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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4-Chloro-2-(trifluoroacetyl)aniline HCl is an inhibitor of HIV-1 RT (HIV reverse transcriptase).
Synonyms: 4-Chloro-2-(trifluoroacetyl)aniline HCl
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Batch number can be found on the product's label following the word 'Batch'.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 173676-59-0 |
Formula : | C8H6Cl2F3NO |
M.W : | 260.04 |
SMILES Code : | FC(F)(F)C(C1=CC(Cl)=CC=C1N)=O.[H]Cl |
Synonyms : |
4-Chloro-2-(trifluoroacetyl)aniline HCl
|
MDL No. : | MFCD09263480 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In dimethoxyethane (DME);Heating / reflux; | 1 -f2-Amino-5-chlorophenyl)-2,2,2-1rifluoroethanone (8-3)6N Hydrochloric acid (6.0M, 257 mmol) was added to N-[4-chloro-2-(trifluoroacetyl)phenyl]-2,2-dimethylpropanamide (3.3 g, 10.7 mmol) in anhydrous dimethoxyethane (40 ml) at room temperature and mixture was heated to reflux conditions for two hours until no starting material was observed by LC/MS. After cooling reaction to 00C, reaction was basified to pH 9 by adding solid sodium bicarbonate in portions. Reaction was extracted with ethyl acetate (3x150ml), and EPO <DP n="38"/>combined organic extracts were dried over MgSO4 and Na2SO4. After filtering mixture, the collected filtrate was concentrated in vacuo to give a crude yellow solid. Flash chromatography of the crude solid on silica gel (0-25% ethyl acetate/hexanes) afforded l-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta 7.70 (m, IH), 7.32 (dd, J=2.4 and 9.2 Hz, IH), 6.68 (d, J= 8.8 Hz, IH), 6.46 (s, 2H). MS (Electrospray): m/z 223.9 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With sodium hydrogencarbonate; In water; at 20℃; for 0.05h;Inert atmosphere; Schlenk technique; | A hydrochloride-hydrate adduct of 2g (407 mg, 1.46 mmol) was placed in a 15-mL screw-capvial. To this, a saturated NaHCO3 aqueous solution (2.0 mL) was added, and the resulting mixturewas stirred at room temperature for 3 min. The aqueous phase was extracted with EtOAc (5 mL × 3).The combined organic layer was washed with brine (2 mL) and then dried over anhydrous sodiumsulfate (Na2SO4). Filtration and evaporation of the solvent left a residue, which was successivelypassed through a pad of silica gel using EtOAc to give analytically pure 2g in 99% yield (324 mg) as ayellow solid (m.p. 92-94 C). Compound 2g has already appeared in the literature [87], and itsspectral and analytical data are in good agreement with those reported. Accordingly, only the1H-NMR data are provided here. 1H-NMR (400 MHz, CDCl3) delta 6.47 (bs, 2H), 6.70 (d, J = 8.9 Hz, 1H),7.33 (dd, J = 9.0, 2.4 Hz, 1H), 7.66-7.75 (m, 1H). |
With sodium carbonate; In dimethoxyethane (DME);pH 9; | 1 -f2-Amino-5-chlorophenyl)-2,2,2-1rifluoroethanone (8-3)6N Hydrochloric acid (6.0M, 257 mmol) was added to N-[4-chloro-2-(trifluoroacetyl)phenyl]-2,2-dimethylpropanamide (3.3 g, 10.7 mmol) in anhydrous dimethoxyethane (40 ml) at room temperature and mixture was heated to reflux conditions for two hours until no starting material was observed by LC/MS. After cooling reaction to 00C, reaction was basified to pH 9 by adding solid sodium bicarbonate in portions. Reaction was extracted with ethyl acetate (3x150ml), and EPO <DP n="38"/>combined organic extracts were dried over MgSO4 and Na2SO4. After filtering mixture, the collected filtrate was concentrated in vacuo to give a crude yellow solid. Flash chromatography of the crude solid on silica gel (0-25% ethyl acetate/hexanes) afforded l-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone as a yellow solid. 1H NMR (CDCl3, 400 MHz) delta 7.70 (m, IH), 7.32 (dd, J=2.4 and 9.2 Hz, IH), 6.68 (d, J= 8.8 Hz, IH), 6.46 (s, 2H). MS (Electrospray): m/z 223.9 (M+). | |
With sodium hydrogencarbonate; In water; toluene; at 20℃;pH 7 - 8; | Example 1; Preparation of 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone (2): A solution of <strong>[173676-59-0]1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone hydrochloride</strong> hydrate (48.5 g, 174.4 mmol), 300 mL toluene, and 150 mL water was stirred at room temperature for 30 minutes. The pH of the solution was adjusted to 7-8 via the addition of saturated aqueous NaHCO3 solution. The resulting mixture was then separated, and the toluene layer was collected and evaporated to dryness to give 38.2 g 1-(2-amino-5-chlorophenyl)-2,2,2-trifluoroethanone (2) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Step 2: Synthesis of l-(2-amino-5-chlorophenyl)-2,2,2,-trifluoroethanone hydrochloride from 4-chloro-2-bromo phenyl pivalamide. (0120) To the mixture of Magnesium turnings (leq) and 2 vol of THF were added few particles of iodine for initiating and starting material i.e (4-chloro-2-bromophenyl)pivalamide (1 gr) at room temperature and waited for initiation. Slowly add starting material (dissolved in Ivol of THF) drop wise once initiation was started. Lithium chloride (0.25 mmol) was added to the reaction mixture after completion of addition and stirred for about 6hrs at room temperature. Cooled the reaction mixture to -15C and ethyl trifluoroacetate (1.4mmol) was added. Raised the temperature of the reaction mixture to 20C, maintained for about 30 mints and quenched the reaction mixture with ammonium chloride solution. Extracted the reaction mixture with MTBE and combined organic layers were concentrated under reduced pressure. To the crude compound thus obtained was added acetic acid (4 vol) and HC1 (2 vol). Slowly heated the reaction mixture to 75C and maintained the reaction mixture at the same temperature for about 4hrs. Cooled the reaction mixture to 0-5C for 2hrs, filtered and washed with Ivol of ethylacetate to afford 70% of title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
121 g | 1 liter of pressure reactor. To the kettle was added 127 g of 2,2,2-trifluoro-(2'-nitro-5'-chlorophenyl)ethanone, 250 g of ethyl acetate was added, 10 g of a palladium-carbon catalyst having a metal content of 5%. Pressure reactor with nitrogen replacement 3 times, and then converted to hydrogen 3 times, through the hydrogen to open the stirring reaction, hydrogen pressure maintained at less than 0.1-1.4MPa, temperature control 20-60 C, monitoring reaction. After the disappearance of raw materials pressure reactor to normal pressure, cooling to room temperature filtration, filter catalyst, 100 g of 36% hydrochloric acid was added directly to the filtrate and stirred for 30 minutes. The filtrate was dried to give 121 g of 4-chloro-2-(trifluoroacetyl)aniline hydrochloride hydrate in an amount of 99.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With indium(III) bromide; In chlorobenzene; at 110℃; under 760.051 Torr; for 24h;Inert atmosphere; Schlenk technique; | General procedure: InBr3 [(4.43 mg, 12.5 mumol), (13.3 mg, 37.5 mumol) or (39.0 mg, 110 mumol)] or InI3 (6.19mg, 12.5 mumol) was placed in a 20 mL Schlenk tube, which was heated at 80 C in vacuo for 15min. The tube was cooled down to room temperature and filled with argon or air. PhCl (0.20,0.30, 0.40, 0.50 or 1.7 mL) or o-C6H4Cl2 (0.20 mL) was added to the tube, and the mixture wasthen stirred at room temperature for 3 min. To this were added alkoxyheteroarenes 3 (0.250,0.300, 0.500, 0.625 or 5.50 mmol) and o-acylanilines 2 (0.250, 0.300 or 2.20 mmol) in the order,and the mixture was stirred at 70, 100, 110, 120, 130 or 170 C. After stirring for 3, 24 or 36 h,a saturated NaHCO3 aqueous solution (0.5 mL) was added at room temperature, and theresulting mixture was stirred for 20 min. The aqueous phase was extracted with EtOAc (5 mL× 3). The combined organic layer was washed with brine (1 mL) and then dried overanhydrous sodium sulfate (Na2SO4). Filtration and evaporation of the solvent followed bypurification gave product 4. Unless otherwise noted, the annulation reaction was performedaccording to the above procedure, and products 4 synthesized here were fully characterized by1H and 13C NMR spectroscopy and HRMS. Products 4 with fluorine atoms were characterizedadditionally by 19F NMR spectroscopy. |