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Synonyms: 4'-Nitroacetophenone
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Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong , et al. JOC,2022,87(2):910-919.
Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.
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Purchased from AmBeed: 607-35-2 ; 578-66-5 ; 613-50-3 ; 100-19-6 ; 579-71-5 ; 3034-94-4 ; 5683-43-2 ; 99-92-3 ; 13534-97-9 ; 5676-60-8 ; 5470-18-8 ; 619-45-4 ; 553-26-4 ; 580-15-4 ; 611-34-7 ; 619-72-7 ; 100-13-0 ; 540-37-4 ; 1849-25-8 ; 4487-59-6 ; 555-16-8 ; 6298-19-7 ; 556-08-1 ; 953-26-4 ; 54060-30-9 ; 62-23-7 ; 607-34-1 ; 3867-18-3 ; 873-74-5 ; 3544-24-9 ; 94-52-0 ; 1520-21-4 ; 5470-34-8 ; 619-50-1 ; 586-39-0 ; 934-22-5 ; 402-54-0 ; 15411-43-5 ; 455-14-1 ; 17763-80-3 ; 3085-54-9 ; 1942-30-9 ; 1694-20-8 ; 6305-66-4 ; 41656-75-1 ; 6393-17-5 ; 4309-66-4
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CAS No. : | 100-19-6 |
Formula : | C8H7NO3 |
M.W : | 165.15 |
SMILES Code : | CC(C1=CC=C([N+]([O-])=O)C=C1)=O |
Synonyms : |
4'-Nitroacetophenone
|
MDL No. : | MFCD00007355 |
InChI Key : | YQYGPGKTNQNXMH-UHFFFAOYSA-N |
Pubchem ID : | 7487 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P280-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; phosphorus tribromide; sodium borohydrid; In ethanol; dichloromethane; | (1) Preparation of 1-(4-nitrophenyl)ethyl bromide 6.0 g of p-nitroacetophenone was dissolved in 100 ml of ethanol, and 0.75 g of sodium borohydride was added thereto under ice cooling. Afterward, the reaction solution was stirred at room temperature for 2 hours, and 1 ml of 0.1N hydrochloric acid was added thereto so as to bring the reaction to an end. This reaction mixture was concentrated under reduced pressure, and 100 ml of 0.5N hydrochloric acid was added to the resulting residue and extraction was then carried out twice with 50 ml of ether. The resulting ether layers were joined together, washed with water, and then dried over anhydrous sodium sulfate, and the solvent was distilled off. Afterward, the resulting residue was dissolved in 100 ml of methylene chloride. 7.2 g of phosphorus tribromide was added dropwise to the solution under ice cooling, followed by stirring at room temperature for 10 hours. Next, an aqueous potassium carbonate solution was added to the reaction solution to neutralize the same, and the resulting methylene chloride layer was separated, washed with water, and then dried over anhydrous sodium sulfate. Afterward, the solvent was distilled off under reduced pressure, and the resulting residue was purified through a silica gel column chromatograph (chloroform/hexane=2/1 in volume ratio), thereby obtaining 3.5 g of oily 1-(4-nitrophenyl)ethyl bromide. Analytical results of the obtained bromide derivative NMR (CDCl3) delta ppm: 2.06 (d, 3 H), 5.23 (q. 1 H), 7.60 (d, 2 H), 8.20 (d, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93%; 5% | With Oxone; In water; acetonitrile; at 20℃; for 5.5h; | General procedure: To 16 mL of acetonitrile/water (1:1 v/v) mixture was added 0.5-1.2 mmol of the starting compound. The contents were heated at reflux with introduction of oxone (cf. entries for each case) incrementally over the entire duration of the reaction. For secondary benzyl halides, the reactions were run at room temperature. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic matter was extracted with ethyl acetate. The combined organic extract was dried over anhyd Na2SO4 and concentrated in vacuo. Short pad silica gel column chromatography of the residue led to isolation of the pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | General procedure: All materials were dried for one day at 120 C. Chloride and carbonyl derivatives were introduced into a Schlenk of 30 mL. Products were put in vacuo, then under nitrogen. An appropriate volume of anhydrous DMF was added after 10 min of nitrogen bubbling. The solution was vigorously stirred for 20 min at -20 C. TDAE was added slowly under inert atmosphere. The reaction was stirred for one hour. The second reaction phase was performed at rt or at temperature according to procedure of synthesis. The reaction was hydrolysed with distilled water after TLC analysis clearly showed that the chloride 1 had been totally consumed. The aqueous solution was extracted with dichloromethane and the combined organic layers washed with brine then dried on MgSO4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In methanol; at 20℃; for 24h; | General procedure: (b) A mixture of 10 mmol of 3 and 10 mmol of substituted acetophenone (4a-h) in methanol (30 ml) was stirred at room temperature for 24 hours using 20% NaOH as a catalyst to make the solution alkaline. The reaction mixture was poured in ice cold water. The crude 3-(4-((4-fluorobenzyl)oxy)phenyl)-1-phenylprop-2-en-1-one (5a-h) was isolated and recrystallized from hot absolute ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71.3% | In ethanol;Reflux; | General procedure: solutionof acid hydrazide (0.01 mol) and appropriate benzaldehyde/acetophenone (0.01 mol) in ethanol was refluxed for 5-6 h. The precipitated title compounds were then filtered off, washed with water and recrystallized from ethanol. |
Tags: 100-19-6 synthesis path| 100-19-6 SDS| 100-19-6 COA| 100-19-6 purity| 100-19-6 application| 100-19-6 NMR| 100-19-6 COA| 100-19-6 structure
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