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121-89-1 Usage

Chemical Properties

white to light beige crystalline powder or yellow needle-like crystals. soluble in hot water and ether, slightly soluble in ethanol. can be volatile with water vapor.

Uses

Different sources of media describe the Uses of 121-89-1 differently. You can refer to the following data:
1. 3''-Nitroacetophenone is used as a reactant in the synthesis of fluorine based aminothiazoles with antimicrobial activity.
2. 3′-Nitroacetophenone can undergo high hydrostatic pressure-assisted reduction with Ni–Al alloy in water to form 1-(3-aminophenyl)ethanol.

Preparation

3-Nitroacetophenone is synthesized from acetophenone by nitration.Synthesis of 3-nitroacetophenone

General Description

3-nitroacetophenone is a light beige powder. It is an anthropogenic compound which is used as a synthetic intermediate in the production of dyes and other organic compounds. (NTP, 1992)

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A nitrated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Fire Hazard

Flash point data for 3-Nitroacetophenone are not available, however 3-Nitroacetophenone is probably combustible.

Purification Methods

Distil the ketone in steam and crystallise it from EtOH. [Beilstein 7 IV 656.]

Check Digit Verification of cas no

The CAS Registry Mumber 121-89-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 1 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 121-89:
(5*1)+(4*2)+(3*1)+(2*8)+(1*9)=41
41 % 10 = 1
So 121-89-1 is a valid CAS Registry Number.
InChI:InChI:1S/C8H7NO3/c1-6(10)7-3-2-4-8(5-7)9(11)12/h2-5H,1H3

121-89-1 Well-known Company Product Price

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  • Alfa Aesar

  • (A12155)  3'-Nitroacetophenone, 98+%   

  • 121-89-1

  • 250g

  • 567.0CNY

  • Detail
  • Alfa Aesar

  • (A12155)  3'-Nitroacetophenone, 98+%   

  • 121-89-1

  • 500g

  • 814.0CNY

  • Detail
  • Alfa Aesar

  • (A12155)  3'-Nitroacetophenone, 98+%   

  • 121-89-1

  • 1000g

  • 1465.0CNY

  • Detail

121-89-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-Nitroacetophenone

1.2 Other means of identification

Product number -
Other names 3’-Nitroacetophenone

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:121-89-1 SDS

121-89-1Synthetic route

m-nitroacetophenone oxime
7471-32-1

m-nitroacetophenone oxime

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
Stage #1: m-nitroacetophenone oxime With hexachlorodisilane; silica gel In toluene at 110℃; for 4h;
Stage #2: With water In toluene for 0.5h;
99%
With formic acid; silica gel for 0.0333333h; microwave irradiation;94%
With zinc chlorochromate; montmorillonite K-10 at 20℃; for 1.5h;88%
3-ethylnitrobenzene
7369-50-8

3-ethylnitrobenzene

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With nickel-doped graphene carbon nitride nanoparticles; air In ethanol at 25℃; for 8h; Irradiation; Green chemistry;98%
With oxygen In water at 25℃; for 1.5h;94%
With cobalt(II) stearate; sodium carbonate; sodium hydroxide at 140 - 165℃; under 6000.6 Torr; for 20h; pH=7 - 8.5; Pressure; Temperature;85.85%
(E)-1-(3-mitrophenyl)ethan-1-one O-methyl oxime
72278-09-2

(E)-1-(3-mitrophenyl)ethan-1-one O-methyl oxime

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 20℃; for 12h;98%
1-(3-nitrophenyl)ethanol
5400-78-2

1-(3-nitrophenyl)ethanol

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With modified o-iodoxybenzoic acid In tetrahydrofuran; water at 60℃; for 3h;96%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole In N,N-dimethyl-formamide at 25℃; for 1.5h; Catalytic behavior;96%
With oxygen; pivalaldehyde; (Me4N)[Co(L)]*2H2O (L = o-phenylenebis(N'-methyloxamidate) In acetonitrile at 20℃; for 8h;95%
m-iodonitrobenzene
645-00-1

m-iodonitrobenzene

trimethylsiloxyethene
6213-94-1

trimethylsiloxyethene

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

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;96%
4-chloro-3-nitroacetophenone
5465-65-6

4-chloro-3-nitroacetophenone

dibromodifluoromethane
75-61-6

dibromodifluoromethane

A

4-Trifluoromethyl-3-nitro-acetophenone
133391-57-8

4-Trifluoromethyl-3-nitro-acetophenone

B

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With ISOPROPYLAMIDE; copper at 100℃; for 8h;A 95%
B 5%
N,N-Dimethyl-N'-[1-(3-nitro-phenyl)-eth-(E)-ylidene]-hydrazine
5758-02-1

N,N-Dimethyl-N'-[1-(3-nitro-phenyl)-eth-(E)-ylidene]-hydrazine

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With sodium perborate In acetic acid at 50 - 60℃; for 5h;92%
3'-nitro-2-bromoacetophenone
2227-64-7

3'-nitro-2-bromoacetophenone

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With sodium disulfite; hydrogen bromide In acetic acid for 3h; Heating;92%
With decaborane; palladium on activated charcoal In methanol at 20℃; for 12h;91%
With bismuth(III) chloride; sodium tetrahydroborate In tetrahydrofuran for 4h; Ambient temperature;90.9%
3-nitrophenylacetylene
3034-94-4

3-nitrophenylacetylene

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With methanol; [Co((dimethylglyoximate)BF2)2•2H2O] at 65℃; for 49h; Sealed tube; Neutral conditions; regioselective reaction;91%
With C22H20AuN3O2P(1+)*CF3O3S(1-); water; silver trifluoromethanesulfonate; acetic acid at 100℃; for 10h;91%
With silver trifluoromethanesulfonate In water; acetic acid at 110℃; for 6h; Schlenk technique;88%
acetophenone
98-86-2

acetophenone

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With sulfuric acid; nitric acid at -10℃; for 0.166667h; Temperature;90.3%
With nitric acid; cetyltrimethylammonim bromide In acetonitrile at 24.84℃; for 2h; Micellar solution; regioselective reaction;85%
With tetrammine copper(II) sulphate; nitric acid In dichloromethane; water at 20℃; for 2h; regioselective reaction;85%
2-methyl-2-(3-nitrophenyl)-1,3-oxathiolane

2-methyl-2-(3-nitrophenyl)-1,3-oxathiolane

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With eosin Y disodium salt In acetonitrile at 20℃; for 3h; Irradiation;90%
1-(3-nitro-phenyl)-ethanone-phenylhydrazone
77635-38-2

1-(3-nitro-phenyl)-ethanone-phenylhydrazone

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With 3,3-dimethyldioxirane In acetone at 20℃; for 2h;87%
1-nitro-3-vinyl-benzene
586-39-0

1-nitro-3-vinyl-benzene

A

1-(3-nitrophenyl)ethanol
5400-78-2

1-(3-nitrophenyl)ethanol

B

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With triethylsilane; (1,2,3,4,8,9,10,11,15,16,17,18,22,23,24,25-Hexadecafluorophthalocyaninato)iron(II); oxygen In ethanol at 20℃; under 760.051 Torr; for 43h; Wacker Oxidation; Sealed tube; Green chemistry; chemoselective reaction;A 12%
B 84%
C27H23NO3
1426391-57-2

C27H23NO3

A

triphenylmethane
519-73-3

triphenylmethane

B

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With iodine In neat (no solvent) at 85℃; for 2h;A 83%
B 81%
3-nitrophenylsulfonohydrazide
6655-77-2

3-nitrophenylsulfonohydrazide

acetonitrile
75-05-8

acetonitrile

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With 1,10-Phenanthroline; water; palladium diacetate at 100℃; under 760.051 Torr; for 6h;83%
2,2-dimethyl-5-(3-nitrobenzoyl)-1,3-dioxane-4,6-dione

2,2-dimethyl-5-(3-nitrobenzoyl)-1,3-dioxane-4,6-dione

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With hydrogenchloride; water for 0.0833333h; microwave irradiation;80%
With hydrogenchloride for 4h; Heating; Yield given;
1-nitro-3-vinyl-benzene
586-39-0

1-nitro-3-vinyl-benzene

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; air; (Pd(IiPr)Cl2)2; silver trifluoromethanesulfonate In methanol at 35℃; for 24h; Wacker oxidation;79%
With manganese(IV) oxide; palladium dichloride In water; acetonitrile at 60℃; for 32h;50%
With water; oxygen; palladium dichloride
nitrobenzene
98-95-3

nitrobenzene

acetyl chloride
75-36-5

acetyl chloride

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With zinc at 82 - 84℃; for 0.05h; Friedel-Crafts acylation; microwave irradiation;79%
With iron(III) oxide at 20℃; for 0.25h; Friedel Crafts acylation; regioselective reaction;69%
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;
C18H23NO7

C18H23NO7

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With sulfuric acid; acetic acid In water Reflux;76.3%
1-nitro-3-vinyl-benzene
586-39-0

1-nitro-3-vinyl-benzene

A

3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

B

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With water; oxygen; copper(l) chloride In tetrahydrofuran at 20℃; for 48h; Reagent/catalyst; Wacker-Tsuji Olefin Oxidation;A n/a
B 76%
carbon monoxide
201230-82-2

carbon monoxide

tetramethylstannane
594-27-4

tetramethylstannane

3-nitrophenyldiazonium tetrafluoroborate
586-36-7

3-nitrophenyldiazonium tetrafluoroborate

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
palladium diacetate In acetonitrile under 6619.6 Torr; for 1.5h; Heating;70%
With palladium diacetate In acetonitrile for 0.5h; Ambient temperature;70%
m-nitrobenzene boronic acid
13331-27-6

m-nitrobenzene boronic acid

acetonitrile
75-05-8

acetonitrile

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With 1,10-Phenanthroline; nickel(II) bromide 2-methoxyethyl ether complex; sodium hydrogencarbonate In water at 100℃; for 5h; Autoclave;70%
m-nitrobenzene boronic acid
13331-27-6

m-nitrobenzene boronic acid

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; water; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine at 90℃; for 8h;68%
m-iodonitrobenzene
645-00-1

m-iodonitrobenzene

triethylamine
121-44-8

triethylamine

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With water; oxygen; zinc(II) oxide In acetonitrile at 20℃; Irradiation;66%
m-Nitroacetophenone N,N-dimethylhydrazone
5758-02-1

m-Nitroacetophenone N,N-dimethylhydrazone

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; oxygen; pivalaldehyde; (NMe4)2[Ni(Me2opba)]*4H2O In fluorobenzene at 20℃; for 20h; Oxidation;60%
m-nitrobenzene boronic acid
13331-27-6

m-nitrobenzene boronic acid

acetic anhydride
108-24-7

acetic anhydride

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
chloro(ethylene)rhodium(I) dimer In 1,4-dioxane for 16h; Heating;56%
1-(3-aminophenyl)ethanone
99-03-6

1-(3-aminophenyl)ethanone

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In chloroform for 2h; Reflux;55%
3-Bromonitrobenzene
585-79-5

3-Bromonitrobenzene

triethylamine
121-44-8

triethylamine

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

Conditions
ConditionsYield
With water; oxygen; zinc(II) oxide In acetonitrile at 20℃; Irradiation;55%
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

1-(3-aminophenyl)ethanone
99-03-6

1-(3-aminophenyl)ethanone

Conditions
ConditionsYield
With cadmium sulphide; ammonium formate In water at 20℃; for 14h; Inert atmosphere; Irradiation; Sealed tube; chemoselective reaction;100%
With water; oxalic acid; titanium(IV) oxide for 3h; Wavelength; Irradiation; Inert atmosphere; Sealed tube; Green chemistry; chemoselective reaction;100%
With hydrogen In methanol at 70℃; under 3750.38 - 7500.75 Torr; for 4h; Temperature; Reagent/catalyst; Solvent;99%
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

(R)-1-(3-nitrophenyl)ethanol
76116-24-0

(R)-1-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
With N,N'-bis[(1R,2R)-2-aminocyclohexyl]benzene-1,3-disulfonamide; water; sodium formate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer at 40℃; for 0.25h; Product distribution; Further Variations:; Catalysts; Solvents; Temperatures; Reagents;100%
With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; C22H32N4O4S2; isopropyl alcohol; potassium hydroxide at 40℃; for 5h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;95%
With (p-cymene)ruthenium(II) chloride; 1-butyl-3-({[(1R,2S)-1-hydroxy-1-phenylpropan-2-yl]amino}methyl)pyridin-1-ium bromide; sodium formate In water at 40 - 50℃; for 24h; Glovebox; Schlenk technique; Inert atmosphere; Green chemistry; enantioselective reaction;89%
toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

α-tosyloxy-m-nitroacetophenone
92554-40-0

α-tosyloxy-m-nitroacetophenone

Conditions
ConditionsYield
With potassium peroxymonosulfate; 4-tolyl iodide In water; acetonitrile at 60℃; for 3h; Inert atmosphere;100%
Stage #1: toluene-4-sulfonic acid With tert-butylbenzene; water; iodine; 3-chloro-benzenecarboperoxoic acid In 2,2,2-trifluoroethanol; acetonitrile at 20℃; Inert atmosphere;
Stage #2: 3-Nitroacetophenone In 2,2,2-trifluoroethanol; acetonitrile at 60℃; for 5h; Inert atmosphere;
95%
With ammonium iodide; 3-chloro-benzenecarboperoxoic acid; benzene In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 23h;92%
ethylene glycol
107-21-1

ethylene glycol

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

2-bromomethyl-2-(3-nitrophenyl)-1,3-dioxolane
3418-27-7

2-bromomethyl-2-(3-nitrophenyl)-1,3-dioxolane

Conditions
ConditionsYield
With N-Bromosuccinimide at 45℃; for 24h; Temperature;100%
With pol(vinylphenyltrimethylammoniumtribromide) resin at 45℃; for 24h;93%
ethylene glycol
107-21-1

ethylene glycol

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

2-chloromethyl-2-(3-nitrophenyl)-1,3-dioxolane

2-chloromethyl-2-(3-nitrophenyl)-1,3-dioxolane

Conditions
ConditionsYield
With N-chloro-succinimide at 20℃; for 24h;100%
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

1-(3-nitrophenyl)ethanol
5400-78-2

1-(3-nitrophenyl)ethanol

Conditions
ConditionsYield
With formic acid; C18H24ClIrN3 In water at 80℃; for 12h; Schlenk technique; Inert atmosphere; chemoselective reaction;99%
Stage #1: 3-Nitroacetophenone With nickel boride In water; acetonitrile at 20℃; for 0.0833333h; Green chemistry;
Stage #2: With sodium tetrahydroborate In water; acetonitrile at 20℃; for 0.0166667h; Green chemistry;
98%
With chloro-trimethyl-silane; tert-Amyl alcohol; sodium hydride; zinc(II) chloride In tetrahydrofuran at 63℃; for 0.5h;97%
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

m-ethylaniline
587-02-0

m-ethylaniline

Conditions
ConditionsYield
With palladium 10% on activated carbon; water; hydrazine hydrate In ethanol at 100℃; for 24h; Reagent/catalyst;99%
Stage #1: 3-Nitroacetophenone With hydrazine hydrate at 135℃; for 3h;
Stage #2: With potassium hydroxide at 135℃; for 24h;
96.5%
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol at 70℃; under 3102.89 Torr; for 24h;46%
phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

diethyl 1-hydroxy-1-(3-nitro)phenyl-ethylphosphonate

diethyl 1-hydroxy-1-(3-nitro)phenyl-ethylphosphonate

Conditions
ConditionsYield
With n-butyllithium In neat (no solvent) at 10℃; for 0.0833333h; Catalytic behavior; Schlenk technique; Inert atmosphere;99%
With C46H76N5Si2Sm In toluene at 20℃; Schlenk technique; Inert atmosphere;96%
With 2C6H18NSi2(1-)*C36H48N4(4-)*2Nd(3+) In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;94%
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

(S)-1-(3-nitrophenyl)ethan-1-ol
103966-65-0

(S)-1-(3-nitrophenyl)ethan-1-ol

Conditions
ConditionsYield
With (R)-2,2',6,6'-tetramethoxy-4,4'-bis(di-3,5-dimethylphenylphosphine)3,3'-bipyridine; phenylsilane; cobalt(II) diacetate tetrahydrate In toluene at 40℃; for 24h; Molecular sieve; Under air; optical yield given as %ee; enantioselective reaction;99%
With D-glucose In aq. phosphate buffer at 25℃; for 24h; pH=7.0; stereoselective reaction;99%
Stage #1: 3-Nitroacetophenone With copper acetylacetonate; (S)-Xyl-P-Phos In toluene at -20℃; for 12h;
Stage #2: With sodium hydroxide In water; toluene for 3h; optical yield given as %ee; stereoselective reaction;
95%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

3-hydroxy-1,3-bis-(3-nitro-phenyl)-propan-1-one

3-hydroxy-1,3-bis-(3-nitro-phenyl)-propan-1-one

Conditions
ConditionsYield
With sodium phosphate In methanol at 25 - 32℃; for 0.166667h; ultrasonic irradiation;99%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

2-(3-nitrophenyl)-2-((trimethylsilyl)oxy)propanenitrile

2-(3-nitrophenyl)-2-((trimethylsilyl)oxy)propanenitrile

Conditions
ConditionsYield
With C29H46LaN3Si2 at 15℃; for 1h; Inert atmosphere; Glovebox; Schlenk technique;99%
N,N,N',N'-tetramethylguanidine at 25℃; for 15h;95%
With C48H40N8Sm(1-)*C16H32LiO4(1+) at 20℃; for 4h; Inert atmosphere; Schlenk technique;86%
With [η5:η1-(2,5-Me2C4H2N)CH2CH2]2NLa[N(SiMe3)2]2 In neat (no solvent) at 20℃; for 2h; Inert atmosphere; Schlenk technique;80%
With Li(2-(2,6-diisopropylphenylamino)-4-(2,6-diisopropylphenyl-imino)-2-pentene-H)(tetrahydtofuran) In tetrahydrofuran at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; Glovebox;98 %Spectr.
diethyl cyanophosphonate
2942-58-7

diethyl cyanophosphonate

lithium cyanide
2408-36-8

lithium cyanide

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

1-cyano-1-(3-nitrophenyl)ethyl diethyl phosphate
1469462-86-9

1-cyano-1-(3-nitrophenyl)ethyl diethyl phosphate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.0833333h;99%
acetonitrile
75-05-8

acetonitrile

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

β-acetamido-β-(3-methylphenyl)-3'-nitropropiophenone
1342806-10-3

β-acetamido-β-(3-methylphenyl)-3'-nitropropiophenone

Conditions
ConditionsYield
With acetyl chloride; trifluoroacetic acid at 0 - 33℃; for 5h; Dakin-West reaction;98.6%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

m-nitroacetophenone O-methyloxime

m-nitroacetophenone O-methyloxime

Conditions
ConditionsYield
With pyridine In methanol; toluene at 25℃; for 3h;98.5%
In ethanol; water at 20℃; for 4.75h; Heating / reflux;83.2%
With pyridine In ethanol at 60℃; for 6h;
With pyridine In ethanol at 60℃; for 6h;
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

4,3'-dinitro-trans-chalcone
131497-22-8

4,3'-dinitro-trans-chalcone

Conditions
ConditionsYield
With chloro-trimethyl-silane; palladium on activated charcoal In N,N-dimethyl-formamide at 75℃; for 5h;98%
With methanol; sodium methylate
1.2 gm (63%)
1.2 gm (63%)
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

3-(1-hydroxyethyl)aniline
2454-37-7

3-(1-hydroxyethyl)aniline

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 30℃; for 5h; chemoselective reaction;98%
With hydrogen In ethanol at 20℃; for 5h;98%
With sodium tetrahydroborate; antimony(III) fluoride In water; acetonitrile at 20℃; for 0.0833333h;95%
benzaldehyde
100-52-7

benzaldehyde

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

3'-nitro-chalcone
16619-21-9

3'-nitro-chalcone

Conditions
ConditionsYield
With sulfonated carbon In benzene Heating;98%
With sodium hydroxide In ethanol; water at 20℃; for 3h; Cooling with ice;94%
With sodium hydroxide In ethanol at 20℃; for 2h;92%
2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

3-(2,4-dichloro-phenyl)-3-hydroxy-1-(3-nitro-phenyl)-propan-1-one

3-(2,4-dichloro-phenyl)-3-hydroxy-1-(3-nitro-phenyl)-propan-1-one

Conditions
ConditionsYield
With sodium phosphate In methanol at 25 - 32℃; for 3.91667h; ultrasonic irradiation;98%
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

(E)-1-(3-nitrophenyl)ethan-1-one oxime
87974-55-8

(E)-1-(3-nitrophenyl)ethan-1-one oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 20℃; for 24h; pH=9; Cooling with ice;98%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 0 - 20℃; for 24h; pH=9;98%
Stage #1: 3-Nitroacetophenone With calcium oxide Heating;
Stage #2: With hydroxylamine hydrochloride
diethyl cyanophosphonate
2942-58-7

diethyl cyanophosphonate

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

1-cyano-1-(3-nitrophenyl)ethyl diethyl phosphate
1469462-86-9

1-cyano-1-(3-nitrophenyl)ethyl diethyl phosphate

Conditions
ConditionsYield
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In toluene at 20℃; for 4h; Inert atmosphere;98%
phenyl isocyanate
103-71-9

phenyl isocyanate

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

2-(1-(3-nitrophenyl)ethylidene)-N-phenylhydrazine-1-carboxamide

2-(1-(3-nitrophenyl)ethylidene)-N-phenylhydrazine-1-carboxamide

Conditions
ConditionsYield
Stage #1: 3-Nitroacetophenone With hydrazine hydrate In methanol for 0.5h;
Stage #2: phenyl isocyanate In methanol
98%
ethenetetracarbonitrile
670-54-2

ethenetetracarbonitrile

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

4-(3-nitrophenyl)-4-oxobutane-1,1,2,2-tetracarbonitrile

4-(3-nitrophenyl)-4-oxobutane-1,1,2,2-tetracarbonitrile

Conditions
ConditionsYield
With toluene-4-sulfonic acid In neat (no solvent) at 50 - 60℃; Green chemistry;98%
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

1,2-bis(1-(3-nitrophenyl)ethylidene)hydrazine
5340-12-5

1,2-bis(1-(3-nitrophenyl)ethylidene)hydrazine

Conditions
ConditionsYield
With carbazic acid at 60℃; for 24h; Neat (no solvent);97%
With ethanol; sodium carbonate; hydrazinium sulfate
With ethanol; hydrazine
With hydrazine hydrate; acetic acid In ethanol at 75℃;
With hydrazine hydrate; acetic acid In ethanol at 75℃;
3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

3'-nitro-2-bromoacetophenone
2227-64-7

3'-nitro-2-bromoacetophenone

Conditions
ConditionsYield
With aluminum (III) chloride; bromine In diethyl ether at 0 - 20℃; for 1h;97%
With aluminum (III) chloride; bromine In diethyl ether at 0 - 20℃; for 1h;97%
With aluminum (III) chloride; bromine In diethyl ether at 0 - 20℃; for 1h;97%
4-amino-1,2,4-triazole
584-13-4

4-amino-1,2,4-triazole

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

(E)-N-<1-(3-nitrophenyl)ethylidene>-4H-1,2,4-triazol-4-amine
117979-27-8

(E)-N-<1-(3-nitrophenyl)ethylidene>-4H-1,2,4-triazol-4-amine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 24h; Heating;97%
5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole
947-95-5

5-chloro-4-formyl-3-methyl-1-phenyl-1H-pyrazole

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

C19H14ClN3O3
1252881-71-2

C19H14ClN3O3

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 0 - 5℃;97%
4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

3-Nitroacetophenone
121-89-1

3-Nitroacetophenone

2,4-bis(3-nitrophenyl)-2,7,8-trimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine
1369787-55-2

2,4-bis(3-nitrophenyl)-2,7,8-trimethyl-2,3-dihydro-1H-benzo[b][1,4]diazepine

Conditions
ConditionsYield
With chitosan-supported Fe3O4 nanoparticle In ethanol at 20℃; for 1.5h; Green chemistry;97%

121-89-1Relevant articles and documents

Polyoxovanadate catalysts for oxidation of 1-phenyl ethanol: From the discrete [V4O12]4- and [V10O28]6- anions to the anionic [V6O17]:N4 n - Coordination polymer

Wang, Ke,Xu, Qiaofei,Ma, Pengtao,Zhang, Chao,Wang, Jingping,Niu, Jingyang

, p. 6273 - 6279 (2018)

Three polyoxovanadate-based hybrids {[Ru(phen)3]2[V4O12]}·13H2O (1), [Ru(phen)3]2[V10O28]·15H2O (2), and [Ru(phen)3]2[V6O17]Cl·11H2O (3) (phen = 1,10-phenanthroline) were prepared under hydrothermal conditions and characterized by electron paramagnetic resonance (EPR) spectroscopy, infrared spectroscopy (IR), powder X-ray diffraction (PXRD), thermogravimetric (TG) analysis, X-ray photoelectron spectroscopy (XPS), and single crystal X-ray diffraction analysis. Although the structures of both the cyclic vanadate [V4O12]4- and the [V10O28]6- anions are well-known, interestingly, a novel 1-dimensional (1-D) coordination polymer [V6O17]n4n- anion was constructed from tetranuclear [V4O12]4- and dinuclear [V2O7]4- building blocks, which were linked alternately through corner-shared oxygen atoms. Furthermore, the negative charges of polyoxovanadate [V4O12]4-, [V10O28]6- and [V6O17]4- anions were balanced by two [Ru(phen)3]2+/3+ complex cations. The catalytic properties of compounds 1-3 for the oxidation of 1-phenyl ethanol by tert-butyl hydroperoxide (TBHP) were investigated, and the results demonstrated that 1 and 3 exhibited excellent catalytic activities for the oxidation of 1-phenyl ethanol under mild catalytic conditions.

Nonselective bromination-selective debromination strategy: Selective bromination of unsymmetrical ketones on singly activated carbon against doubly activated carbon

Choi, Han Young,Chi, Dae Yoon

, p. 411 - 414 (2003)

(Matrix presented) We have found a new synthetic method for the preparation of the α-bromoketones that are brominated in the less activated terminal position of unsymmetrical ketones. Brominations in short reaction times (kinetically controlled) provided internally brominated compounds as a major product. However, brominations in longer reaction times (thermodynamically controlled) gave more of the terminally brominated compound through the reversible reaction by Br2 and produced hydrogen bromide. Several brominated compounds at the terminal position were successfully prepared through the new synthetic route.

Ortho Enhancement in the Ozone-Mediated Nitration of Some Aromatic Carbonyl Compounds with Nitrogen Dioxide

Suzuki, Hitomi,Murashima, Takashi,Tatsumi, Atsuo,Kozai, Iku

, p. 1421 - 1424 (1993)

Alkyl aryl ketones react smoothly with nitrogen dioxide at low temperatures in the presence of ozone to give a mixture of ortho and meta nitration products (o/m = 1.1-3.8/1.0), the former becoming predominant with the increasing size of alkyl moiety.

-

Barkenbus,Clements

, p. 1369 (1934)

-

A Stable Polyoxometalate-Based Metal-Organic Framework as Highly Efficient Heterogeneous Catalyst for Oxidation of Alcohols

Li, Dandan,Xu, Qiaofei,Li, Yingguang,Qiu, Yueting,Ma, Pengtao,Niu, Jingyang,Wang, Jingping

, p. 4945 - 4953 (2019)

A novel copper-containing 3D polyoxometalate-based metal-organic framework (POMOF), H[Cu5ICuII(pzc)2(pz)4.5{P2W18O62}]·6H2O (HENU-1, HENU = Henan University; Hpzc = pyrazine-2-carboxylic acid, pz = pyrazine), was successfully isolated by a one-step hydrothermal method. In this compound, the {P2W18} polyanion acts as a seven-connected linker bridging adjacent 2D double-layer networks, as well as a template to induce the formation of the desired 3D framework. Particularly, the pz ligands are generated from pzc ligands in situ during the reaction process. HENU-1 exhibits not only good stability in air but also tolerance to acidic and basic media. It was first employed as a highly efficient heterogeneous catalyst for the oxidation of 1-phenylethanol into acetophenone, which shows 97% yield using tert-butyl hydroperoxide as oxidant with a turnover frequency of up to 9690·h-1, and was reused for at least five cycles without significant catalytic activity loss. No POM leaching or framework decomposition was observed in our study.

Interfacially synthesized 2D COF thin film photocatalyst: efficient photocatalyst for solar formic acid production from CO2and fine chemical synthesis

Yadav, Dolly,Kumar, Abhishek,Kim, Jae Young,Park, No-Joong,Baeg, Jin-Ook

supporting information, p. 9573 - 9580 (2021/04/26)

The targeted synthesis of an efficient, visible light active, recyclable, freestanding covalent organic framework thin film photocatalyst for multi-faceted photocatalysis is the essence of the proposed work. A simple, scalable, reagent free synthesis of a thin film at the interface of 5,10,15,20-tetra-(4-aminophenyl)porphyrin, 2-vinylbenzene-1,4-dicarbaldehyde in nitrobenzene and aqueous glyoxal affords centimetre sized continuous 2D thin film with substantial stability, flexibility and efficient visible light activity. Strikingly different from the regular imine based COF, the incorporation of the glyoxal unit as a modulator helps in band gap tuning and induces flexibility within the thin film. An interplay between time and concentration helps in achieving a thin film photocatalyst with efficient photocatalytic activity for 1,4-NADH regeneration and selective formic acid formation from CO2. The optimum band edge position of the thin film photocatalyst also enables solar fine chemical synthesisviareductive dehalogenation under visible light illumination with excellent recyclability. The present work gives insight into visible light active thin film formation en route to metal-free sustainable photocatalysis.

g-C3N4/H3PW4Mo8O40 S-scheme photocatalyst with enhanced photocatalytic oxidation of alcohols and sulfides

Fazlali, Farnaz,Khazaee, Zeynab,Najminejad, Zohreh,Nejat, Razieh,Shahraki, Somaye

, (2021/08/16)

In this work, graphitic carbon nitride (g-C3N4) decorated with molybdenum-substituted tungstophosphoric acid as a novel photocatalyst (H3PW4Mo8O40/g-C3N4) was used to catalyze the oxidation of alcohols and sulfides. H3PW4Mo8O40/g-C3N4 (PW4Mo8/g-C3N4) displays higher photocatalytic activity under visible light irradiation for the oxidation of alcohols and sulfides compared with Keggin/g-C3N4 (PW12/g-C3N4). To obtain the optimum value, molybdenum substitution contents (H3PW12-xMoxO40) were changed from x = 4 to 12. The results showed that PW4Mo8 produces the best yield under visible-light irradiation. The results showed that PW4Mo8 was the best sample. The reaction rate increase can be due to the redox and acid properties of PW4Mo8/g-C3N4. This study provides a new insight for the preparation of highly efficient photocatalysts for the oxidation of organic compounds.

Ru(iii) -based polyoxometalate tetramers as highly efficient heterogeneous catalysts for alcohol oxidation reactions at room temperature

Li, Huafeng,Ma, Pengtao,Niu, Jingyang,Song, Junpeng,Wang, Jingping,Wang, Yaqiong,Zhao, Xue,Zou, Yan

, p. 12664 - 12673 (2021/09/28)

A novel ruthenium-containing polyoxometalate-based organic-inorganic hybrid, K4Na9H7.4[(AsW9O33)4(WO2)4{Ru3.2(C3H3N2)2}]·42H2O (1), was successfully synthesized by a one-step hydrothermal method under acidic conditions, which applied a self-assembly strategy between inorganic polyoxometalate based on trivacant [B-α-AsW9O33]9?{AsW9} fragments and an organic ligand, imidazole (C3H4N2). Compound1was further characterized by single-crystal X-ray diffraction, PXRD, IR spectroscopy, UV-Vis spectroscopy, ESI-MS, elemental analysis and TGA. Single-crystal X-ray diffraction data reveal that the polyanion consists of four trivacant Keggin-type polyanion {AsW9} building blocks bridged by four {WO6} units, leading to a crown-shaped tetrameric structure [(AsW9O33)4(WO2)4{Ru3.2(C3H3N2)2}]20.4?. The ESI-MS result reveals that the polyanion unit has excellent structural integrity in water. Moreover, the catalysis study of1was also further investigated, and the experimental results indicate heterogeneous catalyst1presents high efficiency (yield = 98%), excellent selectivity (>99%), and good recyclability for the oxidation of 1-(4-chlorophenyl)ethanol to 4′-chloroacetophenone with commercially available 70% aqueoustert-butyl hydroperoxide {TBHP (aq.)} as the oxidant at room temperature.

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