4′-Nitroacetophenone

Cat.NO.:A130814 Purity:98%

Product Details of 4′-Nitroacetophenone

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

Safety of 4′-Nitroacetophenone

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of 4′-Nitroacetophenone

* 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.

Upstream synthesis route of [ 100-19-6 ]
Downstream synthetic route of [ 100-19-6 ]

[ 100-19-6 ] Synthesis Path-Upstream 1~2

1
[ 108-94-1 ]
[ 100-19-6 ]
[ 23600-83-1 ]

References:

[1] Organic Letters, 2012, vol. 14, # 7, p. 1692 – 1695.

2
[ 100-19-6 ]
[ 98-80-6 ]
[ 23600-83-1 ]

References:

[1] Angewandte Chemie – International Edition, 2019, [2] Angew. Chem., 2019, vol. 131, # 7, p. 2151 – 2155,5.

[ 100-19-6 ] Synthesis Path-Downstream 1~24

1
[ 79-46-9 ]
[ 19935-81-0 ]
[ 141-52-6 ]
[ 100-19-6 ]

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 3482,3485.

2
[ 77287-34-4 ]
[ 100-19-6 ]
[ 13382-61-1 ]

References: [1]Chemistry of Heterocyclic Compounds,1974,vol. 10,p. 1294 – 1297.

Khimiya Geterotsiklicheskikh Soedinenii,1974,vol. 10,p. 1472 – 1476.

3
[ 50-00-0 ]
[ 80567-00-6 ]
[ 100-19-6 ]
3-(2,6-dimethyl-morpholin-4-yl)-1-(4-nitro-phenyl)-propan-1-one [ No CAS ]

References: [1]Journal of Pharmaceutical Sciences,1967,vol. 56,p. 328 – 332.

4
[ 14150-94-8 ]
[ 100-19-6 ]
[ 131941-28-1 ]

References: [1]Bulletin of the Chemical Society of Japan,1990,vol. 63,p. 2820 – 2827.

5
[ 100-19-6 ]
[ 3171-46-8 ]
[ 111337-09-8 ]

References: [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 311 – 315.

Khimiya Geterotsiklicheskikh Soedinenii,1987,vol. 23,p. 370 – 375.

6
[ 100-19-6 ]
[ 64611-67-2 ]

References: [1]Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 229 – 231.
[2]Synthesis,2008,p. 3205 – 3208.
[3]Tetrahedron Letters,1981,vol. 22,p. 1283 – 1286.
[4]Journal of the Chemical Society. Perkin transactions I,1999,p. 669 – 671.
[5]Journal of Organic Chemistry,1989,vol. 54,p. 4473 – 4474.
[6]Chemische Berichte,1889,vol. 22,p. 203.
[7]Journal of Molecular Catalysis B: Enzymatic,2014,vol. 109,p. 178 – 183.
[8]Organic Letters,2016,vol. 18,p. 4526 – 4529.
[9]European Journal of Organic Chemistry,2017,vol. 2017,p. 4434 – 4438.
[10]Journal of Organic Chemistry,2019,vol. 84,p. 11945 – 11957.

7
[ 100-19-6 ]
[ 64611-67-2 ]
[ 62-23-7 ]

References: [1]Tetrahedron Letters,1992,vol. 33,p. 6065 – 6068.

9
[ 67-56-1 ]
[ 100-19-6 ]
2-[1,3]dithian-2-ylidene-3-oxo-butanamide [ No CAS ]
[ 51513-29-2 ]
[ 67395-06-6 ]
[ 2345-56-4 ]

References: [1]Synthetic Communications,2004,vol. 34,p. 4545 – 4556.

10
aqueous potassium carbonate [ No CAS ]
[ 100-19-6 ]
[ 19935-81-0 ]

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).

References: [1]Patent: US5308848,1994,A .

11
[ 19935-81-0 ]
[ 100-19-6 ]

References: [1]Synthetic Communications,2010,vol. 40,p. 1106 – 1114.
[2]Organic Letters,2012,vol. 14,p. 2414 – 2417.

12
[ 100-12-9 ]
[ 19935-81-0 ]
[ 90050-69-4 ]
[ 100-19-6 ]

References: [1]Organic Letters,2012,vol. 14,p. 2414 – 2417.

13
[ 19935-81-0 ]
[ 100-19-6 ]
[ 62-23-7 ]

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.

References: [1]Tetrahedron,2012,vol. 68,p. 9763 – 9768,6.

14
[ 31825-29-3 ]
[ 100-19-6 ]
C₁₉H₁₉NO₄ [ No CAS ]

References: [1]Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 807 – 809.

15
[ 100-19-6 ]
[ 1668-54-8 ]
[ 1465740-24-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5968 – 5970.

16
[ 15862-94-9 ]
[ 100-19-6 ]
[ 1584706-47-7 ]

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.

References: [1]European Journal of Medicinal Chemistry,2014,vol. 76,p. 445 – 459.

17
[ 56442-17-2 ]
[ 100-19-6 ]
C₂₂H₁₆FNO₄ [ No CAS ]

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.

References: [1]Journal of the Korean Chemical Society,2014,vol. 58,p. 49 – 56.

18
[ 34800-90-3 ]
[ 100-19-6 ]
C₂₀H₁₇N₃O₃ [ No CAS ]

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.