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15128-82-2

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15128-82-2 Usage

Chemical Properties

yellow crystalline powder

Uses

3-Hydroxy-2-nitropyridine may be used in the synthesis of novel sulfonates that are potent inhibitors of cell proliferation and tubulin polymerization.

Preparation

Synthesis of 3-hydroxy-2-nitropyridine: add 10g of 3-hydroxypyridine, 80ml of ethyl acetate, 4.2g of KNO3 and 21ml of acetic anhydride into a 250mL three-necked flask, and heat at 45°C with magnetic stirring After the reaction is completed, it is cooled to room temperature, filtered with suction, washed with a small amount of ethyl acetate for 1 to 2 times, the filtrate is taken to adjust the pH to neutrality with saturated NaOH solution, and extracted with ethyl acetate for 3 to 4 times. , take the extract and add activated carbon and heat under reflux for 1 hour, cool and filter, take the filtrate, dry with anhydrous magnesium sulfate, filter, concentrate on a rotary evaporator, and dry in a drying oven. 11.9 g of 3-hydroxy-2-nitropyridine was obtained with a yield of 81%.

Check Digit Verification of cas no

The CAS Registry Mumber 15128-82-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,1,2 and 8 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 15128-82:
(7*1)+(6*5)+(5*1)+(4*2)+(3*8)+(2*8)+(1*2)=92
92 % 10 = 2
So 15128-82-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H4N2O3/c8-4-2-1-3-6-5(4)7(9)10/h1-3,8H

15128-82-2 Well-known Company Product Price

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  • Detail
  • Alfa Aesar

  • (A14887)  3-Hydroxy-2-nitropyridine, 98%   

  • 15128-82-2

  • 10g

  • 590.0CNY

  • Detail
  • Alfa Aesar

  • (A14887)  3-Hydroxy-2-nitropyridine, 98%   

  • 15128-82-2

  • 50g

  • 1389.0CNY

  • Detail
  • Alfa Aesar

  • (A14887)  3-Hydroxy-2-nitropyridine, 98%   

  • 15128-82-2

  • 100g

  • 1447.0CNY

  • Detail
  • Alfa Aesar

  • (A14887)  3-Hydroxy-2-nitropyridine, 98%   

  • 15128-82-2

  • 250g

  • 3074.0CNY

  • Detail
  • Aldrich

  • (107255)  3-Hydroxy-2-nitropyridine  97%

  • 15128-82-2

  • 107255-25G

  • 657.07CNY

  • Detail
  • Aldrich

  • (107255)  3-Hydroxy-2-nitropyridine  97%

  • 15128-82-2

  • 107255-100G

  • 3,011.58CNY

  • Detail

15128-82-2SDS

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-Hydroxy-2-nitropyridine

1.2 Other means of identification

Product number -
Other names 3-Hydroxy-2-Nitropyrine

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:15128-82-2 SDS

15128-82-2Synthetic route

3-ethoxy-2-nitropyridine
74037-50-6

3-ethoxy-2-nitropyridine

3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; water at 90℃; for 12h;69%
3-HYDROXYPYRIDINE
109-00-2

3-HYDROXYPYRIDINE

3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

Conditions
ConditionsYield
With aluminium trinitrate In acetonitrile at 50℃; regioselective reaction;60%
With sulfuric acid; nitric acid at 20 - 30℃;
With sulfuric acid; nitric acid at 35 - 50℃;
3-hydroxypyridine nitrate

3-hydroxypyridine nitrate

3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

Conditions
ConditionsYield
With sulfuric acid at 50℃;
With sulfuric acid at 50℃;
3-HYDROXYPYRIDINE
109-00-2

3-HYDROXYPYRIDINE

nitric acid (D:1.52)

nitric acid (D:1.52)

sulfuric acid (D:1.84)

sulfuric acid (D:1.84)

3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

1-(2,6-dichloro-3-fluorophenyl)ethanol
756520-66-8

1-(2,6-dichloro-3-fluorophenyl)ethanol

(±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine
756521-08-1

(±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4h; Inert atmosphere;100%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 4h;98%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 4h;98%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

ethyl iodide
75-03-6

ethyl iodide

3-ethoxy-2-nitropyridine
74037-50-6

3-ethoxy-2-nitropyridine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;100%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

ethyl bromoacetate
105-36-2

ethyl bromoacetate

C9H10N2O5

C9H10N2O5

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h;
Stage #2: ethyl bromoacetate In N,N-dimethyl-formamide
100%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

C10H12N2O5

C10H12N2O5

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h;
Stage #2: Ethyl 2-bromopropionate In N,N-dimethyl-formamide
100%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

2-bromobutyric acid ethyl ester
533-68-6

2-bromobutyric acid ethyl ester

C11H14N2O5

C11H14N2O5

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h;
Stage #2: 2-bromobutyric acid ethyl ester In N,N-dimethyl-formamide
100%
2-bromo-pentanoic acid ethyl ester
615-83-8

2-bromo-pentanoic acid ethyl ester

3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

C12H16N2O5

C12H16N2O5

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h;
Stage #2: 2-bromo-pentanoic acid ethyl ester In N,N-dimethyl-formamide
100%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

Ethyl 2-bromohexanoate
615-96-3

Ethyl 2-bromohexanoate

C13H18N2O5

C13H18N2O5

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine With potassium hydroxide In ethanol for 1h;
Stage #2: Ethyl 2-bromohexanoate In N,N-dimethyl-formamide
100%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

diethyl 2-[(2-nitro-3-pyridyl)oxy]malonate
499787-33-6

diethyl 2-[(2-nitro-3-pyridyl)oxy]malonate

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine With potassium fluoride In N,N-dimethyl-formamide at 0℃; for 0.5h; Kikelj reaction;
Stage #2: Diethyl 2-bromomalonate In N,N-dimethyl-formamide at 20℃; for 24h;
99%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

4,4,4-trifluorobutanol
461-18-7

4,4,4-trifluorobutanol

2-nitro-3-(4,4,4-trifluorobutoxy)pyridine

2-nitro-3-(4,4,4-trifluorobutoxy)pyridine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2.5h; Mitsunobu Displacement;99%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

1-(2,6-dichloro-3-fluorophenyl)ethanol
756520-66-8

1-(2,6-dichloro-3-fluorophenyl)ethanol

3-[(2,6-dichloro-3-fluorophenyl)methoxy]-2-nitropyridine
941602-99-9

3-[(2,6-dichloro-3-fluorophenyl)methoxy]-2-nitropyridine

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 4h;98%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 4h; Inert atmosphere;98%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

6-bromo-2-nitropyridin-3-ol
443956-08-9

6-bromo-2-nitropyridin-3-ol

Conditions
ConditionsYield
With bromine; sodium methylate In methanol at 0 - 20℃; for 1h;96%
Stage #1: 3-hydroxy-2-nitropyridine With sodium methylate In methanol at 20℃; for 0.5h;
Stage #2: With bromine In methanol at 0℃; for 0.5h;
Stage #3: With acetic acid In methanol
96%
Stage #1: 3-hydroxy-2-nitropyridine With sodium methylate In methanol at 20℃; for 0.5h;
Stage #2: With bromine In methanol at 0℃; for 0.5h;
Stage #3: With acetic acid In methanol
96%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

2-nitro-3-(trifluoromethylsulfonyloxy)pyridine
146336-72-3

2-nitro-3-(trifluoromethylsulfonyloxy)pyridine

Conditions
ConditionsYield
With triethylamine In dichloromethane for 2h;95%
With triethylamine In dichloromethane for 2h; Cooling with ice;95%
With triethylamine In dichloromethane for 2h; Cooling with ice;95%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

4-methoxy-phenyl-sulphonyl chloride
98-68-0

4-methoxy-phenyl-sulphonyl chloride

4-methoxy-benzenesulfonic acid 2-nitro-pyridin-3-yl ester
360061-93-4

4-methoxy-benzenesulfonic acid 2-nitro-pyridin-3-yl ester

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane95%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

(R)-1-(2,6-dichloro-3-fluorophenyl)-1-ethanol
330156-50-8

(R)-1-(2,6-dichloro-3-fluorophenyl)-1-ethanol

(S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

(S)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-nitropyridine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;95%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 4h; Inert atmosphere;95%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20 - 30℃; Cooling with ice;80%
Stage #1: 3-hydroxy-2-nitropyridine; (R)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol With triphenylphosphine In tetrahydrofuran at 20℃; for 1h;
Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 30℃;
80%
Stage #1: 3-hydroxy-2-nitropyridine; (R)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol With triphenylphosphine In toluene at 10℃; for 0.166667h;
Stage #2: With di-isopropyl azodicarboxylate In toluene at 8 - 25℃; for 5h;
68.8 g
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

N,N-Dimethylthiocarbamoyl chloride
16420-13-6

N,N-Dimethylthiocarbamoyl chloride

N,N-dimethyl-1-[(2-nitropyridin-3-yl)oxy]methanethioamide
152170-26-8

N,N-dimethyl-1-[(2-nitropyridin-3-yl)oxy]methanethioamide

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide for 24h;93%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h;69%
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 24h;
With 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 20℃; for 24h;
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

C9H9Cl2FO3S
877399-98-9

C9H9Cl2FO3S

(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine
877397-70-1

(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 2-methyltetrahydrofuran for 4h; Reagent/catalyst; Solvent; Temperature; Reflux;92.1%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

(S)-Ethyl lactate
687-47-8

(S)-Ethyl lactate

ethyl (2R)-2-[(2-nitropyridin-3-yl)oxy]propanoate

ethyl (2R)-2-[(2-nitropyridin-3-yl)oxy]propanoate

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine; (S)-Ethyl lactate With triphenylphosphine In dichloromethane at 20℃; for 0.3h;
Stage #2: With di-isopropyl azodicarboxylate In dichloromethane at 20℃; for 16h;
92%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

8-azido-3,6-dioxaoctyl tosylate
178685-33-1

8-azido-3,6-dioxaoctyl tosylate

3‐(2‐(2‐(2‐azidoethoxy)ethoxy)ethoxy)‐2‐nitropyridine

3‐(2‐(2‐(2‐azidoethoxy)ethoxy)ethoxy)‐2‐nitropyridine

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: 8-azido-3,6-dioxaoctyl tosylate In N,N-dimethyl-formamide at 90℃; for 48h;
92%
ethyl 2-bromoisobutyrate
600-00-0

ethyl 2-bromoisobutyrate

3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

2-methyl-2-((2-nitropyridin-3-yl)oxy)propanoic acid ethyl ester

2-methyl-2-((2-nitropyridin-3-yl)oxy)propanoic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 24h; Reagent/catalyst; Solvent; Temperature;91.57%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

methyl iodide
74-88-4

methyl iodide

3-methoxy-2-nitropyridine
20265-37-6

3-methoxy-2-nitropyridine

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide for 0.333333h;90.9%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

(2,6-dichloro-3-fluorophenyl)methanol
1227611-90-6

(2,6-dichloro-3-fluorophenyl)methanol

3-[(2,6-dichloro-3-fluorophenyl)methoxy]-2-nitropyridine
941602-99-9

3-[(2,6-dichloro-3-fluorophenyl)methoxy]-2-nitropyridine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0℃; for 16h; Mitsunobu Displacement; Inert atmosphere;90%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

(S)‐1‐(2,6-dichloro-3-fluorophenyl)ethanol
877397-65-4

(S)‐1‐(2,6-dichloro-3-fluorophenyl)ethanol

(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine
877397-70-1

(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 13h;88.3%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 13h;88.3%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;88%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

(R)-1-(2,6-dichloro-3-fluorophenyl)-1-ethanol
330156-50-8

(R)-1-(2,6-dichloro-3-fluorophenyl)-1-ethanol

(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine
877397-70-1

(R)-3-(1-(2,6-dichloro-3-fluorophenyl)ethyoxyl)-2-nitropyridine

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine; (R)-1-(2,6-dichloro-3-fluorophenyl)ethan-1-ol With triphenylphosphine In tetrahydrofuran at 20℃; for 1h;
Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 0℃; for 12h;
88.3%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

2,4-Dichlorobenzyl chloride
94-99-5

2,4-Dichlorobenzyl chloride

3-((2,4-dichlorobenzyl)oxy)-2-nitropyridine
756480-74-7

3-((2,4-dichlorobenzyl)oxy)-2-nitropyridine

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 90℃; for 2h; Inert atmosphere;88%
With caesium carbonate In acetonitrile at 90℃; for 2h;88%
2-bromo-2-methylpropionic acid methyl ester
23426-63-3

2-bromo-2-methylpropionic acid methyl ester

3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

methyl 2-methyl-2-[(2-nitropyridin-3-yl)oxy]propanoate
1373771-93-7

methyl 2-methyl-2-[(2-nitropyridin-3-yl)oxy]propanoate

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide87%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

(S)-1-(5-fluoro-2-methoxyphenyl)ethanol

(S)-1-(5-fluoro-2-methoxyphenyl)ethanol

A

3-[(S)-1-(5-fluoro-2-methoxyphenyl)ethoxy]-2-nitropyridine

3-[(S)-1-(5-fluoro-2-methoxyphenyl)ethoxy]-2-nitropyridine

B

3-[(R)-1-(5-fluoro-2-methoxyphenyl)ethoxy]-2-nitropyridine
1346817-64-8

3-[(R)-1-(5-fluoro-2-methoxyphenyl)ethoxy]-2-nitropyridine

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 0 - 20℃;A n/a
B 86%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

2-nitro-3-(1-(pyridin-2-yl)ethoxy)pyridine

2-nitro-3-(1-(pyridin-2-yl)ethoxy)pyridine

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;85%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

C12H16FNO2

C12H16FNO2

C17H18FN3O4

C17H18FN3O4

Conditions
ConditionsYield
Stage #1: 3-hydroxy-2-nitropyridine; C12H16FNO2 With di-isopropyl azodicarboxylate; triphenylphosphine In toluene at 20℃; Inert atmosphere;
Stage #2: With zinc(II) chloride In ethanol at 20℃; for 5h; Solvent;
85%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

methyl (3,4,5-tri-O-acetyl-β-D-arabino-hex-2-ulopyranosyl)onate bromide
225937-33-7

methyl (3,4,5-tri-O-acetyl-β-D-arabino-hex-2-ulopyranosyl)onate bromide

(2S,3S,4R,5R)-3,4,5-Triacetoxy-2-(2-nitro-pyridin-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4R,5R)-3,4,5-Triacetoxy-2-(2-nitro-pyridin-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In acetone Heating;82%
3-hydroxy-2-nitropyridine
15128-82-2

3-hydroxy-2-nitropyridine

epichlorohydrin
106-89-8

epichlorohydrin

2-nitro-3-oxiranylmethoxypyridine
54127-40-1

2-nitro-3-oxiranylmethoxypyridine

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 72h;81%
With potassium carbonate In acetonitrile

15128-82-2Relevant articles and documents

Iodine(III)-Catalyzed Electrophilic Nitration of Phenols via Non-Br?nsted Acidic NO2+ Generation

Juárez-Ornelas, Kevin A.,Jiménez-Halla, J. Oscar C.,Kato, Terumasa,Solorio-Alvarado, César R.,Maruoka, Keiji

supporting information, p. 1315 - 1319 (2019/03/07)

The first catalytic procedure for the electrophilic nitration of phenols was developed using iodosylbenzene as an organocatalyst based on iodine(III) and aluminum nitrate as a nitro group source. This atom-economic protocol occurs under mild, non-Br?nsted acidic and open-flask reaction conditions with a broad functional-group tolerance including several heterocycles. Density functional theory (DFT) calculations at the (SMD:MeCN)Mo8-HX/(LANLo8+f,6-311+G) level indicated that the reaction proceeds through a cationic pathway that efficiently generates the NO2+ ion, which is the nitrating species under neutral conditions.

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