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577-59-3

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577-59-3 Usage

Chemical Properties

yellow-green liquid or crystals. Soluble in alcohol, ether and chloroform, slightly soluble in water.

Uses

Different sources of media describe the Uses of 577-59-3 differently. You can refer to the following data:
1. 2'-Nitroacetophenone is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. It is also used as a synthetic reagent. It is the sensitizer which can be used as pharmaceutical intermediates.
2. 2''-Nitroacetophenone (cas# 577-59-3) is a compound useful in organic synthesis. It is also used as an intermediate for photosensitive materials.?

Preparation

o-Nitroacetophenone is synthesized from o-nitroethylbenzene by oxidation. Add o-nitroethylbenzene, decanoic acid and initiator azobisisobutyronitrile into the reaction tower, and at the same time slowly pass air into the tower, keep the pressure at 0.3-0.8MPa, and control the oxidation at 120-130°C to generate 2-Nitroacetophenone.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 3631, 1978 DOI: 10.1021/jo00412a058Journal of the American Chemical Society, 105, p. 943, 1983 DOI: 10.1021/ja00342a050Synthesis, p. 228, 1988 DOI: 10.1055/s-1988-27522

Air & Water Reactions

Insoluble in water.

Fire Hazard

2-Nitroacetophenone is combustible.

Check Digit Verification of cas no

The CAS Registry Mumber 577-59-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,7 and 7 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 577-59:
(5*5)+(4*7)+(3*7)+(2*5)+(1*9)=93
93 % 10 = 3
So 577-59-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H7NO3/c10-8(6-9(11)12)7-4-2-1-3-5-7/h1-5H,6H2

577-59-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A13208)  2'-Nitroacetophenone, 97%   

  • 577-59-3

  • 10g

  • 845.0CNY

  • Detail
  • Alfa Aesar

  • (A13208)  2'-Nitroacetophenone, 97%   

  • 577-59-3

  • 50g

  • 3194.0CNY

  • Detail

577-59-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Nitroacetophenone

1.2 Other means of identification

Product number -
Other names 1-(2-nitrophenyl)ethanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:577-59-3 SDS

577-59-3Synthetic route

C11H17NO3Si
1352706-75-2

C11H17NO3Si

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With nitrogen dioxide at 20℃; for 1h;100%
acetophenone
98-86-2

acetophenone

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With calcium silicate; sulfuric acid; nitric acid at -15℃;97%
With sulfuric acid; nitric acid at -15℃;80%
With nitric acid
Multi-step reaction with 3 steps
1: pyridine / methanol / Reflux
2: silver(I) nitrite; dipotassium peroxodisulfate; palladium diacetate / 1,2-dichloro-ethane / 48 h / 130 °C / sealed tube
3: hydrogenchloride; water / diethyl ether / 24 h / 20 °C
View Scheme
2-nitro(ethylbenzene)
612-22-6

2-nitro(ethylbenzene)

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With potassium permanganate; sulfuric acid; acetic acid In water at 30 - 50℃; for 8h; Temperature; Reagent/catalyst; Cooling; Large scale;96%
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;93%
With oxygen In water for 4h; Reflux;87%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; iron(III) chloride In water; ethyl acetate at 20℃; for 10h;96%
With Montmorillonite K10; ferric nitrate In hexane at 60℃; for 7h;93%
With caesium carbonate In toluene at 110℃; for 18h;83%
2-ethynyl-1-nitrobenzene
16433-96-8

2-ethynyl-1-nitrobenzene

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With C22H20AuN3O2P(1+)*CF3O3S(1-); water; silver trifluoromethanesulfonate; acetic acid at 100℃; for 10h;94%
With potassium tetrachloroaurate(III); (S)-2-(2-(1H-benzo[d][1,2,3]triazol-1-yl)acetamido)propanoic acid; water; silver trifluoromethanesulfonate; acetic acid Schlenk technique; Inert atmosphere;88%
With methanol; [Co((dimethylglyoximate)BF2)2•2H2O] at 65℃; for 60h; Sealed tube; Neutral conditions; regioselective reaction;60%
carbon monoxide
201230-82-2

carbon monoxide

tetramethylstannane
594-27-4

tetramethylstannane

2-nitrobenzenediazonium tetrafluoroborate
365-33-3

2-nitrobenzenediazonium tetrafluoroborate

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With palladium diacetate In acetonitrile for 0.5h; Ambient temperature;93%
trimethylsiloxyethene
6213-94-1

trimethylsiloxyethene

o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In dimethyl sulfoxide; N,N-dimethyl-formamide at 20 - 100℃; for 2h; Heck Reaction; Microwave irradiation; regioselective reaction;91%
2,2-Dimethyl-5-(2-nitro-benzoyl)-[1,3]dioxane-4,6-dione

2,2-Dimethyl-5-(2-nitro-benzoyl)-[1,3]dioxane-4,6-dione

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With hydrogenchloride; water for 0.0833333h; microwave irradiation;90%
With hydrogenchloride for 4h; Heating; Yield given;
2-Nitrobenzoylessigsaeure

2-Nitrobenzoylessigsaeure

A

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

B

2-Nitrobenzoylessigsaeureethylester

2-Nitrobenzoylessigsaeureethylester

Conditions
ConditionsYield
With hydrogenchloride In ethanol at 20℃;A 8%
B 87%
ethylbenzene
100-41-4

ethylbenzene

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With cobalt(II) stearate; sodium carbonate; sodium hydroxide at 140 - 165℃; under 6000.6 Torr; for 19.5h; pH=7 - 8.5; Pressure; Temperature;85.5%
1-(2-nitro-phenyl)-ethanone oxime
10342-62-8

1-(2-nitro-phenyl)-ethanone oxime

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With perchloric acid; dihydrogen peroxide; potassium bromide; ammonium molybdate tetrahydrate In water at 20℃; for 3h;85%
With sulfuric acid
(E)-1-(2-nitrophenyl)ethanone O-methyl oxime
1262802-04-9

(E)-1-(2-nitrophenyl)ethanone O-methyl oxime

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With hydrogenchloride; water In dichloromethane at 100℃; for 24h; Sealed tube;85%
With hydrogenchloride; water In diethyl ether at 20℃; for 24h;84%
C18H23NO7

C18H23NO7

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With sulfuric acid; acetic acid In water Reflux;80.5%
acetophenone
98-86-2

acetophenone

A

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

B

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With trifluoromethylsulfonic anhydride; ethylammonium nitrate at 0 - 20℃; for 2h; Inert atmosphere;A n/a
B 77%
With aluminium trinitrate; acetic anhydride; scandium tris(trifluoromethanesulfonate) In acetonitrile at 20℃; for 24h;A 6%
B 12%
With Nitrogen dioxide; ozone In dichloromethane at -10℃; Mechanism; Product distribution; var. time; other ketones and benzaldehyde;
2-nitrobenzenesulfonyl hydrazide
5906-99-0

2-nitrobenzenesulfonyl hydrazide

acetonitrile
75-05-8

acetonitrile

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With 1,10-Phenanthroline; water; palladium diacetate at 100℃; under 760.051 Torr; for 6h;74%
o-nitroiodobenzene
609-73-4

o-nitroiodobenzene

triethylamine
121-44-8

triethylamine

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With water; oxygen; zinc(II) oxide In acetonitrile at 20℃; Irradiation;64%
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

A

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

B

(+/-)-2-(2-nitrophenyl)oxirane
39830-70-1

(+/-)-2-(2-nitrophenyl)oxirane

Conditions
ConditionsYield
In diethyl ether 1.) 0 deg C 1 h: 2.) 3 h room temperature;A 14%
B 61%
Z-2-<1-Hydroxy-1-(2-nitrophenyl)methylen>acetessigsaeureethylester
104765-26-6

Z-2-<1-Hydroxy-1-(2-nitrophenyl)methylen>acetessigsaeureethylester

A

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

B

4-hydroxy-4-(2-nitrophenyl)but-3-en-2-one
60143-82-0

4-hydroxy-4-(2-nitrophenyl)but-3-en-2-one

Conditions
ConditionsYield
With sulfuric acid In water for 5h; Heating;A 61%
B 25%
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

A

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

B

(+/-)-2-(2-nitrophenyl)oxirane
39830-70-1

(+/-)-2-(2-nitrophenyl)oxirane

Trimethyl-[(2R,3R)-3-(2-nitro-phenyl)-oxiranyl]-silane

Trimethyl-[(2R,3R)-3-(2-nitro-phenyl)-oxiranyl]-silane

Conditions
ConditionsYield
With triethylamine In methanol; diethyl ether for 26h; Ambient temperature;A 8%
B 52%
C 14%
C11H13NO2S2

C11H13NO2S2

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With water In 1,4-dioxane at 110℃; for 2h; Inert atmosphere; Microwave irradiation;52%
2-nitrophenyl bromide
577-19-5

2-nitrophenyl bromide

triethylamine
121-44-8

triethylamine

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With water; oxygen; zinc(II) oxide In acetonitrile at 20℃; Irradiation;49%
2-aminoacetophenone
551-93-9

2-aminoacetophenone

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 2h; Reflux;43%
2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With diethyl ether at -10℃;
Acetaldehyde oxime
107-29-9

Acetaldehyde oxime

2-Nitrophenyldiazonium
25910-37-6

2-Nitrophenyldiazonium

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With sodium acetate; copper(II) sulfate; sodium sulfite in wss. Loesung und anschl. mit wss. HCl;
o-nitrocumene
6526-72-3

o-nitrocumene

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
Erhitzen mit Luft;
ethyl (2-nitrobenzoyl)acetate
52119-39-8

ethyl (2-nitrobenzoyl)acetate

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With sulfuric acid; water
2-Nitrobenzoylessigsaeure
22751-16-2

2-Nitrobenzoylessigsaeure

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
durch Vakuumdestillation;
2-Nitrobenzoylessigsaeure
22751-16-2

2-Nitrobenzoylessigsaeure

A

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

B

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

Conditions
ConditionsYield
bei der Destillation im Vakuum;
diethyl 2-(2-nitro-benzoyl)malonate
106718-56-3

diethyl 2-(2-nitro-benzoyl)malonate

2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With sulfuric acid; acetic acid
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate In 1,4-dioxane at 20℃; for 0.5h;100%
With C40H37ClN2PRuS(1+)*C24H20B(1-); isopropyl alcohol; potassium hydroxide at 82℃; for 2h; Catalytic behavior;100%
With sodium tetrahydroborate In 1,4-dioxane; methanol at 0 - 20℃; for 1h;99%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

3-(dimethylamino)-1-(2-nitrophenyl)prop-2-en-1-one
87488-61-7

3-(dimethylamino)-1-(2-nitrophenyl)prop-2-en-1-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100 - 110℃; for 2h;100%
In N,N-dimethyl-formamide at 100℃; for 0.833333h;95%
In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;90%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

4-(2-nitrophenyl)-2,4-dioxobutanoic acid ethyl ester
178114-28-8

4-(2-nitrophenyl)-2,4-dioxobutanoic acid ethyl ester

Conditions
ConditionsYield
With sodium ethanolate In tetrahydrofuran at 0℃; for 2h;99%
Stage #1: oxalic acid diethyl ester With sodium methylate In diethyl ether at 20℃; Inert atmosphere;
Stage #2: 2-acetylnitrobenzene In diethyl ether at 20℃; for 12h;
86%
With sodium ethanolate In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;78%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

Conditions
ConditionsYield
With D-glucose In aq. phosphate buffer at 25℃; for 24h; pH=7.0; stereoselective reaction;99%
With Debaryomyces hansenii P1 at 30℃; for 48h; pH=5.5; Microbiological reaction; enantioselective reaction;87%
With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole In dichloromethane at -78℃; for 24h; Inert atmosphere;74%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

benzaldehyde
100-52-7

benzaldehyde

4-methyl-2-phenylquinazoline
1806-66-2

4-methyl-2-phenylquinazoline

Conditions
ConditionsYield
With ammonium formate In 1,4-dioxane; water at 60℃; for 6h; Catalytic behavior; Temperature; Time; Reagent/catalyst; Sealed tube; Green chemistry;99%
Stage #1: 2-acetylnitrobenzene; benzaldehyde In water at 60℃; for 0.0833333h;
Stage #2: With borane-ammonia complex In water at 60℃; for 8h; Catalytic behavior; Temperature; Time; Reagent/catalyst;
99%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

4-(4-methylquinazolin-2-yl)benzonitrile

4-(4-methylquinazolin-2-yl)benzonitrile

Conditions
ConditionsYield
With ammonium formate In 1,4-dioxane; water at 60℃; for 6h; Sealed tube; Green chemistry;99%
Stage #1: 2-acetylnitrobenzene; 4-cyanobenzaldehyde In water at 60℃; for 0.0833333h;
Stage #2: With borane-ammonia complex In water at 60℃; for 8h;
97%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

diethyl cyanophosphonate
2942-58-7

diethyl cyanophosphonate

lithium cyanide
2408-36-8

lithium cyanide

1-cyano-1-(2-nitrophenyl)ethyl diethylphosphate

1-cyano-1-(2-nitrophenyl)ethyl diethylphosphate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.0833333h;99%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

2-aminoacetophenone
551-93-9

2-aminoacetophenone

Conditions
ConditionsYield
With potassium hydroxide In isopropyl alcohol at 100℃; Microwave irradiation;98%
With formic acid; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; triethylamine; potassium iodide In dimethyl sulfoxide at 100℃; for 20h; Inert atmosphere; chemoselective reaction;97%
With 1-methylcyclohex-1-ene; palladium on activated charcoal In methanol at 80℃; for 0.166667h; microwave irradiation;95%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

trans-3-(4-chlorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one
69511-65-5

trans-3-(4-chlorophenyl)-1-(2-nitrophenyl)prop-2-en-1-one

Conditions
ConditionsYield
With acetic acid In ethanol Aldol Condensation;98%
With sodium hydroxide In ethanol; water at 20℃; for 12h;98%
With potassium hydroxide In methanol; water91%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

(2E)-3-(4-methylphenyl)-1-(2-nitrophenyl)-2-propen-1-one
244610-62-6

(2E)-3-(4-methylphenyl)-1-(2-nitrophenyl)-2-propen-1-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 0℃; for 3h; Aldol condensation; Inert atmosphere;97%
With acetic acid In ethanol Aldol Condensation;97%
With sodium hydroxide In ethanol; water at 20℃; for 12h;97%
With potassium hydroxide In methanol; water93%
With magnesium oxide In o-xylene at 90℃; for 8h; Claisen-Schmidt Condensation; Inert atmosphere;80 %Chromat.
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

benzaldehyde
100-52-7

benzaldehyde

aniline
62-53-3

aniline

1-(2-nitrophenyl)-3-phenyl-3-(phenylamino)propan-1-one

1-(2-nitrophenyl)-3-phenyl-3-(phenylamino)propan-1-one

Conditions
ConditionsYield
With C11H18N3O2(1+)*C2F3O2(1-) In neat (no solvent) at 20℃; for 2h; Mannich Aminomethylation;97%
With graphene oxide In ethanol at 20℃; for 5h; Mannich Aminomethylation; Green chemistry;90%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

2-Chloroanisole
766-51-8

2-Chloroanisole

C15H13NO4

C15H13NO4

Conditions
ConditionsYield
With C34H36ClN3Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 4h; Reagent/catalyst;97%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

1-chloro-3-methoxy-benzene
2845-89-8

1-chloro-3-methoxy-benzene

C15H13NO4

C15H13NO4

Conditions
ConditionsYield
With C48H64ClN3Pd; sodium t-butanolate In 1,4-dioxane at 100℃; for 4h; Reagent/catalyst;97%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

benzaldehyde
100-52-7

benzaldehyde

2'-nitro-chalcone
16619-38-8

2'-nitro-chalcone

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 0℃; for 3h;96%
With sodium methylate In ethanol for 3h; Ambient temperature;88%
With sodium hydroxide; ethanol
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

benzaldehyde
100-52-7

benzaldehyde

(2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one
53744-32-4

(2E)-1-(2-nitrophenyl)-3-phenyl-2-propen-1-one

Conditions
ConditionsYield
With acetic acid In ethanol Aldol Condensation;96%
With sodium hydroxide In ethanol at 0℃; for 3h; Aldol condensation; Inert atmosphere;95%
Stage #1: 2-acetylnitrobenzene With potassium hydroxide In ethanol; water at 0 - 20℃; for 0.5h;
Stage #2: benzaldehyde In ethanol; water at 20℃; for 3h;
83%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

2-phenyl-1H-indol-3-carboxaldehyde
25365-71-3

2-phenyl-1H-indol-3-carboxaldehyde

(E)-1-(2-Nitro-phenyl)-3-(2-phenyl-1H-indol-3-yl)-propenone
151390-85-1

(E)-1-(2-Nitro-phenyl)-3-(2-phenyl-1H-indol-3-yl)-propenone

Conditions
ConditionsYield
With piperidine In ethanol for 2h; Heating;96%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-methyl-2-(4-methylphenyl)quinazoline
1400697-35-9

4-methyl-2-(4-methylphenyl)quinazoline

Conditions
ConditionsYield
With ammonium formate In 1,4-dioxane; water at 60℃; for 6h; Sealed tube; Green chemistry;96%
Stage #1: 2-acetylnitrobenzene; 4-methyl-benzaldehyde In water at 60℃; for 0.0833333h;
Stage #2: With borane-ammonia complex In water at 60℃; for 8h;
95%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

1-(2-aminophenyl)ethanol
941706-81-6

1-(2-aminophenyl)ethanol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol; water at 45℃; for 2h; Green chemistry;95%
With sodium tetrahydroborate; water at 0 - 20℃; for 5h;95%
With sodium tetrahydroborate; pyrographite In tetrahydrofuran; water at 50 - 60℃; for 3h;90%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

3-methylbenzo[c]isoxazole
4127-53-1

3-methylbenzo[c]isoxazole

Conditions
ConditionsYield
With 2-bromo-2-nitropropane; indium In methanol; water at 50℃; for 0.333333h; Reduction; cyclisation;95%
With hydrogen In toluene at 30℃; under 6750.68 Torr; for 1h; Catalytic behavior; Reagent/catalyst; Autoclave; chemoselective reaction;94%
With tin(II) chloride dihdyrate In methanol; ethyl acetate at 20℃; Inert atmosphere;93%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

2-bromo-1-(2-nitrophenyl)ethanone
6851-99-6

2-bromo-1-(2-nitrophenyl)ethanone

Conditions
ConditionsYield
With aluminium trichloride; bromine In diethyl ether95%
With bromine; copper(ll) bromide In chloroform; ethyl acetate at 80℃;91.8%
With aluminum (III) chloride; bromine In diethyl ether at 0 - 20℃; for 4h; Inert atmosphere;88%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

hydrazone of 2-nitroacetophenone
116271-34-2

hydrazone of 2-nitroacetophenone

Conditions
ConditionsYield
With hydrazine hydrate; acetic acid In ethanol; water for 3h; Heating;95%
With hydrazine hydrate; acetic acid In ethanol at 80℃; for 1h; Reflux;95%
With hydrazine hydrate; acetic acid In ethanol for 3h; Reflux;81%
With hydrazine hydrate; acetic acid In ethanol for 4h; Reflux;49.3%
With hydrazine hydrate In ethanol Reflux;
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

(E)-3-(N,N-dimethylamino)-1-(2-nitrophenyl)-2-propen-1-one
153813-81-1

(E)-3-(N,N-dimethylamino)-1-(2-nitrophenyl)-2-propen-1-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 0.75h; Inert atmosphere;95%
In toluene at 110℃; Inert atmosphere;95%
In N,N-dimethyl-formamide at 100℃; for 8h;88%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

(E)-1-(2-nitrophenyl)-3-(4-bromophenyl)-2-propen-1-one

(E)-1-(2-nitrophenyl)-3-(4-bromophenyl)-2-propen-1-one

Conditions
ConditionsYield
With acetic acid In ethanol Aldol Condensation;95%
With sodium hydroxide; ethanol
With sodium hydroxide In ethanol; water at 20℃;
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

o-nitroacetophenone O-methyl oxime
288591-69-5

o-nitroacetophenone O-methyl oxime

Conditions
ConditionsYield
In pyridine; ethanol for 8h; Condensation; Heating;95%
With pyridine In ethanol for 3h; Molecular sieve; Heating / reflux;87%
With pyridine In ethanol at 60℃; for 6h;
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

C22H18N4O4
1235974-13-6

C22H18N4O4

Conditions
ConditionsYield
With silica gel-supported sulfuric acid In methanol at 20℃; for 0.833333h;95%
2-acetylnitrobenzene
577-59-3

2-acetylnitrobenzene

3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

(2E)-3-(3,4-dimethoxyphenyl)-1-(2-nitrophenyl)-2-propen-1-one

(2E)-3-(3,4-dimethoxyphenyl)-1-(2-nitrophenyl)-2-propen-1-one

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 0℃; for 3h; Aldol condensation; Inert atmosphere;95%
With sodium hydroxide In ethanol; water at 20℃; for 12h;91%
With potassium hydroxide In ethanol; water at 0 - 25℃; Claisen-Schmidt Condensation; Inert atmosphere;83%
With sodium hydroxide In ethanol; water at 20℃;75%
With sodium hydroxide In ethanol; water at 20℃;

577-59-3Relevant articles and documents

Selective electrochemical oxidation of aromatic hydrocarbons and preparation of mono/multi-carbonyl compounds

Li, Zhibin,Zhang, Yan,Li, Kuiliang,Zhou, Zhenghong,Zha, Zhenggen,Wang, Zhiyong

, p. 2134 - 2141 (2021/09/29)

A selective electrochemical oxidation was developed under mild condition. Various mono-carbonyl and multi-carbonyl compounds can be prepared from different aromatic hydrocarbons with moderate to excellent yield and selectivity by virtue of this electrochemical oxidation. The produced carbonyl compounds can be further transformed into α-ketoamides, homoallylic alcohols and oximes in a one-pot reaction. In particular, a series of α-ketoamides were prepared in a one-pot continuous electrolysis. Mechanistic studies showed that 2,2,2-trifluoroethan-1-ol (TFE) can interact with catalyst species and generate the corresponding hydrogen-bonding complex to enhance the electrochemical oxidation performance. [Figure not available: see fulltext.]

Decatungstate-mediated solar photooxidative cleavage of CC bonds using air as an oxidant in water

Du, Dongdong,Luo, Junfei,Shi, Sanshan,Xie, Pan,Xue, Cheng

, p. 5936 - 5943 (2021/08/23)

With the increasing attention for green chemistry and sustainable development, there has been much interest in searching for greener methods and sources in organic synthesis. However, toxic additives or solvents are inevitably involved in most organic transformations. Herein, we first report the combination of direct utilization of solar energy, air as the oxidant and water as the solvent for the selective cleavage of CC double bonds in aryl olefins. Various α-methyl styrenes, diaryl alkenes as well as terminal styrenes are well tolerated in this green and sustainable strategy and furnished the desired carbonyl products in satisfactory yields. Like heterogeneous catalysis, this homogeneous catalytic system could also be reused and it retains good activity even after repeating three times. Mechanism investigations indicated that both O2- and 1O2 were involved in the reaction. Based on these results, two possible mechanisms, including the electron transfer pathway and the energy transfer pathway, were proposed.

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

Gong, Pei-Xue,Xu, Fangning,Cheng, Lu,Gong, Xu,Zhang, Jie,Gu, Wei-Jin,Han, Wei

supporting information, p. 5905 - 5908 (2021/06/18)

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

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