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CAS No. : | 619-26-1 | MDL No. : | MFCD00963641 |
Formula : | C7H8N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IKSRCCUOUJJGAU-UHFFFAOYSA-N |
M.W : | 152.15 | Pubchem ID : | 219622 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H317 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Stage #1: 3-nitro-aniline With trifluoroacetic anhydride In 1,2-dichloro-ethane at 0℃; for 1h; Stage #2: methyl iodide With potassium carbonate In butanone at 60℃; for 2h; Stage #3: With methanol; potassium carbonate at 20℃; for 1h; | |
29% | With potassium carbonate In acetone at 50℃; | 14.1 Step 1: N-methyl-3-nitroaniline Step 1: N-methyl-3-nitroaniline To a solution of 3-nitrobenzenamine (5 g 36.2 mmol) in acetone (30 mL) were added iodomethane (5.65 g, 39.8 mmol) and potassium carbonate (10 g, 72.4 mmol). The mixture was stirred at 50°C overnight. The mixture was concentrated to dryness under reduced pressure. The residue was purified by column chromatography (petroleum ether:ethylacetate, 10:1) to give N-methyl-3-nitroaniline (1.6 g, 29%) as a red solid. LCMS (Method B): 3.01 mm [MH]= 153.1. |
With sodium hydroxide; ethanol |
at 110℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | In 1,4-dioxane for 1h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In toluene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With toluene-4-sulfonic acid In toluene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With pyridine In toluene for 12h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; | ||
In ethanol at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; | ||
In ethanol at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; | ||
In ethanol at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With sodium hydroxide; tetrabutyl-ammonium chloride In toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With nitric acid; acetic anhydride at 20℃; for 0.5h; | |
With hydroxamic acid; nitric acid In acetic anhydride at 20℃; | ||
With hydroxamic acid; nitric acid; acetic anhydride at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With triethylamine In chloroform at 20℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triethylamine In toluene at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With triethylamine In toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With triethylamine In toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With potassium carbonate In acetonitrile at 20℃; for 20h; Inert atmosphere; | |
70% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With trimethylaluminum In toluene at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 70 percent / anhydrous potassium carbonate / acetone / Heating 2.1: m-chloroperbenzoic acid / CHCl3 / 0.33 h / 0 - 5 °C 2.2: 95 percent / CHCl3 / 10 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 85 percent / Et3N / toluene / 3 h / 20 °C 2: 64 percent / t-BuOK / dimethylsulfoxide / 0.67 h / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / Et3N / toluene / 20 °C 2: 9 percent / t-BuOK / dimethylsulfoxide / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / Et3N / toluene / 20 °C 2: 56 percent / t-BuOK / dimethylsulfoxide / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 75 percent / Et3N / toluene / 20 °C 2: 12 percent / t-BuOK / dimethylsulfoxide / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 75 percent / Et3N / toluene / 20 °C 2: 45 percent / t-BuOK / dimethylsulfoxide / 22 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 79 percent / Et3N / CHCl3 / 4 h / 20 °C 2: 75 percent / 1 M aq. NaOH / methanol / 2 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: 79 percent / Et3N / CHCl3 / 4 h / 20 °C 2.1: 75 percent / 1 M aq. NaOH / methanol / 2 h / 20 °C 3.1: CDI / dimethylformamide / 1 h / 0 °C 3.2: 77 percent / Et3N / dimethylformamide / 16 h / 20 °C 4.1: 96 percent / H2 / 10 percent Pd/C / methanol / 5 h / 20 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 79 percent / Et3N / CHCl3 / 4 h / 20 °C 2.1: 75 percent / 1 M aq. NaOH / methanol / 2 h / 20 °C 3.1: CDI / dimethylformamide / 1 h / 0 °C 3.2: 77 percent / Et3N / dimethylformamide / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 79 percent / Et3N / CHCl3 / 4 h / 20 °C 2.1: 75 percent / 1 M aq. NaOH / methanol / 2 h / 20 °C 3.1: CDI / dimethylformamide / 1 h / 0 °C 3.2: 77 percent / Et3N / dimethylformamide / 16 h / 20 °C 4.1: 96 percent / H2 / 10 percent Pd/C / methanol / 5 h / 20 °C / 760 Torr 5.1: 64 percent / acetonitrile / 16 h / 10 °C 6.1: 76 percent / 1 M aq. NaOH / ethanol / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 79 percent / Et3N / CHCl3 / 4 h / 20 °C 2.1: 75 percent / 1 M aq. NaOH / methanol / 2 h / 20 °C 3.1: CDI / dimethylformamide / 1 h / 0 °C 3.2: 77 percent / Et3N / dimethylformamide / 16 h / 20 °C 4.1: 96 percent / H2 / 10 percent Pd/C / methanol / 5 h / 20 °C / 760 Torr 5.1: 64 percent / acetonitrile / 16 h / 10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 78 percent / pyridine / toluene / 12 h / Ambient temperature 2: 94 percent / toluene / Ambient temperature 3: 77 percent / 1 N NaOH / H2O / 0.5 h / Ambient temperature 4: 70 percent / CHCl3 / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 78 percent / pyridine / toluene / 12 h / Ambient temperature 2: 94 percent / toluene / Ambient temperature 3: 77 percent / 1 N NaOH / H2O / 0.5 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 13.a a) N-(3-Nitrophenyl)-N-methylacetamideTo a solution of 3-nitro-λ/-methylaniline (650 mg, 4.27 mmol) in CH2CI2 (10 ml_) under Ar-atmosphere, acetyl chloride (0.33 ml_, 4.7 mmol), a catalytic amount of DMAP and DIEA (1.49 ml_, 8.5 mmol) were added. The resulting mixture was stirred at room temperature overnight. The resulting residue was diluted with H2O, the phases were separated and the aqueous phase extracted with CH2CI2. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product thus obtained was directly used in the next step. LC-MS (method 5): tR = 1 .43 min; m/z = 195 (MH+). | |
In dichloromethane at 20℃; | 3.a To a solution of 3-nitro-λ/-methylaniline (650 mg, 4.27 mmol) in CH2CI2 (10 ml_) under Ar-atmosphere, acetyl chloride (0.33 ml_, 4.7 mmol), a catalytic amount of DMAP and DIEA (1.49 ml_, 8.5 mmol) were added. The resulting mixture was stirred at room temperature overnight. The resulting residue was diluted with H2O, the phases were separated and the aqueous phase extracted with CH2CI2. The combined organic phases were dried over Na2SO4 and concentrated to dryness. The crude product thus obtained was directly used in the next step. LC-MS (method 5): tR = 1.43 min; m/z = 195 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.1% | With copper In water at 100℃; for 12h; | |
84% | In water for 4h; Reflux; | Synthesis of N-methyl-3-nitroaniline (Precursor-02): (00071] To a stirred suspension of 1-bromo-3-nitrobenzene 9 (5.0 g, 24.75 mmol) and methyl amine (3.8g, 3123.7 mmol) in water (7.0 mL), copper powder (0.079g, 1.23 mmol) was charged and put on reflux for 4 hour. The crude reaction mixture was diluted with ethyl acetate (30 mL) and water (20 mL). The organic layer was dried (Na2SO4), filtered and evaporated to afford N-methyl-3 -nitroaniline precursor-02: (3.1 g, 84% yield) as yellow solid. ‘HNMR (400 MHz, DMSO-d6): ö 7.32-7.34 (m, 2H), 7.27 (s, 1H),7.27(s, 1H), 6.41(d, 1H), 2.73 (d, 3H). MS: 153.10 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 4-aminopyridine In tetrahydrofuran at 25℃; for 3h; | 5 Example 5 [2-(4-Iodo-2-methoxy-pyridin-3-yl)-lH-indol-6-yl]-methyl-amine A solution of N-methyl-3-nitroaniline (1.00 g, 6.57 mmol), di-tert-butyl dicarbonate (1.43 g, 6.57 mmol) and pyridine-4-ylamine (619 mg, 6.57 mmol) in THF (50 mL) was stirred at 25°C for 3 h. The reaction mixture was concentrated in vacuo, then added ethyl acetate (50 mL). The organic solution was washed three times with water and once with brine. The organic layer was then dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (80/20 hexanes/ethyl acetate) afforded methyl-(3-nitro-phenyl)-carbamic acid tert-butyl ester (1.60g, 97%) as an oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 0.333333h; Cooling with ice; | N-Acylation of anilines with ω-bromoalkanoyl chlorides. General procedure for ω-bromoalkanamido derivatives 7a-c, 12a-i and 15a-d The suitable ω-bromoalkanoyl chloride (0.7 mmol) was added dropwise to a stirred ice-cooled solution of the suitable aniline (0.33 mmol) and NaHCO3 (0.10 g, 1.22 mmol) in EtOAc (0.4 mL) and water (0.4 mL), and the resulting mixture was stirred at room temperature for 20 min. Water was added and the aqueous phase was extracted three times with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford a crude residue that was used for the next step, without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 0.333333h; Cooling with ice; | N-Acylation of anilines with ω-bromoalkanoyl chlorides. General procedure for ω-bromoalkanamido derivatives 7a-c, 12a-i and 15a-d The suitable ω-bromoalkanoyl chloride (0.7 mmol) was added dropwise to a stirred ice-cooled solution of the suitable aniline (0.33 mmol) and NaHCO3 (0.10 g, 1.22 mmol) in EtOAc (0.4 mL) and water (0.4 mL), and the resulting mixture was stirred at room temperature for 20 min. Water was added and the aqueous phase was extracted three times with EtOAc. The combined organic phases were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to afford a crude residue that was used for the next step, without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 44% 2: 43% | With magnesium(II) perchlorate; [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); oxygen In 1,2-dichloro-ethane at 20℃; for 38h; Molecular sieve; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]; bis[2-(diphenylphosphino)phenyl] ether; lithium tert-butoxide at 100℃; for 24h; | |
92% | Stage #1: methanol; 3-nitro-aniline With formaldehyd; sodium methylate at 20℃; for 3h; Inert atmosphere; Stage #2: With sodium tetrahydroborate for 3h; Inert atmosphere; Reflux; | 2.7 [00516] To a solution of 3-nitroaniline (2.07 g, 15 mmol) and (HCHO)n (675 mg) in MeOH (50mL) was added NaOMe (4.05 g, 75 mmol) uner N2 atmosphere. The resulting suspension wasstirred at r.t. for 3 hrs before introducing NaBH4 (570 mg, 15 mmol). The reaction mixture wasthen heated to reflux for 3 hrs. The solvent was removed under vacuum and the residue waspartitioned between EA (100 mL) and water (100 mL). The layers were separated, the organiclayer was dried over Na2S04 and concentrated in vacuo. The residue was purified by columnchromatography (silica gel, 0 to 10% ethyl acetate in petroleum ether) to provide N-methyl-3-nitroaniline (7) (2.11 g, 92%) as a white solid. |
87% | With C19H37IrN4(2+)*2I(1-); potassium carbonate at 120℃; for 17h; Inert atmosphere; Schlenk technique; Sealed tube; | N-Monomethylation of a Variety of Aromatic Amines with Methanol Catalyzed by 4c Shown in Scheme 1; General Procedure General procedure: In a stainless reactor bomb, the respective aromatic amine (1.0mmol), 4c (0.50 mol%), K2CO3 (5.0 mol%), and MeOH (1.0 mL) were placed. Then, the reactor was sealed with a stainless stopper, and the mixture was stirred for 17 h at 120 °C. After removing MeOH under reduced pressure, the products were isolated by silica gel column chromatography. |
50 %Chromat. | With potassium <i>tert</i>-butylate at 160℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triethylamine In dichloromethane at 0 - 20℃; | 2.8 [00517] At 0 °C, to a solution ofN-methyl-3-nitroaniline (7) (2.11 g, 13.87 mmol) and TEA(4.21 g, 41.60 mmol) in DCM (50 mL) was added acryloyl chloride (1.51 g, 16.64 mmol). Theresulting mixture was stirred at r.t. overnight and was then quenched with water (20 mL). Theproduct was extracted with DCM (10 mL X 2). The combined organic layer was washed withbrine, dried over Na2S04 and purified by column chromatography (silica gel, 0 to 35% ethylacetate in petroleum ether) to provide N-methyl-N-(3-nitrophenyl)acrylamide (8) (1.809 g, 63%)as an oil. LC-MS (ESI) m/z (M+1) 207.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: bis(trichloromethyl) carbonate In hexane at 20℃; for 16h; Stage #2: N-methyl-3-nitroaniline With triethylamine In tetrahydrofuran; hexane at 0 - 20℃; for 2h; | |
With pyridine In dichloromethane at 0 - 5℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With N-ethyl-N,N-diisopropylamine In ethanol for 4h; Reflux; | 8 Synthesis of 2,5-dichloro-N-methyl-N-(3-nitrophenyl)pyrimidin-4-amine (106) To a stirred suspension of N-methyl-3-nitroaniline precursor-02 (0.50 g,3.28 mmol) and 2,4,5-trichloropyrimidine 77 (0.724 g, 3.94 mmol) in ethanol (7.0 mL),DIPEA (0.85 g, 6.57 mmol) was charged and refluxed for 4 hour. The reaction mixturewas evaporated to dryness. The crude mixture was diluted with EtOAc (30 mL) andwater (20 mL). The organic layer was dried (Na2SO4), filtered and evaporated to afford 2,5-dichloro-N-methyl-N-(3 -nitrophenyl)pyrimidin-4-amine 106 (0.4 g, 41% yield) asyellow solid. MS: 299.10 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With copper diacetate; palladium dichloride; Trimethylacetic acid In acetonitrile at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | In chloroform at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-methyl-3-nitroaniline With n-butyllithium In tetrahydrofuran at -10℃; for 5h; Stage #2: prenyl bromide In tetrahydrofuran at 0℃; for 0.5h; | General Procedure for The preparation of all substrates (preparation of 1a) General procedure: To the solution of N-methylaniline (10 mmol, 1.07g) in THF, was added dropwise the n-BuLi (11mL, 1M) over 5 minutes at -10. The solution of allyl bromide (1.44g, 1.2 eq.) in THF was added slowly into the above mixture at 0°. The system was stirred for 30 minutes and quenched with a saturated aqueous ammonium chloride. The aqueous phase was extracted with ethyl acetate (3 x25 mL). The combined organic phases were washed with brine and dried over Na2SO4. After the concentration, the flash column chromatography of the residue afforded 1a in 92% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With potassium carbonate In N,N-dimethyl-formamide at 130℃; for 3h; | 14.2 Step 2: 2-chloro-N-methyl-N-(3-nitrophenyl)pyrimidin-4-am me Step 2: 2-chloro-N-methyl-N-(3-nitrophenyl)pyrimidin-4-am me To a solution of N-methyl-3-nitrobenzenamine (1.6 g, 10.5 mmol) in N,N-Dimethyl formamide (10 mL) were added 2,4-dichloropyridine (1.72 g, 11.6 mmol) and potassium carbonate (2.18 g, 15.8 mmol). The mixture was stirred at 130°C for 3 hours. The reaction mixture was then partitioned between ethyl acetate and water, the organic layer was separtated and washed with water, brine, dried over sodium sulfate andconcentrated to give a residue which was purified by column chromatography (petroleum ether:ethylacetate, 5:1) to give 2-chloro-N-methyl-N-(3-nitrophenyl)pyrim idin4-amine (1.0 g, 36%) as a light yellow solid. LCMS (Method B): 3.01 mm [MH] = 265.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | Stage #1: (E)-4-(cyclopropyl(methyl)amino)but-2-enoic acid hydrochloride salt With oxalyl dichloride; N,N-dimethyl-formamide In acetonitrile Stage #2: N-methyl-3-nitroaniline In dichloromethane at 0℃; for 0.5h; | 38 Preparation of (E)-4-(cyclopropyl(methyl)amino)-N-methyl-N-(3-nitrophenyl)but-2-enamide (505-3) (£)-4-(Cyclopropyl(methyl)amino)-N-methyl-N-(3-nitrophenyl)but-2-enamide (505-3) (200 mg, 50%) was obtained as a white solid from N-methyl-3-nitroaniline (505-2) (210 mg, 1.38 mmol) and (E)-4- (cyclopropyl(methyl)amino)but-2-enoic acid hydrochloride (397 mg, 2.07 mmol), following a similar procedure outlined in Ex.1. LC-MS (ESI): m/z (M+l) 290.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | Stage #1: formaldehyd; 3-nitro-aniline In methanol for 2h; Reflux; Stage #2: With sodium cyanoborohydride In methanol at 0 - 20℃; for 1h; | 38 Preparation of N-methyl-3-nitroaniline (505-2) N-Methyl-3-nitroaniline (505-2) (210 mg, 19%) was obtained as a yellow solid from 3- nitroaniline (505-1) (1 g, 7.25 mmol), following a similar procedure outlined in Ex. 29. LC-MS (ESI): m/z (M+l) 153.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With air In 1,2-dimethoxyethane at 20℃; Irradiation; | |
72% | Stage #1: N,N-dimethyl-3-nitroaniline With 1,4-diaza-bicyclo[2.2.2]octane; rose bengal; acetic acid In acetonitrile at 20℃; for 6h; Flow reactor; Irradiation; Stage #2: With sulfuric acid In methanol; water at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 2: hydrogen / palladium 10% on activated carbon / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-(1,1-dimethylethyl)benzoic acid In dichloromethane at 20℃; for 24h; Inert atmosphere; Glovebox; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In acetonitrile at 90℃; for 48h; | N1,N3,N5-Trimethyl-N1,N3,N5-tris(3-nitrophenyl)benzene-1,3,5-tricarboxamide (4) 1,3,5-Benzenetricabonyl trichloride (0.250 g, 0.94 mmol, 1 eq.) was taken with N-methyl-3-nitroaniline(0.471 g, 3.10 mmol, 3.3 eq.) in CH3CN (30 ml) and set at reflux for 48 hours. The reaction mixture wasthen cooled and solvent concentrated in vacuo, obtaining a honey coloured oil. The oil was purifiedby trituration with CHCl3 and Et2O, and 7 was obtained as a pale yellow powder (0.547 g, 0.89 mmol,95%). 1H NMR H (600 MHz, DMSO-d6) 8.14 (3H, t, J = 2.1 Hz, 6-H), 8.06 (3H, ddd, J = 8.2, 2.1, 0.8 Hz,8-H), 7.49 (3H, t, J = 8.2 Hz, 9-H), 7.34 (3H, s, 10-H), 7.32 (3H, s, 1-H), 3.23 (9H, s, 4-H). 13C NMR C(151 MHz, DMSO-d6) 167.9, 148.0, 144.7, 135.7, 133.5, 130.1, 128.7, 121.5, 121.2, 37.7. HRMS (m/z)(ESI+) Calculated for C30H24N6O9Na m/z = 635.1502 [M+Na]+. Found m/z = 635.1508 [M+Na]+; IR νmax(cm-1): 3457, 1650, 1610, 1525, 1440, 1350, 687. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With potassium <i>tert</i>-butylate; C49H50Cl2Ir2N5O(1+)*F6P(1-) at 130℃; for 10h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-methyl-3-nitroaniline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: 2,4-dichloroquinazoline In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 3h; | 88.1 To a stirred solution of N-methyl-3-nitrobenzenamine (0.382 g, 2.51 mmol) in DMF (10 mL) was added 60% sodium hydride (0.120 g, 3.01 mmol) at 0 °C and the mixture was stirred for 1 h at RT, followed by the addition of 2,4-dichloroquinazoline (0.5 g, 2.51 mmol) at 0 °C. The mixture was stirred for 3 h at RT. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was diluted with ice-water. The resulting solids were filtered and dried under vacuum to give the desired product. LCMS: 315.10 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With silver hexafluoroantimonate In methanol at 60℃; for 12h; Inert atmosphere; |
Tags: 619-26-1 synthesis path| 619-26-1 SDS| 619-26-1 COA| 619-26-1 purity| 619-26-1 application| 619-26-1 NMR| 619-26-1 COA| 619-26-1 structure
[ 6149-34-4 ]
N1-(4-Nitrophenyl)benzene-1,4-diamine
Similarity: 0.94
[ 6149-34-4 ]
N1-(4-Nitrophenyl)benzene-1,4-diamine
Similarity: 0.94
[ 6149-34-4 ]
N1-(4-Nitrophenyl)benzene-1,4-diamine
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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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