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CAS No. : | 16498-20-7 | MDL No. : | MFCD00088689 |
Formula : | C8H7NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MQSGCURTKWHBRX-UHFFFAOYSA-N |
M.W : | 181.15 | Pubchem ID : | 85460 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.13 |
TPSA : | 64.28 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.47 cm/s |
Log Po/w (iLOGP) : | 1.73 |
Log Po/w (XLOGP3) : | 1.32 |
Log Po/w (WLOGP) : | 1.37 |
Log Po/w (MLOGP) : | 0.8 |
Log Po/w (SILICOS-IT) : | -0.06 |
Consensus Log Po/w : | 1.03 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.07 |
Solubility : | 1.54 mg/ml ; 0.00851 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.27 |
Solubility : | 0.971 mg/ml ; 0.00536 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.81 |
Solubility : | 2.81 mg/ml ; 0.0155 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.46 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-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 |
---|---|---|
76.3% | With palladium on activated charcoal; hydrogen In tetrahydrofuran at 40 - 45℃; for 10 h; Autoclave | (3) 2L autoclave was charged with 102.0g (0.54mol) of Intermediate 2,3.7g palladium on carbon catalyst, 700 g of the of THF, warmed to 40 ~ 45 , maintaining the internal pressure of hydrogen charging 5 ~ 7atm 10h reaction, the reaction completion, said palladium-carbon catalyst was filtered off, the filtrate removal of THF, to give 62.2 g of red-brown oily liquid, namely intermediate 3, yield: 76.3percent |
190 mg | With palladium on activated charcoal; hydrogen In methanol at 20℃; | Compound 27 (200mg), methanol (2OmL), and Pd/C (100mg) catalysts were put into a 5OmL of one-necked flask, and fully stirred to dissolve. And then hydrogen gas was bubbled into the reaction mixture at room temperature and reacted overnight. After, the reaction mixture wasfiltered and the filtrate was concentrated in vacuum to afford 190mg Compound 28, which was used in the next step without further purification. MS: 152 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With tert.-butylnitrite; In acetonitrile; at 20℃; for 1h; | 1 mmol of 1,4-benzodioxane was added to the reaction flask, dissolved in 2 mL of acetonitrile, and 145 uL of t-butyl nitrite was added. The mixture was stirred at room temperature for 1 hour. After the reaction was completed, the organic solvent was removed by a rotary evaporator. Solvent, column chromatography gave the product nitro product, the reaction yield was 80% |
76.7% | With nitric acid; In water; at 20 - 80℃; for 6h; | (2) To a 2L three flask 100g (0.74mol) benzo-dioxane, a 108.5g (1.17mol) of concentrated nitric acid (68% AR) and 75.9g of water were mixed to prepare a solution , room temperature 20 , under mechanical stirring, the solution was added dropwise equipped benzodioxan-necked flask, dropping violent exothermic, the temperature rose to 65 , precipitated brown solid finish in 1h drip, drip Bi 55 ~ 65 incubation reaction 1h, then heated to 75 ~ 80 heat stirring reaction 5h, the reaction was completed, added with vigorous stirring 400g of water was stirred, filtered, 500g cake was rinsed with water until the filtrate to pH 7, drying pale yellow 102.0 g of solid, that is, intermediate 2, yield 76.7%, |
210 mg | With nitric acid; at 0℃; for 0.166667h; | Concentrated nitric acid (2.5mL) was put into a 5OmL of three-necked flask, and cooled to 0C. Then, Compound 1 (200mg) was added in portions during a period of 5 mins, and stirred for another 5 minutes. After, the reaction mixture was poured into ice water, filtered, and the filter cake was dried in vacuum to afford 210mg Compound 27, light yellow solid. MS: 182(M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; nitric acid; acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid at 140℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With maghemite-palladium nanocomposite; hydrogen In ethanol; ethyl acetate at 30℃; for 0.0125h; | |
91% | With water at 20℃; Inert atmosphere; chemoselective reaction; | |
87% | With hydrogen In ethanol; water at 40℃; for 2h; | 2.7. Catalytic test General procedure: To evaluate the catalytic performance of Pd/ Cu-BDC MOF- Perlite, nitoarene (1 mmol) and Pd/ Cu-BDC MOF-Perlite (0.02 g) were charged in a reaction vessel containing H 2 O: EtOH (1:1) mix- ture (8 mL). Then, the reaction mixture was stirred at 40 °C and hydrogen gas with pressure of 1 bar was purged. The reaction was monitored via TLC and upon completion of the reaction, the mix- ture was cooled and Pd/ Cu-BDC MOF-Perlite was separated. The product was achieved after evaporation of the solvent and the re- covered catalyst was washed several times with EtOH and dried in oven at 80 °C overnight. The yields of the hydrogenation reactions have been estimated via GC analysis. |
84% | With phenylsilane; C78H88Cl2N4Ni In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; chemoselective reaction; | |
76.3% | With palladium on activated charcoal; hydrogen In tetrahydrofuran at 40 - 45℃; for 10h; Autoclave; | 1.3 (3) 2L autoclave was charged with 102.0g (0.54mol) of Intermediate 2,3.7g palladium on carbon catalyst, 700 g of the of THF, warmed to 40 ~ 45 , maintaining the internal pressure of hydrogen charging 5 ~ 7atm 10h reaction, the reaction completion, said palladium-carbon catalyst was filtered off, the filtrate removal of THF, to give 62.2 g of red-brown oily liquid, namely intermediate 3, yield: 76.3% |
32% | With nickel; hydrazine In ethanol Heating; | |
With hydrogenchloride; acetone Electrolysis; | ||
With ethanol; palladium Hydrogenation; | ||
With hydrogenchloride; iron | ||
94 %Chromat. | With formic acid; triethylamine In tetrahydrofuran at 100℃; for 15h; Inert atmosphere; Sealed tube; chemoselective reaction; | |
190 mg | With palladium on activated charcoal; hydrogen In methanol at 20℃; | 35.3 Step 3: Synthesis of 2,3 -dihydrobenzo[b] [1 ,4]dioxin-6-amine (Compound 28) Compound 27 (200mg), methanol (2OmL), and Pd/C (100mg) catalysts were put into a 5OmL of one-necked flask, and fully stirred to dissolve. And then hydrogen gas was bubbled into the reaction mixture at room temperature and reacted overnight. After, the reaction mixture wasfiltered and the filtrate was concentrated in vacuum to afford 190mg Compound 28, which was used in the next step without further purification. MS: 152 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 3% 2: 7.2% 3: 83% | With nitric acid; acetic acid at 25℃; for 0.5h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitric acid; acetic acid 1.) 25 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); sodium iodide 1.) carbon tetrachloride, 12 h, reflux, 2.) acetone, 2 h, reflux; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With 5-methyl-1,3 dinitropyrazole; ytterbium(III) tris(trifluoromethanesulfonate) In acetonitrile at 80℃; for 16h; Inert atmosphere; | 3 Example 1: Preparation of compound I-1 General procedure: Under an argon atmosphere, naphthalpines (25.6 mg, 0.2 mmol), ytterbium trifluoromethanesulfonate (12.4 mg, 0.02 mmol), 5-methyl-1,3 dinitropyrazole (51.6 mg, 0.3 mmol) and dried acetonitrile (1.0 mL) were added to the reaction tube dried and equipped with a magnetic stirrer, and the resulting mixture was reacted at 80 °C for 16 hours. After the reaction ended, it was cooled to room temperature, the mixture was filtered with diatomaceous earth, washed with ethyl acetate, the solvent was removed by distillation under reduced pressure, and the column chromatography was separated and purified to obtain Compound I-1 (white solid, 94% yield). |
aus Verb. (I), HNO3; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With sodium hexamethyldisilazane In tetrahydrofuran at 150℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 78% 2: 9% 3: 3% 4: 9% | With nitric acid In acetic anhydride at -40℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 72% 2: 18% | With nitro acetate In acetic anhydride at -30 - -10℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 43.5% 2: 25.5% 3: 18.5% 4: 3% | With sulfuric acid; nitric acid at -50℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 21% 2: 31% 3: 38% | With nitro acetate In acetic anhydride at -30 - -10℃; for 2h; | |
1: 38% 2: 31% 3: 21% | With sulfuric acid; nitric acid In acetic anhydride at -50 - -10℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: sodium tetrahydridoborate / ethanol 2: 76 percent / N,N-dimethylaniline / diethyl ether / 2 h / Heating 3: 18 percent / acetyl nitrate / acetic anhydride / 2 h / -30 - -10 °C | ||
Multi-step reaction with 2 steps 1: sodium tetrahydridoborate / ethanol 2: 21 percent / nitric acid; H2SO4 / acetic anhydride / 2 h / -50 - -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 76 percent / N,N-dimethylaniline / diethyl ether / 2 h / Heating 2: 18 percent / acetyl nitrate / acetic anhydride / 2 h / -30 - -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide; water / 100 °C 2: glacial acetic acid; nitric acid | ||
Multi-step reaction with 2 steps 1: sodium carbonate / glycerol / Heating 2: nitric acid / 60 °C | ||
Multi-step reaction with 2 steps 1: sodium hydroxide / N,N-dimethyl-formamide / 90 °C 2: nitric acid / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aqueous hydrochloric acid; iron-powder 2: phosphorus (III)-chloride; toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium; ethanol / Hydrogenation 2: acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium; ethanol / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: nitric acid 2: sulfuric acid; nitric acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: nickel; hydrazine / ethanol / Heating 2: acetic acid / 1.5 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: nickel; hydrazine / ethanol / Heating 2: acetic acid / 1.5 h / Reflux 3: hydrogenchloride; tin(II) chloride dihdyrate / ethanol; water / 1.5 h / 50 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: nickel; hydrazine / ethanol / Heating 2: acetic acid / 1.5 h / Reflux 3: hydrogenchloride; tin(II) chloride dihdyrate / ethanol; water / 1.5 h / 50 °C / Reflux 4: acetic acid / 1.5 h / 80 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With bismuth (III) nitrate pentahydrate In benzene at 70 - 80℃; for 2h; Inert atmosphere; | General procedure for ipso-nitration of aryl and heteroaryl boronic acids: General procedure: The mixture of aryl boronic acid (50 mg, 1 equiv) and bismuth (III) nitrate (2 equiv) in toluene or benzene (2 mL) was refluxed for 1.5-2 h. Reaction mixture was allowed to cool to room temperature and was filtered through Whatman filter paper. Residue was washed with ethyl acetate followed by DCM. Combined organic layers were evaporated on a rotary evaporator. Crude product was purified by silica gel column chromatography (⋕100-200) using EtOAc/hexane (1:99 to 5:95) as mobile phase. |
85% | With N-Bromosuccinimide; [bis(trifluoroacetoxy)iodo]benzene; sodium nitrite In acetonitrile at 20℃; for 3h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / methanol / 20 °C 2: ethanol / 75 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / methanol / 20 °C 2: ethanol / 75 °C / Inert atmosphere 3: sodium azide / N,N-dimethyl-formamide / 95 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium on activated charcoal; hydrogen / methanol / 20 °C 2: ethanol / 75 °C / Inert atmosphere 3: sodium azide / N,N-dimethyl-formamide / 95 °C / Inert atmosphere 4: ammonia / methanol / 70 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: potassium <i>tert</i>-butylate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / toluene / 6.5 h / 105 - 110 °C / Inert atmosphere 3: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 7 h / 65 - 70 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: potassium <i>tert</i>-butylate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / toluene / 6.5 h / 105 - 110 °C / Inert atmosphere 3: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 7 h / 65 - 70 °C / Inert atmosphere 4: trifluoroacetic acid / 0.17 h / 21 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 10 h / 105 - 110 °C / Inert atmosphere 3: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 7 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: potassium <i>tert</i>-butylate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / toluene / 6.5 h / 105 - 110 °C / Inert atmosphere 3: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 7 h / 65 - 70 °C / Inert atmosphere 4: trifluoroacetic acid / 0.17 h / 21 °C 5: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 5 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: potassium <i>tert</i>-butylate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / toluene / 6.5 h / 105 - 110 °C / Inert atmosphere 3: potassium <i>tert</i>-butylate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / toluene / 5 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 10 h / 105 - 110 °C / Inert atmosphere 3: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 8 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 9 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 9 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 9 h / 105 - 110 °C / Inert atmosphere 3: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 6 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 9 h / 105 - 110 °C / Inert atmosphere 3: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 6 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: potassium <i>tert</i>-butylate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate / toluene / 6.5 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 10 h / 40 - 45 °C / 3800.26 - 5320.36 Torr / Autoclave 2: tri tert-butylphosphoniumtetrafluoroborate; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 10 h / 105 - 110 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With potassium hydroxide In dimethyl sulfoxide at 100℃; for 16h; | 3.5 4.2. Typical procedure for the synthesis of 2aa General procedure: A mixture of 2-fluorobenzamide (1a, 69.5 mg, 0.5 mmol), MeOH (ca. 32.0 mg, 1.0 mmol), KOH (56.0 mg, 1.0 mmol) and DMSO (2.0 mL) in a 25 mL screw-capped thick-walled Pyrex tube was stirred at room temperature for 16 h, and then water (10 mL) was added to the reaction mixture with stirring, and the mixture was extracted with ethyl acetate three times (3 * 10 mL). The combined organic phases were dried over Na2SO4 overnight. The filtered solution was concentrated under reduced pressure, and the crude residue was purified by column chromatography on silica gel with the use of petroleum ether/ethyl acetate/trimethylamine (gradient mixture ratio from 6:1:0.05 to 2:1:0.05 in volume) to afford 2aa as a white solid in 80% yield (60.7 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85 %Chromat. | With platinum on carbon; potassium <i>tert</i>-butylate; hydrogen at 150℃; for 48h; Autoclave; | 2.4. Typical procedures of catalytic reactions General procedure: After the reduction under a flow of H2 at 300°C for 0.5h, we carried out catalytic tests without exposing the catalyst to air as follows. Methanol (30mmol) was injected to the reduced catalyst inside the glass tube through a septum inlet, thus the catalyst was covered with a layer of methanol to restrict it from air exposure. After removal of the septum under air, amine (1mmol), solid NaOH (1mmol), n-dodecane (0.25mmol) and a magnetic stirrer bar were placed in the tube. The tube was inserted into a stainless-steel autoclave (28cm3) and purged with N2 gas. Finally, the resulting mixture was heated at 150°C and stirred under 1barN2. For the model reaction of n-octylamine, the catalyst screening, optimization of reaction conditions, kinetic studies and control reactions, the conversion of n-octylamine and yields of products were determined by GC analyses, using n-dodecane as an internal standard by applying the GC sensitivity of the isolated or commercial products. For the substrate scope study, the products were isolated by column chromatography with silica gel 60 (spherical, 60-100μm, Kanto Chemical Co., Ltd.) using hexane/ethyl acetate or ethyl acetate/methanol as the eluting solvent. The yields of the isolated amine derivatives were determined and identified by 1H and 13C NMR and GC-MS methods. |
With palladium 10% on activated carbon; potassium <i>tert</i>-butylate at 150℃; for 48h; |
Tags: 16498-20-7 synthesis path| 16498-20-7 SDS| 16498-20-7 COA| 16498-20-7 purity| 16498-20-7 application| 16498-20-7 NMR| 16498-20-7 COA| 16498-20-7 structure
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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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