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CAS No. : | 22179-86-8 | MDL No. : | MFCD07776359 |
Formula : | C8H7F3N2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 204.15 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H312-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
100% | With hydroxylamine In ethanol; lithium hydroxide monohydrate Reflux; | |
100% | With hydroxylamine In ethanol; lithium hydroxide monohydrate for 8h; Reflux; | 1.82 4-(Trifluoromethyl)benzonitrile (1.0 g, 5.84 mmol) was reacted with NH2OH (0.37 mL, 6.13 mmol, aq.50%) in EtOH (6 mL) for 8 h as per General Procedure 1 Method 1 to provide N'-hydroxy-4-(trifluoromethyl)benzimidamide in 100% yield (1.19 g). |
99% | With hydroxyamino hydrochloride; triethylamine In ethanol for 3h; Reflux; Schlenk technique; Inert atmosphere; | 14 4-Trifluoromethyl-N-hydroxybenzamidine (11) A mixture of 4-trifluoromethylbenzonitrile 10 (0.350 g, 2.04 mmol), hydroxylamine hydrochloride (0.213 g, 3.07 mmol) and triethylamine (0.44 mL, 3.24 mmol) in ethanol (4 mL) was refluxed for 3 h. After the completion of the reaction, the solvent was evaporated the crude residue was dissolved in dichloromethane and washed with water and brine once. The organic layer was dried over magnesium sulfate, filtered and evaporated to give 11 as white solid (0.406 g, 99%); 1H NMR (300 MHz, Chloroform-d): δ 4.88 (br s, 2NH), 7.23 (s, 1H), 7.67 (d, J = 8.1 Hz, 2H), 7.76 (d, J = 8.1 Hz, 2H). The analytical data was consistent with literature data. 22 |
99% | With hydroxyamino hydrochloride; triethylamine In ethanol at 50℃; for 5h; | 116A Example 116A N'-hydroxy-4-(trifluoromethyl)benzenecarboximidamide To a solution of 4-(trifluoromethyl)benzonitril (5 g, 29.22 mmol) in 148 ml ethanol was added hydroxylammonium chloride (3.05 g, 43.83 mmol) and triethylamine (3.84 g, 37.98 mmol) and then the reaction mixture was 5 h at 50 °C. After cooling to RT, the solvent was evaporated and the crude was solved in ethyl acetate and extracted with water and brine solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (5.93 g, 99% of theory). LC-MS (method 2B): RT = 1.86 min, m/z = 205 (M+H)+ |
98% | With hydroxyamino hydrochloride; triethylamine In methanol at 20℃; Reflux; | 5 5.1.1. General procedure for the synthesis of N'-hydroxybenzimidamides 2a-2k General procedure: A solution of the appropriate cyanophenyl 1a-1k (0.1 mol), hydroxylamine hydrochloride (0.2 mol), and TEA (0.2 mol) in methanol was left under stirring at room temperature for 1 h, then heated under reflux until the disappearance of the starting materials (TLC analysis). After cooling, the solvent was evaporated to dryness under reduced pressure to give the crude, which was dissolved in ethyl acetate (400 mL) and washed with brine (3 100 mL) and dried with Na2SO4. The ethyl acetate was evaporated under reduced pressure to yield the compounds 2a-2k. |
98% | With hydroxyamino hydrochloride; triethylamine In methanol at 20 - 65℃; | 5 5.1.1 General procedure for the synthesis of N'-hydroxybenzimidamides 2a-2j General procedure: A solution of the appropriate cyanophenyl 1a-1j (0.1mol), hydroxylamine hydrochloride (0.2 mol), and TEA (0.2 mol) in methanol was stirred at room temperature for 1 h, then heated under reflux until the disappearance of the starting materials (TLC analysis). After cooling, the solvent was evaporated to dryness under reduced pressure to give the crude, which was dissolved in ethyl acetate (400 mL) and washed with brine (3×100 mL) and dried with Na2SO4. Ethyl acetate was evaporated under reduced pressure to yield the compounds 2a-2j. |
96% | With hydroxyamino hydrochloride; triethylamine In methanol at 20℃; for 0.5h; | 7 Embodiment 7: to the trifluoromethyl benzamide oxime (u) preparation of The trifluoromethyl methyl benzonitrile (3.4 g, 20.0 mmol) is placed in the reaction bottle, adding methanol to 30 ml, adding hydroxylamine hydrochloride (2.8 g, 40.0 mmol), triethylamine (4.0 g, 40.0 mmol), room temperature 0.5 h, evaporate the solvent under reduced pressure, the residue dissolved in water and ethyl acetate, then ethyl acetate extraction the aqueous phase two, combined with the organic phase, the organic phase with saturated sodium chloride washing twice, dried with anhydrous sodium sulfate, filtered, reducing pressure and ethyl acetate to get trifluoromethyl benzamide oxime (u).The trifluoromethyl benzamide oxime: white solid; 3.92 g, yield 96.0%; |
93% | With hydroxyamino hydrochloride; potassium-t-butoxide In methanol; toluene | 4-Trifluoromethylphenyl-amidoxime Reaction Scheme 3, Step 1 4-Trifluoromethylphenyl-amidoxime A solution of 4-trifluoromethyl benzonitrile (Avocado 14514, 15 g) in toluene (200 ml) was treated with methanol (15 ml) followed by hydroxylamine hydrochloride (2.25 g) and potassium tert-butoxide (3.52 g). The mixture was heated to 80° C. and treated with further portions of hydroxylamine hydrochloride (1.07 g) and potassium tert-butoxide (3.52 g) after 2, 4 and 6 h. The mixture was stirred for 16 h, and then cooled. The solvents were evaporated and the residue partitioned between water (100 ml) and dichloromethane (200 ml). The aqueous layer was extracted with two further portions of dichloromethane (2*200 ml). The organic solutions were combined, dried (anhydrous magnesium sulphate), filtered and evaporated to give the title compound as a white solid (16.7 g, 93%). Mass spectrum, 215 [M+H]+. |
91% | With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In methanol | 2.4.A Step A: To a stirred suspension of 4-(trifluoromethyl)benzonitrile (1) (15 g, 87.7 mmol, 1 eq.) and; sodium hydrogencarbonate (8.8 g, 105.2 mmol, 1.2 eq.) in methanol (150 ml), hydroxylamine hydrochloride (7.3 g, 105.2 mmol, 1.2 eq.) was added portion wise and stirred overnight. After completion of the reaction (TLC data), the mixture was filtrated and the filtrate was carefully evaporated in vacuo at 35°C. The resulting residue was suspended in water (200 mL), stirred for 15 min and then filtrated to afford N'-hydroxy-4-(trifluoromethyl)benzimidamide (2) (16.2 g, 91 % yield) as white solid. |
91% | With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In methanol | 2.4.A Step A: To a stirred suspension of 4-(trifluoromethyl)benzonitrile (1) (15 g, 87.7 mmol, 1 eq.) and; sodium hydrogencarbonate (8.8 g, 105.2 mmol, 1.2 eq.) in methanol (150 ml), hydroxylamine hydrochloride (7.3 g, 105.2 mmol, 1.2 eq.) was added portion wise and stirred overnight. After completion of the reaction (TLC data), the mixture was filtrated and the filtrate was carefully evaporated in vacuo at 35°C. The resulting residue was suspended in water (200 mL), stirred for 15 min and then filtrated to afford N'-hydroxy-4-(trifluoromethyl)benzimidamide (2) (16.2 g, 91 % yield) as white solid. |
89% | With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In ethanol for 6h; Reflux; | Preparation and characterization of amidoximes 2a-g General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL). |
86% | With hydroxyamino hydrochloride; potassium carbonate In ethanol Reflux; | |
84% | With hydroxylamine In ethanol; lithium hydroxide monohydrate at 100℃; for 4h; Inert atmosphere; | |
79% | With hydroxylamine In ethanol; lithium hydroxide monohydrate for 3h; Reflux; Inert atmosphere; | |
70.2% | With hydroxyamino hydrochloride; sodium hydroxide In ethanol; lithium hydroxide monohydrate Reflux; | |
55% | With hydroxyamino hydrochloride; anhydrous sodium carbonate In methanol; lithium hydroxide monohydrate at 120℃; for 12h; Schlenk technique; Inert atmosphere; | |
42% | With hydroxyamino hydrochloride; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate Reflux; | |
With hydroxylamine In ethanol Heating; | ||
With hydroxyamino hydrochloride; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate at 80℃; for 3h; | (a) To a 500 ml three-necked flask were added 0.1 mol arylbenzonitrile, 0.368 mol hydroxyamine hydrochloride, 0.19 mol Na2CO3, and a mixture of ethanol and water (35 ml ethanol, 300 ml water). The mixture was refluxed at 80°C for 3 hours, cooled and stood to produce white crystal precipitate. The precipitate was dried to obtain aryl-N-hydroxylbenzamidine. | |
With hydroxyamino hydrochloride; N-ethyl-N,N-diisopropylamine In ethanol Reflux; | ||
With hydroxylamine | ||
With hydroxyamino hydrochloride In ethanol for 8h; Reflux; | ||
With hydroxylamine In ethanol; lithium hydroxide monohydrate for 1.5h; Reflux; Inert atmosphere; | [Method c] General procedure for one-pot synthesis of N-monosubstituted urea (4)from nitrile (1) (Scheme 3) General procedure: To the solution of nitrile (1) in EtOH (0.1 M) was added 50wt% aqueous hydroxylaminesolution (1.2 equiv). The mixture was stirred at reflux temperature for 1.5 h under nitrogen. After cooling to room temperature, the reaction mixture was concentratedunder reduced pressure. The crude amidoxime (2) product was dissolved in CH2Cl2(0.1 M), and then ArSO2Cl (TsCl or o-NsCl, 1.05 equiv) and DIPEA (1.05 equiv)were added at 0 oC. The mixture was stirred under nitrogen atmosphere at room temperature for 3 h or at reflux temperature for 1 h (see reference 3 for details).3 Themixture was concentrated under reduced pressure. The crude cyanamide (3) productwas dissolved in the mixture of 1 N aqueous HCl solution and EtOH (1 N HCl / EtOH= 1 : 4, v/v, reaction concentration = 0.1 M). The mixture was stirred at reflux temperaturefor 3 h under nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography. | |
With hydroxyamino hydrochloride; triethylamine In <i>tert</i>-butyl alcohol at 80℃; for 12h; | ||
With hydroxyamino hydrochloride; sodium hydroxide In ethanol; lithium hydroxide monohydrate for 4h; Reflux; | General procedure for the synthesis of N'-hydroxy-4-substituted benzimidamide (2). General procedure: To the solution of NaOH (5.93 g, 0.15 mol) in water (20 mL) and ethanol (120 mL), hydroxylamine hydrochloride (10.33 g, 0.15 mol) was added in one portion at room temperature. The resulting mixture was then stirred for 10 min, followed by the addition of 4-substituted cyanobenzene (1, 0.12 mol) and then heated to reflux for 4 h. After cooled to room temperature, the reaction mixture was evaporated in vacuo to remove ethanol. The obtained slurry was dissolved in ethyl acetate and filtered. The filtrate was collected, dried over anhydrous Na2SO4, and then concentrated to give corresponding compound 2, which was used in next step without any purification. | |
With hydroxylamine In ethanol; lithium hydroxide monohydrate for 3h; Reflux; Inert atmosphere; | ||
With hydroxyamino hydrochloride; anhydrous sodium carbonate In ethanol Reflux; | 5-(tert-butyl)-3-phenyl-1,2,4-oxadiazole (1a) General procedure: A round-bottom flask equipped with a magnetic stir bar and a reflux condenser was charged withbenzonitrile (1.03 g, 10.0 mmol), sodium carbonate (2.0 equiv.), hydroxylamine hydrochloride (2.0equiv.), and EtOH (15 mL). The mixture was heated to reflux overnight. After cooling to roomtemperature, the solvent was removed under reduced pressure. The resulting solid was suspendedin EtOAc and filtered over a pad of Celite. The filtrate was evaporated to dryness to give crudebenzamidoxime. Pivalic anhydride (1.1 equiv.) was added and the mixture was heated at 130 °C for 1 h. Aftercooling to room temperature, the mixture was diluted with EtOAc and the resulting solution waswashed with saturated NaHCO3 and brine. The organic layer was dried over Na2SO4 and thesolvent was evaporated. The residue was subjected to column chromatography (eluent:hexane/EtOAc = 40/1) and subsequent Kugelrohr distillation gave 1a as colorless oil (1.31 g, 65%). | |
With hydroxyamino hydrochloride; anhydrous sodium carbonate | ||
With hydroxyamino hydrochloride; anhydrous sodium carbonate In ethanol Sonication; | ||
With hydroxyamino hydrochloride; potassium carbonate In methanol for 2h; Inert atmosphere; Reflux; | ||
With hydroxyamino hydrochloride; anhydrous sodium carbonate In ethanol at 80℃; | ||
With hydroxylamine In ethanol; lithium hydroxide monohydrate for 3h; Reflux; | ||
With hydroxyamino hydrochloride; sodium hydroxide In ethanol for 2h; Reflux; | ||
With hydroxyamino hydrochloride; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate at 20℃; | ||
With hydroxylamine In acetonitrile for 3h; Reflux; | ||
With hydroxyamino hydrochloride; N-ethyl-N,N-diisopropylamine In ethanol for 4h; Reflux; | ||
With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In methanol for 6h; Reflux; | General procedure: The synthesis of oxadiazoles was taken by the reaction of the corresponding benzonitrile(8 mmol) and sodium bicarbonate (12.8 mmol) with hydroxylamine hydrochloride(12 mmol) in 15 mL of methanol. The reaction remained stirring for 6 h in reflux. Aftercooling, the solvent was removed under reduced pressure and the mixture was purifiedby extraction with ethyl acetate and water, and then with brine solution, affordingthe amidoxime. | |
With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In ethanol; lithium hydroxide monohydrate at 20℃; | ||
With hydroxylamine In ethanol for 4h; Reflux; | ||
With hydroxyamino hydrochloride; N-ethyl-N,N-diisopropylamine In ethanol Reflux; | ||
With hydroxyamino hydrochloride; potassium hydroxide In methanol at 20℃; Alkaline conditions; | ||
With hydroxyamino hydrochloride; potassium carbonate In methanol for 8h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 24 5-(3-Bromo-furan-2-yl)-3-(4-trifluoromethyl-phenyl)-[1,2,4]-oxadiazole The title compound was prepared similar to Example 20. From 3-bromo-furan-2-carboxylic acid (38 mg, 0.2 mmol) and 4-trifluoro-methylbenzamidoxime (41 mg, 0.2 mmol) was obtained 11 mg (15%) of the title compound. 1H NMR (CDCl3): 8.33 (d, J=8.7 Hz, 1H), 7.79 (d, J=8.7 Hz, 1H), 7.68 (d, J=2.1 Hz, 1H), 6.76 (d, J=2.1 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In ethanol; lithium hydroxide monohydrate at 100℃; for 3h; | N-Hydroxy-4-trifluoromethylbenzimidamide (47c). N-Hydroxy-4-trifluoromethylbenzimidamide (47c). 4-Trifluoromethylbenzonitrile 46c (1.37 g, 8.0 mmol) in ethanol (30 mL) was added to hydroxylamine hydrochloride (3.34 g, 48 mmol) and sodium hydrogen carbonate (2.54 g, 24 mmol) in water (30 mL) and the mixture was stirred at 100°C for 3 h. The ethanol was evaporated from the cooled mixture and the residue was poured into ice-cold water. The precipitate was collected by filtration, washed (water) and dried to give N-hydroxy-4-trifluoromethyl- benzimidamide 47c (1.60 g, 98%) as a white powder: 1 18-120°C (lit.95 128-129°C); 1H NMR ((CD3)2SO) δ 6.01 (2 H, br, NH2), 7.79 (2 H, d, J = 8.4 Hz, Ph 2,6-H2), 7.94 (2 H, d, J = 8.4 Hz, Ph 3,5-H2), 9.96 (1 H, s, OH); 13C NMR ((CD3)2SO) δ 124.98 (q, J = 3.1 Hz, 3,5-C2), 125.54 (q, J = 331 Hz, CF3), 126.05 (2,6-C2), 129.17 (1 -C), 137.28 (q, J = 28 Hz, 4-C), 149.76 (C=N); 19F NMR (CDCI3) δ -62.84 (CF3); MS m/z 205.0610 (M + H)+ (C8H8N2OF3 requires 205.0589). |
93% | With hydroxylamine In ethanol; lithium hydroxide monohydrate at 20℃; Reflux; | |
92% | With hydroxyamino hydrochloride; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate for 6h; Reflux; |
With hydroxyamino hydrochloride; anhydrous sodium carbonate In ethanol; lithium hydroxide monohydrate at 80℃; for 3h; Reflux; | a Intermediate 1: 2-(4-trifluoromethylphenyl)-4-methylpyrimidine 3-oxide The title compound was prepared according to scheme A with 4-trifluoromethylbenzonitrile as starting material, and a white solid was obtained.; Scheme A; General process for preparing of 2-aryl-4-methylpyrimidine 3-oxide from substituted arylbenzonitrile; (a) To a 500 ml three-necked flask were added 0.1 mol arylbenzonitrile, 0.368 mol hydroxyamine hydrochloride, 0.19 mol Na2CO3, and a mixture of ethanol and water (35 ml ethanol, 300 ml water). The mixture was refluxed at 80° C. for 3 hours, cooled and stood to produce white crystal precipitate. The precipitate was dried to obtain aryl-N-hydroxylbenzamidine. | |
12.6 g | With hydroxylamine In ethanol; lithium hydroxide monohydrate at 80℃; | 2- [4- (trifluoromethyl) phenyl] -1H- imidazole-4-carboxylic acid 1, 4-addition of 50% hydroxylamine aqueous solution (11.6g) in (trifluoromethyl) benzonitrile (10g) solution of ethanol (100), and stirred overnight at 80 ° C. After the reaction, the solvent was removed by distillation, and water was added. After collecting the insoluble matter was filtered dried to give the N- hydroxy-4- (trifluoromethyl) benzamidine (12.6g). MS (ESI) m / z: 205 (M + H) +. |
With hydroxyamino hydrochloride; sodium hydroxide In ethanol at 40℃; for 16h; | 68 A-145: A mixture of 4-(trifluoromethyl)benzonitrile (1 g, 5.84 mmol), hydroxylamine hydrochloride (1.22 g, 17.53 mmol) and NaOH (0.7 g, 17.53 mmol) in ethanol (20mL) as stirred at 40 °C for 16 hours. After cooling to room temperature, the reaction mixture was partially concentrated under reduce pressure to remove most of the EtOH and then diluted with FLO (20 mL). The mixture was extracted with EtOAc (30 mL x 2). The combined organic phase was washed with brine (15 mL), dried over NaiSCE, filtered and concentrated to give the crude product (1.46 g, 6.96 mmol) as a solid. LCMS Rt = 0.41 min in in 1.5 min chromatography, 5-95 AB, MS ESI calcd. for C8H8F3N2O [M+H]+ 205.1, found 205.0. | |
With hydroxyamino hydrochloride; Sodium hydrogenocarbonate In ethanol for 15h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate at 160℃; for 0.5h; Sealed tube; Inert atmosphere; Microwave irradiation; | 5 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method D; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (3 eq, 50% solution in EtOAc) and triethylamine (5 eq). The reaction vessel was sealed under argon atmosphere and the mixture was heated under microwave conditions at 160°C for 30min. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature. The organic layer was washed twice with 1N HCl, once with H2O and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired 1,2,4-oxadiazole derivative.; 4.1.3.5 5-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-3-[(4-trifluoromethyl)phenyl]-1,2,4-oxadiazole 36 1H NMR (DMSO-d6, 400 MHz): δ = 8.24 (d, J = 8.1 Hz, 2H), 8.08 (d, J = 16.1 Hz, 1H), 7.96 (d, J = 8.3 Hz, 2H), 7.53 (d, J = 4.0 Hz, 1H), 7.35 (d, J = 3.9 Hz, 1H), 7.11 (d, J = 16.1 Hz, 1H); 13C NMR (DMSO-d6, 101 MHz): δ = 175.95, 167.52, 141.28, 135.51, 133.62, 132.54, 132.01, 128.33, 126.78, 126.75, 126.71, 126.67, 125.66, 122.96, 116.85, 109.25; LC/MS (ESI): 401.14 [M-H]-; HRMS (TOF, ESI+) cald for C15H9N2OF3SBr (M + H)+ 400.9571, found 400.9570; yellow powder. Method C - Two-step conversion yield determined by LC/MS = 3%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate Reflux; Inert atmosphere; | 1 General procedure for two steps synthesis (Method C) and one-step synthesis (Method D) of 1,2,4-oxadiazole derivatives 33-36 General procedure: Method C; To a stirred solution of acrylic acid (200mg, 1 eq) and substituted amidoxime (1 eq) in dry ethyl acetate (5-10mL) were added dropwise T3P (2.5 eq, 50% solution in EtOAc) and triethylamine (3 eq-5 eq), and the mixture was refluxed under argon atmosphere for 24h. The completion of reaction was confirmed by TLC. The mixture was cooled to room temperature and poured into ice/water. The aqueous layer was extracted twice with EtOAc and then the organic layer was washed twice with saturated NaHCO3, and once with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel flash chromatography (cyclohexan/EtOAc) to afford the desired acylamidoxime.; The corresponding acylamidoxime (1 eq) was placed under argon atmosphere, anhydrous THF (3 mL) and TBAF (0.1 eq, 1 M in THF) was added. The mixture was stirred at room temperature for 16-18 h. The completion of reaction was confirmed by TLC. The solvent was evaporated and EtOAc was added. The organic layer was washed twice with water and twice with brine. The organic layer was dried under Na2SO4 and concentrated under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydroxide / dimethyl sulfoxide / 24 h / 20 °C / Sealed tube 2: bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)rhodium (III)]; (2,2,2-trifluoroacetyl)oxysilver / acetonitrile; lithium hydroxide monohydrate / 24 h / 120 °C / Schlenk technique; Sealed tube; Inert atmosphere |
Tags: 22179-86-8 synthesis path| 22179-86-8 SDS| 22179-86-8 COA| 22179-86-8 purity| 22179-86-8 application| 22179-86-8 NMR| 22179-86-8 COA| 22179-86-8 structure
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P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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