, 1H), 4.13 (br s, 2H)A mixture of 1.30 g of <strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong>, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80 C. for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of N-(2-hydroxy-4-trifluoromethylphenyl)isonicotinamide.1H-NMR (DMSO-d6) delta: 8.82-8.76 (m, 2H), 7.98-7.93 (m, 1H), 7.89-7.85 (m, 2H), 7.23-7.17 (m, 2H)
	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In pyridine; at 80℃; for 3h;	A mixture of 1.30 g of <strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong>, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80C for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of N- (2-hydroxy-4-trifluoromethylphenyl)isonicotinamide.-NMR (DMSO-d6) delta: 8.82-8.76 (m, 2H), 7.98-7.93 (m, 1H), 7.89-7.85 (m, 2H), 7.23-7.17 (m, 2H)

	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 80℃; for 3h;	A mixture of 1.30 g of <strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong>, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80C for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of N- (2-hydroxy-4-trifluoromethylphenyl)isonicotinamide.1H-NMR (DMSO-d6) delta: 8.82-8.76 (m, 2H), 7.98-7.93 (m, 1H), 7.89-7.85 (m, 2H), 7.23-7.17 (m, 2H)
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 80℃; for 3h;	A mixture of 1.30 g of <strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong>, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80C for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of N- (2-hydroxy-4-trifluoromethylphenyl)isonicotinamide.-NMR (DMSO-d6) 6: 8.82-8.76 (m, 2H), 7.98-7.93 (m, 1H), 7.89-7.85 (m, 2H), 7.23-7.17 (m, 2H)
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 80℃; for 3h;	A mixture of 1.30 g of <strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong>, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80C for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of N- (2-hydroxy-4-trifluoromethylphenyl)isonicotinamide.-NMR (DMSO-d6) delta: 8.82-8.76 (m, 2H), 7.98-7.93 (m, 1H), 7.89-7.85 (m, 2H), 7.23-7.17 (m, 2H)
	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 80℃; for 3h;	A mixture of 1.30 g of <strong>[454-82-0]2-amino-5-trifluoromethylphenol</strong>, 0.9 g of isonicotinic acid, 1.83 g of WSC and 15 ml of pyridine was stirred while heating at 80C for three hours. The mixture was cooled to room temperature, and then water was poured. Precipitated solid was filtered and washed with water, and then dried under reduced pressure to give 1.5 g of N- (2-hydroxy-4-trifluoromethylphenyl)isonicotinamide.-NMR (DMSO-d6) delta: 8.82-8.76 (m, 2H), 7.98-7.93 (m, 1H), 7.89-7.85 (m, 2H), 7.23-7.17 (m, 2H)

Reference： [1]Patent: EP2274983,2011,A1 .Location in patent: Page/Page column 123
[2]Patent: US2011/39843,2011,A1 .Location in patent: Page/Page column 77
[3]Patent: WO2011/40629,2011,A1 .Location in patent: Page/Page column 204-205
[4]Patent: WO2011/49220,2011,A1 .Location in patent: Page/Page column 203-204
[5]Patent: WO2011/49221,2011,A1 .Location in patent: Page/Page column 205
[6]Patent: WO2011/49223,2011,A1 .Location in patent: Page/Page column 203-204
[7]Patent: WO2011/49222,2011,A1 .Location in patent: Page/Page column 208

21
[ 98-17-9 ]
[ 454-82-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119

22
[ 55-22-1 ]
[ 454-82-0 ]
[ 1192019-02-5 ]

Reference： [1]Patent: WO2011/40629,2011,A1
[2]Patent: WO2011/49223,2011,A1
[3]Patent: US2011/39843,2011,A1

23
[ 454-82-0 ]
[ 78-94-4 ]
[ 1333317-64-8 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 9076 - 9082

24
[ 5607-64-7 ]
[ 454-82-0 ]
[ 1413929-86-8 ]
[ 1413930-03-6 ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119

25
[ 5607-64-7 ]
[ 454-82-0 ]
[ 1413929-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In diethyl ether; at 20℃; for 1h;	General procedure: First, 100 mL of an ether solution containing 2.7 mmol of substituted 2-methoxybenzoyl chloride (2) and an equimolar amount of TEA was added drop wise at r.t. (1.5 h) into 40 mL of a stirred ether solution containing 2.7 mmol of substituted 2-aminophenol (5). After the addition, the mixture was stirred for 1 h at r.t. and then extracted with a 5% solution of HCl (50 mL), with a 5% solution of NaHCO3 (50 mL) and with water (50 mL). The organic phase was dried with Na2SO4 and purified using column chromatography and crystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119

26
[ 454-82-0 ]
[ 29568-33-0 ]
[ 1413929-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In diethyl ether; at 20℃; for 1h;	General procedure: First, 100 mL of an ether solution containing 2.7 mmol of substituted 2-methoxybenzoyl chloride (2) and an equimolar amount of TEA was added drop wise at r.t. (1.5 h) into 40 mL of a stirred ether solution containing 2.7 mmol of substituted 2-aminophenol (5). After the addition, the mixture was stirred for 1 h at r.t. and then extracted with a 5% solution of HCl (50 mL), with a 5% solution of NaHCO3 (50 mL) and with water (50 mL). The organic phase was dried with Na2SO4 and purified using column chromatography and crystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119

27
[ 454-82-0 ]
[ 29568-33-0 ]
[ 1413929-93-7 ]
[ 1413930-09-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 56,p. 108 - 119

28
[ 454-82-0 ]
2-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)-6-(trifluoromethyl)benzo[d]oxazole [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 120 - 123

29
[ 454-82-0 ]
2-(2-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)ethoxy)-6-(trifluoromethyl)benzo[d]oxazole [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 120 - 123

30
[ 454-82-0 ]
2-(3-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy)-6-(trifluoromethyl)benzo[d]oxazole [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 120 - 123

31
[ 454-82-0 ]
2-(4-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)butoxy)-6-(trifluoromethyl)benzo[d]oxazole [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 120 - 123

32
[ 454-82-0 ]
2-chloro-6-(trifluoromethyl)benzo[d]oxazole [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 120 - 123

33
[ 75-15-0 ]
[ 454-82-0 ]
6-(trifluoromethyl)benzo[d]oxazole-2-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In ethanol; water; for 4.25h;Reflux;	General procedure: Potassium hydroxide (46 mmol), ethanol (25 mL) and water (10 mL) were added to a dried round-bottomed flask sequentially, followed by the dropwise addition of CS2 (25 mmol), after 15 min, (un)substituted 2-aminophenol (23 mmol) was added, then the resulting solution was heated to reflux for 4 h. The reaction solution was acidified to pH~4 with dilute hydrochloric acid and then poured into water, extracted with ethyl acetate, the organic phase was washed with brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and the residue was purified via silica gel column chromatography to obtain the intermediate the (un)substituted 2-mercaptobenzoxazole as a yellow solid. Then, the (un)substituted 2-mercaptobenzoxazole (5.5 mmol) was refluxed in SOCl2 (15 mL) for 2 h, excessive SOCl2 was removed under reduced pressure to give (un)substituted 2-chlorobenzoxazole as a yellow solid which was used in next reaction without further purification. Finally, 60 % of NaH (1.0 mmol) was added into a solution of 3,3-dichloroallyloxyphe-noxy intermediates (1.0 mmol) in THF (5 mL), after 2 h, (un)substituted 2-chloro-benzoxazole (1.0 mmol) was added, the reaction mixture was stirred for another 5 h at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with saturated sodium bicarbonate, brine, dried over anhydrous magnesium sulfate, concentrated and the residue was purified via silica gel column chromatography to afford the title compounds.

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 156,p. 120 - 123

34
[ 454-82-0 ]
2-oxo-N-(4-phenylbutyl)-6-(trifluoromethyl)-1,3-benzoxazole-3-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

35
[ 454-82-0 ]
[ 530-62-1 ]
6-(trifluoromethyl)-3H-1,3-benzoxazol-2-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9258 - 9272

36
(2-hydroxynaphthalen-1-yl)boronic acid [ No CAS ]
[ 454-82-0 ]
[ 84761-77-3 ]
(R)-1-(2-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)phenyl)naphthalen-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

37
[ 259209-21-7 ]
[ 1344713-92-3 ]
[ 454-82-0 ]
(R)-2'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-5,6'-dimethyl-[1,1'-biphenyl]-2-ol [ No CAS ]
2'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-5,6'-dimethyl-[1,1'-biphenyl]-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

38
[ 1344713-92-3 ]
[ 89488-25-5 ]
[ 454-82-0 ]
(R)-5-chloro-2'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-6'-methyl-[1,1'-biphenyl]-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

39
[ 259209-22-8 ]
[ 1344713-92-3 ]
[ 454-82-0 ]
(R)-2'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-3,6'-dimethyl-[1,1'-biphenyl]-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

40
2-(2-hydroxynaphthalen-1-yl)-3-methylbenzaldehyde [ No CAS ]
[ 454-82-0 ]
(R)-1-(2-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-6-methylphenyl)naphthalen-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

41
2-(2-hydroxynaphthalen-1-yl)-3-methylbenzaldehyde [ No CAS ]
[ 454-82-0 ]
(R)-1-(2-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-6-methylphenyl)naphthalen-2-ol [ No CAS ]
1-(2-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-6-methylphenyl)naphthalen-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5
[2]Organic Letters,2018,vol. 20,p. 6284 - 6288

42
[ 89466-08-0 ]
C₁₁H₁₁F₃O₄S [ No CAS ]
[ 454-82-0 ]
(R)-2'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-6'-isopropyl-[1,1'-biphenyl]-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

43
[ 1426547-43-4 ]
[ 89466-08-0 ]
[ 454-82-0 ]
(R)-6'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-2',3'-dimethyl-[1,1'-biphenyl]-2-ol [ No CAS ]
6'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-2',3'-dimethyl-[1,1'-biphenyl]-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

44
[ 89466-08-0 ]
[ 454-82-0 ]
[ 197015-45-5 ]
(R)-2-(((1-(2-hydroxyphenyl)naphthalen-2-yl)methyl)amino)-5-(trifluoromethyl)phenol [ No CAS ]
2-(((1-(2-hydroxyphenyl)naphthalen-2-yl)methyl)amino)-5-(trifluoromethyl)phenol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

45
[ 1426547-60-5 ]
[ 89466-08-0 ]
[ 454-82-0 ]
(R)-2-(((3-(2-hydroxyphenyl)-4-methylnaphthalen-2-yl)methyl)amino)-5-(trifluoromethyl)phenol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

46
[ 1344713-92-3 ]
[ 89466-08-0 ]
[ 454-82-0 ]
(R)-2'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-6'-methyl-[1,1'-biphenyl]-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

47
10-chloro-6H-benzo[c]chromen-6-ol [ No CAS ]
[ 454-82-0 ]
(S)-2'-chloro-6'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-[1,1'-biphenyl]-2-ol [ No CAS ]
2'-chloro-6'-(((2-hydroxy-4-(trifluoromethyl)phenyl)amino)methyl)-[1,1'-biphenyl]-2-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11642 - 11646
Angew. Chem.,2016,vol. 128,p. 11814 - 11818,5

48
[ 454-82-0 ]
2,2,4-trimethyl-7-(trifluoromethyl)-1,4-benzoxazin-3-one [ No CAS ]