[ CAS No. 193090-60-7 ]

Name: 193090-60-7|5-Amino-4-bromo-2-fluorobenzotrifluoride|98%
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Quality Control of [ 193090-60-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 193090-60-7 ]

CAS No. :	193090-60-7	MDL No. :	MFCD04973755
Formula :	C₇H₄BrF₄N	Boiling Point :	253.7°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	258.01 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 193090-60-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P262-P280	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 193090-60-7 ]

Downstream synthetic route of [ 193090-60-7 ]

[ 193090-60-7 ] Synthesis Path-Downstream 1~14

1
[ 193090-60-7 ]
[ 1147550-11-5 ]
[ 1355240-98-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: ammonium thiocyanate With benzoyl chloride In acetone for 0.25h; Reflux; Stage #2: 2-bromo-4-fluoro-5-(trifluoromethyl)aniline In acetone at 40℃; for 1.5h; Reflux; Stage #3: With sodium hydroxide at 60℃; for 2h;	Benzoyl chloride (1.53 g, 10.8 mmol) was added to a solution of ammonium thiocyanate (0.94 g, 12.4 mmol) in acetone (17 mL) over 5 minutes and the mixture was refluxed for 15 minutes. 2-Bromo-4-fluoro-5-(trifiuoromethyl)aniline (2.0 g, 7.7 mmol) in acetone (14 mL) was added to the mixture at 40 and refluxing was continued for 90 minutes. The hot solution was poured over ice (100 mL) and the mixture was stirred for 5 minutes until a precipitate formed, which was collected by filtration and washed with 50% methanol in water (30 mL). To the precipitate was added a 5% sodium hydroxide solution (100 mL) and the suspension was stirred for 2 hours at 80. The mixture was allowed to cool down to room temperature and extracted with diethyl ether and ethylacetate. The combined organic extracts were washed with brine and concentrated under reduced pressure to yield 2.37 g (96%) 1-[2-bromo-4-fluoro-5- (trifluoromethyl)phenyi]thiourea:1H NMR (400 MHz, DMSO-cfe) δ = 7.45 (br., 2H), 7.96 (d, 1 H), 8.01 (d, 1 H), 9.42 (s, 1 H) ppm.

Reference： [1]Current Patent Assignee: BAYER AG - WO2012/7510, 2012, A1 Location in patent: Page/Page column 44

2
[ 193090-60-7 ]
[ 1355240-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: benzoyl chloride / acetone / 0.25 h / Reflux 1.2: 1.5 h / 40 °C / Reflux 1.3: 2 h / 60 °C 2.1: caesium carbonate; copper(l) iodide; rac-Pro-OH / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere 2.2: 0.08 h / Cooling with ice; Saturated solution 3.1: tert.-butylnitrite; copper dichloride / acetonitrile / 4 h / 0 - 20 °C 4.1: caesium carbonate / N,N-dimethyl-formamide; acetonitrile / 2.75 h / 75 °C

Reference： [1]Current Patent Assignee: BAYER AG - WO2012/7510, 2012, A1

3
[ 193090-60-7 ]
[ 1355241-00-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: benzoyl chloride / acetone / 0.25 h / Reflux 1.2: 1.5 h / 40 °C / Reflux 1.3: 2 h / 60 °C 2.1: caesium carbonate; copper(l) iodide; rac-Pro-OH / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere 2.2: 0.08 h / Cooling with ice; Saturated solution

Reference： [1]Current Patent Assignee: BAYER AG - WO2012/7510, 2012, A1

4
[ 193090-60-7 ]
[ 1355241-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: benzoyl chloride / acetone / 0.25 h / Reflux 1.2: 1.5 h / 40 °C / Reflux 1.3: 2 h / 60 °C 2.1: caesium carbonate; copper(l) iodide; rac-Pro-OH / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere 2.2: 0.08 h / Cooling with ice; Saturated solution 3.1: tert.-butylnitrite; copper dichloride / acetonitrile / 4 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: BAYER AG - WO2012/7510, 2012, A1

5
[ 865245-32-5 ]
[ 193090-60-7 ]
tert-butyl 6-(2-amino-5-fluoro-4-(trifluoromethyl)phenyl)-3,4-dihydropyridine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In 1,4-dioxane; water at 80℃; for 5h; Inert atmosphere;	24.1 Step 1: tert-butyl 6-(2-amino-5-fluoro-4-(trifluoromethyl)phenyl)-3,4-dihydropyridine-1-carboxylate : A mixture of 2-bromo-4-fluoro-5-(trifluoromethyl)aniline (224 mg, 842 pmol, 97% purity), tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydropyridine-1-carboxylate (283 mg, 842 pmol, 92% purity), K3PC>4(s) (360 mg, 1.70 mmol), PdCl2(AmPhos)2 (57 mg, 81 pmol) in dioxane (3 ml) and water (0.75 ml) was sparged with N2 for 10 min, and then heated at 80 °C for 5 h. The reaction mixture was allowed to cool to RT and was filtered through Celite, washing with EtOAc (10 ml), and the filtrate concentrated in vacuo. The crude product was purified by chromatography on silica gel (12 g cartridge, 0-30% EtOAc/isohexane) to afford the title compound (197 g, 0.46 mmol, 55% yield, 85% purity) as an orange oil. UPLC-MS (Method 5): m/z 261.2 (M+H-Boc)+, at 0.77 min.

Reference： [1]Current Patent Assignee: GREY WOLF THERAPEUTICS - WO2021/94763, 2021, A1 Location in patent: Page/Page column 110-111

6
[ 193090-60-7 ]
tert-butyl 6-(2-((2-cyclopropyl-5-(methoxycarbonyl)phenyl)sulfonamido)-5-fluoro-4-(trifluoromethyl)phenyl)-3,4-dihydropyridine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / 1,4-dioxane; water / 5 h / 80 °C / Inert atmosphere 2: pyridine / 91 h / 20 °C

Reference： [1]Current Patent Assignee: GREY WOLF THERAPEUTICS - WO2021/94763, 2021, A1

7
[ 193090-60-7 ]
methyl 4-cyclopropyl-3-(N-(4-fluoro-2-(piperidin-2-yl)-5-(trifluoromethyl)phenyl)sulfamoyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) / 1,4-dioxane; water / 5 h / 80 °C / Inert atmosphere 2.1: pyridine / 91 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 3.2: 1 h / 20 °C

Reference： [1]Current Patent Assignee: GREY WOLF THERAPEUTICS - WO2021/94763, 2021, A1

8
[ 2357-47-3 ]
[ 193090-60-7 ]

Yield	Reaction Conditions	Operation in experiment
	With NBS In dichloromethane at 20℃; for 16h; Inert atmosphere;	84 2-bromo-4-fluoro-5-(trifluoromethyl)aniline To a solution of 4-fluoro-3- (trifluoromethyl)aniline (25 g, 139.6 mmol) in DCM (80 mL) was added NBS (24.8 g, 139.6 mmol) in DCM (160 mL). The mixture was stirred at 20 °C for 16 h. The reaction mixture was diluted with sat. aq. NaHCO3 (200 mL) and extracted with DCM (3 × 100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography.

Reference： [1]Current Patent Assignee: DENALI THERAPEUTICS INC - WO2022/109268, 2022, A1 Location in patent: Paragraph 0209; 0446

9
[ 193090-60-7 ]
methyl 2-bromo-5-fluoro-4-(trifluoromethyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1,1'-bis(diphenylphosphanyl)ferrocene; palladium diacetate; triethylamine / dimethyl sulfoxide; methanol / 16 h / 80 °C / 2585.81 Torr / Inert atmosphere 2: copper(II) bromide; tert.-butylnitrite; copper (II) bromide / acetonitrile / 2 h / 65 °C / Inert atmosphere