[ CAS No. 72534-45-3 ]

Name: 72534-45-3|2-Amino-6-(trifluoromethyl)phenol|96%
Brand: Ambeed
SKU: A345799
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Product Details of [ 72534-45-3 ]

CAS No. :	72534-45-3	MDL No. :	MFCD08532490
Formula :	C₇H₆F₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	177.12 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 72534-45-3 ]

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 [ 72534-45-3 ]

* 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 [ 72534-45-3 ]

[ 72534-45-3 ] Synthesis Path-Downstream 1~19

2
[ 1548-62-5 ]
[ 7772-99-8 ]
[ 72534-45-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol;	a) Preparation of 3-trifluoromethyl-2-hydroxyaniline To the solution of <strong>[1548-62-5]2-trifluoromethyl-6-nitrophenol</strong> (4.2 g, 20.3 mmol) in ethanol (20 ml, Tin (II) chloride (22.9 g, 101 mmol) was added. The reaction mixture was stirred at reflux for about 4 hours, tThen it was cooled to room temperature. The NaHCO3 (aq) was added until pH=7 was obtained and then the mixture was extracted with ethyl acetate (3*). The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to give desired product (3.4 g, 94%). EI-MS m/z 178 (M+).
88%	In ethanol;	b) Preparation of 2-amino-6-trifluoromethylphenol A mixture of 6-trifluoromethyl-2-nitrophenol(1.84 g, 8.67 mmol) and tin (II) chloride (6.0 g, 26.2 mmol) in ethanol(150 mL) was heated at 80 C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2 Cl2) gave the desired product(1.35 g, 88%). 1 H NMR (CD3 OD): delta 6.93 (d, 1H), 6.82 (t, 1H), 6.78 (d, 1H).
88%	In ethanol;	b)Preparation of 2-amino-6-trifluoromethylphenol A mixture of 6-trifluoromethyl-2-nitrophenol(1.84 g, 8.67 mmol) and tin (II) chloride (6.0 g, 26.2 mmol) in ethanol(150 mL) was heated at 80 C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2 Cl2) gave the desired product(1.35 g, 88%). 1 H NMR (CD3 OD): d 6.93 (d, 1H), 6.82 (t, 1H), 6.78 (d, 1H).

Reference： [1]Patent: US6271261,2001,B1
[2]Patent: US5886044,1999,A
[3]Patent: US5780483,1998,A

3
[ 72534-45-3 ]
[ 182498-97-1 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane;	c) Preparation of N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl] urea N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl] urea was prepared from 2-amino-6-trifluoromethylphenol (280 mg, 1.60 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chloride/hexane(1/20) and filtering. (390 mg, 65%). 1 H NMR (CD3 OD): δ 7.99 (d, 1H), 7.60 (d, 1H), 7.58 (d, 1H), 7.34 (t, 1H), 7.30 (d, 1H), 7.00 (t, 1H), 6.96 (d, 1H).
	In hexane;	c)Preparation of N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl]urea N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl]urea was prepared from 2-amino-6-trifluoromethylphenol (280 mg, 1.60 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chloride/ hexane(1/20) and filtering. (390 mg, 65%). 1 H NMR (CD3 OD): d 7.99 (d, 1H), 7.60 (d, 1H), 7.58 (d, 1H), 7.34 (t, 1H), 7.30 (d, 1H), 7.00 (t, 1H), 6.96 (d, 1H).
	In hexane;	c) Preparation of N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl]urea N-[2-hydroxy-3-trifluoromethylphenyl]-N'-[2-bromophenyl]urea was prepared from 2-amino-6-trifluoromethylphenol (280 mg, 1.60 mmol) according to the procedure in General Method B. The product was purified by precipitation from methylene chloride/hexane (1/20) and filtering. (390 mg, 65%). 1H NMR (CD3OD): d 7.99 (d, 1H), 7.60 (d, 1H), 7.58 (d, 1H), 7.34 (t, 1H), 7.30 (d, 1H), 7.00 (t, 1H), 6.96 (d, 1H).

Reference： [1]Patent: US5886044,1999,A
[2]Patent: US5780483,1998,A
[3]Patent: US6262113,2001,B1

4
[ 72534-45-3 ]
[ 3173-56-6 ]
N-(2-Hydroxy-3-trifluoromethylphenyl)-N'-benzylurea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In N,N-dimethyl-formamide;	b) Preparation of N-(2-Hydroxy-3-trifluoromethylphenyl)-N'-benzylurea To a solution of benzylisocyanate (74.56 mg, 0.56 mmol) in DMF (1.0 ml), 2-hydroxy-3-trifluoromethylaniline (100 mg, 0.56 mmol) was added. The reaction mixture was stirred at 80 C. for 16 hours. Chromatography of the resulting liquid on silica gel gave desired product (140 mg, 80%). EI-MS m/z 311.1 (M+).

Reference： [1]Patent: US6271261,2001,B1

5
[ 72534-45-3 ]
[ 132741-19-6 ]
2-(4-bromophenyl)-8-(trifluoromethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20.0℃; for 3.0h;Cooling with ice;	Step B: 2-(4-bromophenyl)-8-(trifluoromethyl)-2H-benzo[b][l,4]oxazin-3(4H)-one To a solution of 2-amino-6-(trifluoromethyl) phenol (5.13 g, 29 mmol) in DMF (100 mL) was added K2CO3 (16 g, 116 mmol). The mixture was cooled by ice-water bath, to which 2- bromo-2-(4-bromophenyl)acetyl chloride (10.8 g, 35 mmol) was added dropwisely. Then the reaction was stirred at room temperature for 3 h. TLC (petroleum ether: EtOAc= 5: 1) showed that the reaction was complete. The resulting mixture was quenched and diluted by H20 (400 mL), extracted with DCM (300 mL3). The combined organic layers were washed by brine (300 mL3), dried over a2S04, filtered and concentrated in vacuo. The residue was purified by column chromatography (EtOAc in petroleum ether: 0-20%) to give 2-(4-bromophenyl)-8- (trifluoromethyl)-2H-benzo[b][l,4]oxazin-3(4H)-one as a solid, which was used for next step without any purification. XH NMR (CDC13, 400 MHz): δ 8.41 (br.s, 1 H), 7.48 (d, J= 8.4 Hz, 2H), 7.33 (d, J= 8.4 Hz, 2H), 7.26(d, J= 7.6 Hz, 1H), 7.04 (t, J= 8.0 Hz, 1H), 6.97 (d, J= 7.6 Hz, 1H), 5.78 (s, 1H).

Reference： [1]Patent: WO2016/49099,2016,A1 .Location in patent: Page/Page column 151-152

6
[ 72534-45-3 ]
2-(4-bromophenyl)-8-(trifluoromethyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine [ No CAS ]