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CAS No. : | 56-57-5 | MDL No. : | MFCD00006738 |
Formula : | C9H6N2O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YHQDZJICGQWFHK-UHFFFAOYSA-N |
M.W : | 190.15 | Pubchem ID : | 5955 |
Synonyms : |
4-NQO;Nitrochin
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P201-P308+P313 | UN#: | 2811 |
Hazard Statements: | H350 | Packing Group: | Ⅲ |
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 |
---|---|---|
92% | With trifluorormethanesulfonic acid; potassium nitrate; trifluoroacetic acid at 0℃; for 25h; | |
88% | With sulfuric acid; nitric acid In water at 65℃; for 2h; | |
88% | With sulfuric acid; nitric acid at 65℃; | Compound 3 was prepared by a method described elsewhere [Taylor Jr, E. C. et al. 3-Methyl-4-nitroρyridine-l-oxide. Org. Synth. 1963. Coll. Vol. 4. 654-656]. In brief, compound 2 (19.10 g, 0.13 mol) was dissolved in concentrated sulfuric acid and warmed to 65 0C. Nitric acid (65%, 1.1 eq, 15 mL) was added slowly, dropwise. The reaction stirred at 65 0C for 2 hours. The reaction was cooled and poured on ice. The product precipitated as yellow solid, which was filtered off, washed with 5% Na2CO3 (1 x 10 mL) water (2 x 10 mL), ethanol (1 x 10 mL) and dried. Yield: 21.90 g (88%). 1H NMR (CDCl3) δ 7.85-7.94 (m, 2H, Ar), 8.21 (d, IH, J= 6.58 Hz5 Ar)5 8.53 (d, IH, J = 7.30 Hz5 Ar), 8.73-8.86 (m, IH5 Ar). 1H NMR was identical with 1H NMR spectrum in literature [Yokoyama, A. et al. Nitration of Quinoline 1-oxide: Mechanism of Regioselectivity. Chem. Pharm. Bull. 1997, 45, 279-283]. |
23% | With sulfuric acid; nitric acid at 70℃; for 3h; | |
With sulfuric acid; nitric acid | ||
With sulfuric acid; potassium nitrate | ||
With sulfuric acid; nitric acid | ||
With sulfuric acid; nitric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal; ethanol Hydrogenation; | ||
With sodium dithionite; ethanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogenchloride; triethylbutylammonium chloride In water; acetonitrile at 65℃; for 0.5h; | |
84% | With aluminium trichloride In acetonitrile at 20℃; for 24h; | |
80% | With N-benzyl-N,N,N-triethylammonium chloride; ethenetetracarbonitrile In 1,4-dioxane for 3h; Ambient temperature; |
With trichlorophosphate | ||
With ethyl acetate; phosphorus trichloride | ||
With hydrogenchloride | ||
With hydrogenchloride In acetonitrile | ||
With hydrogenchloride In water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide | ||
With hydrogen bromide Heating; | ||
Multi-step reaction with 2 steps 1: Na2S2O4; ethanol; H2O 2: aqueous sulfuric acid; sodium nitrite / Beh. einer aus obigen Verbindungen bereiteten Diazoniumsalz-Lsg. mit Kupfer(I)-bromid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With methanol; sodium acetate; nickel; acetic acid at 120℃; Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With phosphorous acid trimethyl ester In dichloromethane Irradiation; | |
With chloroform; phosphorus tribromide | ||
With phosphorus tribromide; ethyl acetate |
With phosphorous acid trimethyl ester In dichloromethane Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; palladium Hydrogenation; | ||
With water In aq. phosphate buffer Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With phosphorus(V) oxybromide In chloroform at 0℃; for 2h; | |
52% | Stage #1: 4-nitroquinoline-N-oxide With phosphorus(V) oxybromide In chloroform for 2h; Cooling with ice; Stage #2: With sodium hydroxide In chloroform; water Cooling with ice; | Compound 4 was prepared as described elsewhere [Hamana, M. et al. A new deoxidation reaction of aromatic tertiary amine oxides. Reaction of 4-nitroquinoline 1- oxide with phosphorus bromide. Chem. Abstr. 1957. 51. 6639]. In brief, compound 3 (1.86 g, 9.8 mmol) was dissolved in chloroform and cooled in an ice-bath. POBr3 (1.25 eq) was added and the reaction stirred in an ice-bath for 2 hours. The reaction was poured on ice, pH was adjusted to 9 with 2M NaOH and extracted with DCM (3 x 80 mL). The product was purified by column chromatography, eluent DCM. Yield: 1.30 g (52 %). 1H NMR (CDCl3) δ 7.63-7.94 (m, 2H, Ar)5 8.06 (s, IH5 Ar)5 8.17 (t5 IH5 J = 7.16, 6.84Hz, Ar)5 8.38 (d, IH, J= 8.76 Hz5 Ar). 1H NMR was identical with 1H NMR spectrum in literature [Wozniak, M. et al. Amination of 4-nitroquinoline with Liquid Methylamine/Potassium permanganate. Chem. Heterocyc. Comp. 1998, 34, 837-840]. |
50% | With phosphorus(V) oxybromide In chloroform at 0℃; for 2h; | 4-Nitroquinoline 1-oxide (940 mg, 4.9 mmol) in chloroform (12 mL) was cooled, to 0 °C. To this solution, POBr3 (1.77 g, 6.2 mmol) was added, in small portions. The mixture was stirred at 0 °C for 2 h and diluted with DCM (50 mL), and poured on ice (50 g). To this suspension, 1 M NaOH was added to adjust pH to about 9. Layers were separated and the organic layer was washed, with water (2 × 50 mL) and dried over MgSO4 and concentrated. The crude product was purified by silica chromatography to afford 2-bromo-4-nitroquinoline as a yellow solid (620 mg, 50%). |
With chloroform; phosphorus tribromide | ||
With phosphorus(V) oxybromide In chloroform at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; sulfur trioxide; potassium nitrate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetyl chloride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Perbenzoic acid In 1,4-dioxane; water at 20℃; Ea, ΔS%; | ||
With dihydrogen peroxide In water; acetic acid at 70℃; for 72h; | ||
With dihydrogen peroxide; acetic acid at 70℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ascorbic acid 2.) acetic acid; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.2% | With triethylamine In chloroform-d1; water for 12h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With perchloric acid; ethanol In dichloromethane for 48h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With iron; acetic acid; for 3h;Reflux; | 4-Nitroquinoline-N-oxide (100 mg, 0.53 mmol) and Fe (264 mg, 4.24 mmol) was dissolved in 2 mL acetic acid and refluxed for 3 h. The reaction mixture was cooled to room temperature and basified by using Na2C03 to pH? 7. The solution was filtered through celite bed and the filtrate was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to afford the desired quinolin-4-amine (A) (76 mg, 99 %). |
99% | With iron; acetic acid; for 3h;Reflux; | 4-Nitroquinoline-N-oxide (100 mg, 0.53 mmol) and Fe (264 mg, 4.24 mmol) was dissolved in 2 mL acetic acid and refluxed for 3 h. The reaction mixture was cooled to room temperature and basified by using Na2CO3 to pH ?7. The solution was filtered through celite bed and the filtrate was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to afford the desired quinolin-4-amine (A) (76 mg, 99%). |
79% | With sodium hydroxide; In acetic acid; | Step 1 A suspension of 4-nitroquinoline N-oxide (10 g, 52.5 mmol) and metal iron (26.4 g, 0.47 mol) in acetic acid (500 ml) was stirred under heating at 110 C. for 3 hr. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. To the residue was added an aqueous sodium hydroxide solution to make the solution alkaline, which was followed by extraction with chloroform (5 ml*6). The orgariic layer was washed with water and saturated brine, dried over sodium sulfate and concentrated under reduced pressure to give 4-aminoquinoline (6.0 g, 79%, brown crystals). |
79% | With iron; acetic acid; at 20 - 110℃; for 3h; | (525 mmol) of 4-nitroquinoline N-oxide was dissolved in 5000 mL of acetic acid, and 264 g (4.73 mil) of iron powder was charged with electric stirring at room temperature. The mixture was heated to 110 C for 3 hours, Thin layer tracking reaction process, developing agent: ethyl acetate: triethylamine = 3mL: 4d until the reaction is complete. With the reaction process, the slurry of ferrous acetate precipitates Out, stirring becomes very difficult. The filtrate was concentrated under reduced pressure. The residue was centrifuged at 1000 mL of 35% sodium hydroxide solution. After thorough stirring, the mixture was extracted with chloroform (500 mL X6). The organic layers were washed with 1000 mL of water and 1000 mL of brine, dried over anhydrous sodium sulfate and concentrated to give 4-aminoquinoline, Brown solid 60 g, yield 79 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | With <i>N</i>,<i>N</i>-dimethyl-aniline In acetonitrile for 2h; Ambient temperature; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With sodium azide In ethanol for 1h; Heating; | |
81% | With sodium azide In 1,4-dioxane; ethanol; water at 20℃; for 48 - 72h; Darkness; | |
80.6% | With sodium azide In 1,4-dioxane; ethanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydrogenchloride In water at 100℃; for 0.166667h; | |
93% | With hydrogenchloride In chloroform for 30h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrogen bromide In water at 100℃; | |
68% | With hydrogen bromide In chloroform Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine In chloroform for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With O-Methylhydroxylamin; potassium <i>tert</i>-butylate; zinc(II) chloride In N,N-dimethyl-formamide Ambient temperature; | |
21% | 22 Example 22 Example 22 43 mg of 3-amino-4-nitroquinoline N-oxide was obtained according to the same manner as that described in Example 19 except for using 4-nitroquinoline N-oxide (190 mg, 1 mmol) in place of 4-nitropyridine N-oxide (yield: 21%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | Stage #1: 4-nitroquinoline-N-oxide; phenyllithium In tetrahydrofuran; diethyl ether; cyclohexane at -30℃; for 1h; Stage #2: With 9-fluorenone In tetrahydrofuran; diethyl ether; cyclohexane at -30 - 25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | Stage #1: 2-thienyl lithium; 4-nitroquinoline-N-oxide In tetrahydrofuran at -30℃; for 1h; Stage #2: With 9-fluorenone In tetrahydrofuran at -30 - 25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
5% | Stage #1: n-butyllithium; 4-nitroquinoline-N-oxide In tetrahydrofuran; hexane at -30℃; for 1h; Stage #2: With 9-fluorenone In tetrahydrofuran; hexane at -30 - 25℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With lead(IV) acetate In methanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethyl phosphite / CH2Cl2 / Irradiation 2: 34 percent / Sn; aq. HCl / ethanol / 2 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 80.6 percent / aq. sodium azide / dioxane; ethanol / 20 °C 2: 79.3 percent / CHCl3 / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 79 percent / Fe; AcOH / 3 h / 110 °C 2: 82 percent / Br2; AcOH / 0.5 h / 20 °C 3: 47 percent / HNO3; H2SO4 / 1 h / 0 °C | ||
Multi-step reaction with 3 steps 1: iron; acetic acid / 3 h / 20 - 110 °C 2: bromine; acetic acid / 0.5 h / 0 - 20 °C 3: nitric acid; sulfuric acid / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 79 percent / Fe; AcOH / 3 h / 110 °C 2: 82 percent / Br2; AcOH / 0.5 h / 20 °C 3: 47 percent / HNO3; H2SO4 / 1 h / 0 °C 4: 94 percent / H2; HBr; AcOH / 10percent Pd/C / ethanol / 6 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 79 percent / Fe; AcOH / 3 h / 110 °C 2: 82 percent / Br2; AcOH / 0.5 h / 20 °C 3: 47 percent / HNO3; H2SO4 / 1 h / 0 °C 4: 94 percent / H2; HBr; AcOH / 10percent Pd/C / ethanol / 6 h / 20 °C 5: pyridine / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 23 percent / PBr3 / 0.5 h / Ambient temperature 2: 16 percent / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 23 percent / PBr3 / 0.5 h / Ambient temperature 2: 70 percent / ethanol / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Br2 / CHCl3 / 1 h 2: air |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: hydrobromic acid / Heating 2: phosphorus trichloride 3: Heating 4: aq. base 5: SOCl2 / CHCl3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: hydrobromic acid / Heating 2: phosphorus trichloride 3: Heating 4: aq. base 5: SOCl2 / CHCl3 6: trimethylamine / CHCl3 7: 56 percent / O2 / 4 h / Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: hydrobromic acid / Heating 2: phosphorus trichloride 3: Heating 4: aq. base 5: SOCl2 / CHCl3 6: trimethylamine / CHCl3 7: 67 percent / O2 / 4 h / Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: hydrobromic acid / Heating 2: phosphorus trichloride 3: Heating 4: aq. base 5: SOCl2 / CHCl3 6: trimethylamine / CHCl3 7: 45 percent / O2 / 7 h / Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 86 percent / trimethyl phosphite / CH2Cl2 / Irradiation 2: 44 percent / potassium nitrate, 98.5percent H2SO4 / 65 - 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 86 percent / trimethyl phosphite / CH2Cl2 / Irradiation 2: 16 percent / potassium nitrate, 98.5percent H2SO4 / 65 - 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 86 percent / trimethyl phosphite / CH2Cl2 / Irradiation 2: 44 percent / potassium nitrate, 98.5percent H2SO4 / 65 - 75 °C 3: 100 percent / H2 / 10percent Pd/C / acetic acid / 1 h / 2585.7 Torr / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 86 percent / trimethyl phosphite / CH2Cl2 / Irradiation 2: 44 percent / potassium nitrate, 98.5percent H2SO4 / 65 - 75 °C 3: 100 percent / H2 / 10percent Pd/C / acetic acid / 1 h / 2585.7 Torr / Ambient temperature 4: 89 percent / 1 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 98 percent / NaN3 / aq. ethanol / 1 h / Heating 2: 92 percent / CHCl3 3: 63 percent / dioxane; H2O 4: 92 percent / 15percent H2O2, 6N NaOH / acetone / 2 h / 50 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 98 percent / NaN3 / aq. ethanol / 1 h / Heating 2: 92 percent / CHCl3 3: 63 percent / dioxane; H2O |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 98 percent / NaN3 / aq. ethanol / 1 h / Heating 2: 92 percent / CHCl3 3: 63 percent / dioxane; H2O 4: 57 percent / 30percent H2O2 / acetic acid / 5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 98 percent / NaN3 / aq. ethanol / 1 h / Heating 2: 92 percent / CHCl3 3: 63 percent / dioxane; H2O 4: 92 percent / 15percent H2O2, 6N NaOH / acetone / 2 h / 50 - 60 °C 5: 23 percent / 30percent H2O2 / acetic acid / 4 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 98 percent / NaN3 / aq. ethanol / 1 h / Heating 2: 92 percent / CHCl3 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: phosphoryl chloride 2: 135 - 145 °C | ||
Multi-step reaction with 2 steps 1: acetyl chloride 2: 135 - 145 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: phosphoryl chloride 2: ethanol | ||
Multi-step reaction with 2 steps 1: acetyl chloride 2: ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; water | 117 4-Hydroxy-3-quinolinecarbonitrile Example 117 4-Hydroxy-3-quinolinecarbonitrile A mixture of 15.3 g of 4-nitroquinoline N-oxide, 260 ml of N , N -dimethylformamide and 10.5 g of potassium cyanide is heated in an oil bath for 5 hours at 80-90oC. The reaction is concentrated in vacuo , treated with water and chloroform, filtered through diatomaceous earth, and the layers separated. The water layer is cooled, made weakly acidic (pH 4-5), and allowed to stand overnight. The product is collected to give 5.85 g of tan crystals, mp 268-271oC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In not given mixing equimolar amounts of metal porphyrin and ligand in acetone or itsmixture with hexane; washing of ppt. with acetone, drying in air, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With boron trifluoride diethyl etherate In chloroform | |
With boron trifluoride diethyl etherate In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; N,N-dimethyl-formamide Heating; | 57 To stirred mixture of 3-benzyloxyphenol (2.00 g, 10 mmole), potassium carbonate (4.15 g, 30 mmole) and 25 ml DMF was added 4-nitroquinoline-N-oxide (2.09 g, 1 1 mmole). This was stirred and heated to a gentle reflux and kept there overnight. The reaction mixture was cooled to room temperature and quenched into 250 ml water. The solid that formed was collected by filtration, washed with water, and dried to give a beige solid, 2.79 g. A mixture of this N-oxide (250 mg, 0.73 mmole), p-tosyl chloride (167 mg, 0.87 mmole, 1.2 eq) and dichloroethane, 10 ml, was stirred and heated to reflux. This mixture was stirred for 1 hour, cooled, 10% sodium carbonate solution was added and stirred overnight. The reaction mixture was filtered, the solid was washed with water, and dried to give the product, (if no solid is present the mixture is portioned between water and ether, the ether layer was dried over sodium sulfate, filtered, evaporated, and the residue chromatographed on silica gel using a chloroform to 15% methanol in chloroform gradient, fractions containing product are combined, evaporated to give product) 149 mg (60%), mp 262-5 0C; HRMS: calcd for C22H17NO3 + H+, 344.12812; found (ESI-FTMS, [M+H]1+), 344.12832. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 4-nitroquinoline-N-oxide; N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine With trifluoroacetic acid In dichloromethane at 20℃; for 23h; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In dichloromethane Saturated solution; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With chloroformic acid ethyl ester In 1,2-dichloro-ethane at 40 - 65℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | Stage #1: 4-nitroquinoline-N-oxide; phenylmagnesium bromide In tetrahydrofuran at -60℃; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at -60 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: iron; acetic acid / 3 h / Reflux 2: triethylamine / dichloromethane / 1 h / 23 °C 3: triethylamine / dimethyl sulfoxide / 12 h / 23 °C | ||
Multi-step reaction with 3 steps 1: iron; acetic acid / 3 h / Reflux 2: triethylamine / dichloromethane / 1 h / 20 °C 3: triethylamine / dimethyl sulfoxide / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: iron; acetic acid / 3 h / Reflux 2: triethylamine / dichloromethane / 1 h / 23 °C | ||
Multi-step reaction with 2 steps 1: iron; acetic acid / 3 h / Reflux 2: triethylamine / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 23h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium methylate / methanol / 48 h / 60 °C / Inert atmosphere 2: N,N-Dimethyltrimethylsilylamine; tetramethylammonium fluoride / N,N-dimethyl-formamide / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With sodium methylate In methanol at 60℃; for 48h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: phosphorus trichloride / chloroform / 1 h / 0 °C / Reflux 2: ethanol / 3 h / -10 - 155 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: phosphorus trichloride / chloroform / 1 h / 0 °C / Reflux 2.1: ethanol / 3 h / -10 - 155 °C 3.1: n-butyllithium / diethyl ether; hexane / 2 h / -78 °C 3.2: 0.33 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 66% 2: 31% | With phosphorus trichloride In chloroform at 0℃; for 1h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: phosphorus trichloride / chloroform / 1 h / 0 °C / Reflux 2: ethanol / 3 h / -10 - 155 °C 3: sulfuric acid; N-Bromosuccinimide / 48 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(l) iodide In toluene at 50℃; for 9h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | In 5,5-dimethyl-1,3-cyclohexadiene at 100℃; for 20h; Sealed tube; Green chemistry; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dihydrogen peroxide; acetic acid 2: nitric acid; sulfuric acid | ||
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15 h / 0 - 20 °C 2: sulfuric acid; nitric acid / 3 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate; silver(I) triflimide at 120℃; for 12h; Sealed tube; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | In neat (no solvent) at 130℃; for 1h; Sealed tube; Inert atmosphere; regioselective reaction; | |
42% | With [bis(acetoxy)iodo]benzene In 1,2-dichloro-ethane at 80℃; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With p-toluenesulfonylanhydride; tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; for 4h; Schlenk technique; regioselective reaction; | 4.3 General procedure for C-H trifluoromethylthiolation of heteroaryl N-oxides General procedure: A mixture of heteroaryl N-oxide (0.4mmol), AgSCF3 (166.3mg, 0.8mmol), Ts2O (195.8mg, 0.6mmol), and n-Bu4NI (295.5mg, 0.8mmol) was added in a 25mL Schlenk tube, and then THF (4.0mL) was added. The mixture was stirred at room temperature for 4h. After the reaction was complete, saturated NH4Cl solution was added. The resulting mixture was extracted with EtOAc for three times. The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (PE/EA=100:1) to give the desired product (2a-2w).f |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With fac-tris(2-phenylpyridinato-N,C2')iridium(III); potassium carbonate In acetonitrile at 20℃; for 84h; Sealed tube; Inert atmosphere; Irradiation; | C2 Trifluoromethylation of Quinoline N-Oxides; General Procedure General procedure: To a 10 mL vial were added in sequence a magnetic stir bar, substrate1 (0.10 mmol), Togni’s reagent (0.12 mmol, 1.2 equiv), K 2 CO 3 (0.12mmol), fac-Ir III (ppy) 3 (0.01 mmol, 10 mol%), and anhyd MeCN (1.0 mL)and the vial was sealed. The mixture was evacuated by four freeze-pump-thaw cycles and back-filled with N 2 . Then, the vial containingthe reaction mixture was irradiated by 5 W blue LEDs at rt for 3.5days. After reaction completion, the contents of the vial was evaporat-ed under reduced pressure and the residue was purified by precipita-tion thin-layer chromatography (PTLC) using PE/EtOAc (40:1 to 1:1depending on the substrates) as the eluent to afford the desired product 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; Trimethylacetic acid at 80℃; for 20h; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With methanesulfonic acid at 60℃; for 3h; |
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
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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