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13161-30-3

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13161-30-3 Usage

Description

2-Pyridinol-1-oxide (HOPO) is a versatile organic compound that serves as a peptide coupling agent and can form stable chelate complexes with transition metal ions. It is related to aspergillic acid and is derived from pyridine-N-oxide. With its bactericidal properties and ability to create chelates, 2-Pyridinol-1-oxide has found applications in various fields.

Uses

Used in Electrochemistry:
2-Pyridinol-1-oxide is used as a component in the fabrication of gold electrodes for the electrochemical determination of europium using cyclic voltammetry. Its ability to form stable chelates with metal ions makes it suitable for enhancing the selectivity and sensitivity of the electrochemical detection process.
Used in Polymer Chemistry:
In the field of polymer chemistry, 2-Pyridinol-1-oxide is used in the preparation of polymeric nickel (II) complexes of 2-hydroxypyridine-N-oxide. These complexes exhibit unique properties and can be utilized in various applications, such as catalysis and material science.
Used in Organic Synthesis:
2-Pyridinol-1-oxide plays a crucial role in the synthesis of 1-methoxypyrid-4-one, a key intermediate in the production of various pharmaceuticals and agrochemicals. The synthesis process involves the use of sodium methoxide and methyl toluene-9-sulphonate, highlighting the compound's reactivity and utility in organic synthesis.
Used as a Peptide Coupling Agent:
As a substitute for HOBt, 2-Pyridinol-1-oxide (HOPO) is used as a peptide coupling agent in the synthesis of peptides and proteins. Its ability to form stable chelates with transition metal ions aids in the efficient formation of peptide bonds, making it a valuable tool in the field of biochemistry and pharmaceutical development.
Used in Bactericidal Applications:
2-Pyridinol-1-oxide is also employed as a bactericidal agent due to its relationship with aspergillic acid. This property makes it useful in various applications, such as disinfectants, sanitizers, and preservatives, where controlling bacterial growth is essential.

Check Digit Verification of cas no

The CAS Registry Mumber 13161-30-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,6 and 1 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 13161-30:
(7*1)+(6*3)+(5*1)+(4*6)+(3*1)+(2*3)+(1*0)=63
63 % 10 = 3
So 13161-30-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H5NO2/c7-5-3-1-2-4-6(5)8/h1-4,7H

13161-30-3 Well-known Company Product Price

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  • TCI America

  • (H0672)  2-Hydroxypyridine N-Oxide  >98.0%(T)

  • 13161-30-3

  • 25g

  • 670.00CNY

  • Detail
  • Alfa Aesar

  • (H54207)  2-Hydroxypyridine N-oxide, 98+%   

  • 13161-30-3

  • 5g

  • 190.0CNY

  • Detail
  • Alfa Aesar

  • (H54207)  2-Hydroxypyridine N-oxide, 98+%   

  • 13161-30-3

  • 25g

  • 760.0CNY

  • Detail
  • Alfa Aesar

  • (H54207)  2-Hydroxypyridine N-oxide, 98+%   

  • 13161-30-3

  • 100g

  • 2527.0CNY

  • Detail
  • Aldrich

  • (56413)  2-Pyridinol1-oxide  ≥98.0% (N)

  • 13161-30-3

  • 56413-25G

  • 1,347.84CNY

  • Detail
  • Aldrich

  • (56413)  2-Pyridinol1-oxide  ≥98.0% (N)

  • 13161-30-3

  • 56413-100G

  • 4,266.99CNY

  • Detail

13161-30-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Pyridinol-1-oxide

1.2 Other means of identification

Product number -
Other names 2-Hydroxypyridine n-oxide

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:13161-30-3 SDS

13161-30-3Synthetic route

2-hydroxypyridin
142-08-5

2-hydroxypyridin

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With titanium silicate; dihydrogen peroxide In methanol at 60℃; for 25h; Oxidation;92%
With oxygen; ruthenium trichloride In 1,2-dichloro-ethane at 20℃; under 760 Torr; for 12h;52%
With Perbenzoic acid In 1,4-dioxane; water at 20℃; Thermodynamic data; Kinetics; Mechanism; other temp. (25, 30, 35 deg C); ΔS(excit.);
2,2-dimethyl-4-(2-oxo-1H-pyrid-1-yl)oxy-2H-1,3-benzoxazine
74405-16-6

2,2-dimethyl-4-(2-oxo-1H-pyrid-1-yl)oxy-2H-1,3-benzoxazine

A

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

B

salicylamide

salicylamide

Conditions
ConditionsYield
With hydrogenchloride for 3h; Product distribution; Ambient temperature;A 90%
B n/a
N-oxy-2-pyridyl phenacyl sulfoxide
65332-95-8

N-oxy-2-pyridyl phenacyl sulfoxide

2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

A

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

B

2-Benzoyl-3,6-dihydro-4,5-dimethyl-2H-thiopyran
80738-10-9

2-Benzoyl-3,6-dihydro-4,5-dimethyl-2H-thiopyran

Conditions
ConditionsYield
In 1,4-dioxane at 100℃; for 24h; Yields of byproduct given;A n/a
B 85%
2-methoxypyridine N-oxide
20773-98-2

2-methoxypyridine N-oxide

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With hydrogenchloride; water at 90 - 100℃; for 16h;54%
With hydrogenchloride Heating;
pyridine N-oxide
694-59-7

pyridine N-oxide

A

3-hydroxypyridine N-oxide
6602-28-4

3-hydroxypyridine N-oxide

B

4-hydroxypyridine N-oxide
6890-62-6

4-hydroxypyridine N-oxide

C

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With water; hexachloroiridate(IV); dinitrogen monoxide Rate constant; Irradiation;
N-oxy-2-pyridyl phenacyl sulfoxide
65332-95-8

N-oxy-2-pyridyl phenacyl sulfoxide

A

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

B

2-Benzoyl-3,6-dihydro-4,5-dimethyl-2H-thiopyran
80738-10-9

2-Benzoyl-3,6-dihydro-4,5-dimethyl-2H-thiopyran

Conditions
ConditionsYield
With 2,3-dimethyl-buta-1,3-diene In 1,4-dioxane at 100℃; for 24h; Title compound not separated from byproducts;A 98 % Spectr.
B 99 % Spectr.
2-methoxypyridine
1628-89-3

2-methoxypyridine

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AcOH; H2O2
2: aq. HCl / Heating
View Scheme
2-chloropyridine
109-09-1

2-chloropyridine

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 60 percent / MCPBA / CHCl3 / 24 h / 65 - 70 °C
2: 50 percent / NaOMe / 1 h / Heating
3: 54 percent / HCl, H2O / 16 h / 90 - 100 °C
View Scheme
2-chloropyridine-N-oxide
2402-95-1

2-chloropyridine-N-oxide

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / NaOMe / 1 h / Heating
2: 54 percent / HCl, H2O / 16 h / 90 - 100 °C
View Scheme
2-oxopyridin-1(2H)-yl 4-nitrobenzenesulfonate
1259401-62-1

2-oxopyridin-1(2H)-yl 4-nitrobenzenesulfonate

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In N-(2-hydroxyethyl)piperazine-N-(2-hydroxyethyl)piperazine-N'-ethanesulfonic acid pH=7.5;
2-oxopyridin-1(2H)-yl 2,4-dinitrobenzenesulfonate
1259401-63-2

2-oxopyridin-1(2H)-yl 2,4-dinitrobenzenesulfonate

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In N-(2-hydroxyethyl)piperazine-N-(2-hydroxyethyl)piperazine-N'-ethanesulfonic acid pH=7.5;
4-(((2-oxopyridin-1(2H)-yl)oxy)sulfonyl)benzoic acid
1259401-64-3

4-(((2-oxopyridin-1(2H)-yl)oxy)sulfonyl)benzoic acid

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In N-(2-hydroxyethyl)piperazine-N-(2-hydroxyethyl)piperazine-N'-ethanesulfonic acid pH=7.5; Kinetics;
With dihydrogen peroxide at 20℃; pH=7.5; Kinetics; HEPES buffer;
2-oxopyridin-1(2H)-yl benzenesulfonate
5033-19-2

2-oxopyridin-1(2H)-yl benzenesulfonate

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In N-(2-hydroxyethyl)piperazine-N-(2-hydroxyethyl)piperazine-N'-ethanesulfonic acid pH=7.5; Kinetics;
With dihydrogen peroxide at 20℃; pH=7.5; Kinetics; HEPES buffer;
2-oxopyridin-1(2H)-yl 4-methylbenzene sulfonate
5087-06-9

2-oxopyridin-1(2H)-yl 4-methylbenzene sulfonate

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In N-(2-hydroxyethyl)piperazine-N-(2-hydroxyethyl)piperazine-N'-ethanesulfonic acid pH=7.5; Kinetics;
With dihydrogen peroxide at 20℃; pH=7.5; Kinetics; HEPES buffer;
4-(((2-oxopyridin-1(2H)-yl)oxy)methyl)phenylboronic acid
1325206-84-5

4-(((2-oxopyridin-1(2H)-yl)oxy)methyl)phenylboronic acid

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; pH=7.5; Kinetics; HEPES buffer;
1-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)pyridin-2(1H)-one
1254765-78-0

1-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)pyridin-2(1H)-one

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide at 20℃; pH=7.5; Kinetics; HEPES buffer;
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

2-hydroxypyridin
142-08-5

2-hydroxypyridin

Conditions
ConditionsYield
With triphenylphosphine; N-fused tetraphenylporphyrin rhenium(VII) trioxide In dichloromethane at 23℃; for 3h;99%
With carbon dioxide; water; iron at 100℃; for 10h; Autoclave; Green chemistry; chemoselective reaction;99%
With ammonium formate; silica gel; zinc In methanol at 20℃; for 0.166667h; chemoselective reaction;91%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

5-aminopentanal hydrochloride

5-aminopentanal hydrochloride

Conditions
ConditionsYield
Stage #1: 2-hydroxy-pyridine N-oxide With ammonium formate; 10percent palladium on carbon In methanol Heating;
Stage #2: With hydrogenchloride In methanol Further stages.;
98%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

ammonium tetraphenylborate
14637-34-4

ammonium tetraphenylborate

2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan

2,2-diphenyl-1,3-dioxa-3a-azonia-2-borataindan

Conditions
ConditionsYield
In toluene byproducts: NH3, C6H6; soln. of B compd. and ligand refluxed for 15 h; filtered, filtrate evapd. to dryness, recrystd. from EtOH; elem. anal.;93%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

2-oxopyridin-1(2H)-yl 4-nitrobenzenesulfonate
1259401-62-1

2-oxopyridin-1(2H)-yl 4-nitrobenzenesulfonate

Conditions
ConditionsYield
With pyridine at 20℃; Inert atmosphere;92%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

1,1'-carbonyldioxydi[2(1H)-pyridone]

1,1'-carbonyldioxydi[2(1H)-pyridone]

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 24h;91%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

gallium(III) nitrate hydrate

gallium(III) nitrate hydrate

Ga(3+)*3C5H4NO2(1-)

Ga(3+)*3C5H4NO2(1-)

Conditions
ConditionsYield
With sodium hydroxide In water pH=7;90%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

4,7-Dichloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine
81415-92-1

4,7-Dichloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine

1-(7-Chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazin-4-yloxy)-1H-pyridin-2-one
81416-09-3

1-(7-Chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazin-4-yloxy)-1H-pyridin-2-one

Conditions
ConditionsYield
With triethylamine In chloroform Heating;89%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

2-oxopyridin-1(2H)-yl 4-methylbenzene sulfonate
5087-06-9

2-oxopyridin-1(2H)-yl 4-methylbenzene sulfonate

Conditions
ConditionsYield
With pyridine at 20℃; Inert atmosphere;89%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

ammonium vanadate(V)

ammonium vanadate(V)

water
7732-18-5

water

NH4[VO2(2-hydroxypyridine-N-oxide(-1H))2]*3H2O

NH4[VO2(2-hydroxypyridine-N-oxide(-1H))2]*3H2O

Conditions
ConditionsYield
With acetic acid In ammonia; water aq. NH3; Sonication; aq. 25% NH3 soln. and H2O added to NH4VO3 and solid ligand; sonicated and heated gently; pH adjusted to 6.9-7.0 (aq. acetic acid); heated to boiling; cooled to room temp.; crystd. for 12 h; crystals collected; additional crystals obtained by slow evapn. of solvent; elem. anal.;88.7%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

4-Chloro-2,2-diethyl-2H-benzo[e][1,3]oxazine
74405-11-1

4-Chloro-2,2-diethyl-2H-benzo[e][1,3]oxazine

1-(2,2-Diethyl-2H-benzo[e][1,3]oxazin-4-yloxy)-1H-pyridin-2-one
81416-05-9

1-(2,2-Diethyl-2H-benzo[e][1,3]oxazin-4-yloxy)-1H-pyridin-2-one

Conditions
ConditionsYield
With triethylamine In chloroform Heating;88%
potassium hydridotris(3-phenylpyrazol-1-yl)borate

potassium hydridotris(3-phenylpyrazol-1-yl)borate

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

copper(II) choride dihydrate

copper(II) choride dihydrate

[Cu2(μ-Cl)2(2-hydroxypyridine-N-oxide(-H))2(3-phenylpyrazolyl)2]

[Cu2(μ-Cl)2(2-hydroxypyridine-N-oxide(-H))2(3-phenylpyrazolyl)2]

Conditions
ConditionsYield
In dichloromethane soln. of 2-OH-pyridine N-oxide (0.104 mmol) in CH2Cl2 added dropwise to soln. of borate (0.104 mmol) and Cu salt (0.104 mmol) in CH2Cl2 under stirring, mixt. stirred at room temp. for 16 h; ppt. removed by filtration, filtrate evapd. under vac., residue dissolved in CH2Cl2, recrystd. by diffusion of heptane into soln.; elem. anal.;87%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

4-bromomethylphenylboronic acid pinacol ester
138500-85-3

4-bromomethylphenylboronic acid pinacol ester

1-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)pyridin-2(1H)-one
1254765-78-0

1-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)pyridin-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;87%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine
74405-07-5

4-chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine

2,2-dimethyl-4-(2-oxo-1H-pyrid-1-yl)oxy-2H-1,3-benzoxazine
74405-16-6

2,2-dimethyl-4-(2-oxo-1H-pyrid-1-yl)oxy-2H-1,3-benzoxazine

Conditions
ConditionsYield
With triethylamine In chloroform Product distribution; Heating; reactions of several derivatives with var. pyridine N-oxides;85%
With triethylamine In chloroform Heating;85%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

2,2-dimethyl-4-chloro-6-methoxy-2H-1,3-benzoxazine
74405-14-4

2,2-dimethyl-4-chloro-6-methoxy-2H-1,3-benzoxazine

1-(6-Methoxy-2,2-dimethyl-2H-benzo[e][1,3]oxazin-4-yloxy)-1H-pyridin-2-one
81416-08-2

1-(6-Methoxy-2,2-dimethyl-2H-benzo[e][1,3]oxazin-4-yloxy)-1H-pyridin-2-one

Conditions
ConditionsYield
With triethylamine In chloroform Heating;85%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

benzyl bromide
100-39-0

benzyl bromide

1-(benzyloxy)pyridin-2(1H)-one
5280-02-4

1-(benzyloxy)pyridin-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;84%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

Ni(2+)*2C5H4NO2(1-)

Ni(2+)*2C5H4NO2(1-)

Conditions
ConditionsYield
In ethanol at 20℃; for 72h; Heating;83%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

2-anthroic acid
613-08-1

2-anthroic acid

1-(2-anthroyloxy)-2-pyridone
487010-91-3

1-(2-anthroyloxy)-2-pyridone

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane82%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

C13H14ClNO
74405-12-2

C13H14ClNO

C18H18N2O3
81416-06-0

C18H18N2O3

Conditions
ConditionsYield
With triethylamine In chloroform Heating;81%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

4,6-Dichloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine
74405-13-3

4,6-Dichloro-2,2-dimethyl-2H-benzo[e][1,3]oxazine

1-(6-Chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazin-4-yloxy)-1H-pyridin-2-one
81416-07-1

1-(6-Chloro-2,2-dimethyl-2H-benzo[e][1,3]oxazin-4-yloxy)-1H-pyridin-2-one

Conditions
ConditionsYield
With triethylamine In chloroform Heating;80%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

anthracene-1-carboxylic acid
607-42-1

anthracene-1-carboxylic acid

1-(1-anthroyloxy)-2-pyridone
487010-81-1

1-(1-anthroyloxy)-2-pyridone

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane78%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

[(9aneS3)Ru(dmso)3](PF6)2

[(9aneS3)Ru(dmso)3](PF6)2

C13H22NO3RuS4(1+)*F6P(1-)

C13H22NO3RuS4(1+)*F6P(1-)

Conditions
ConditionsYield
With sodium methylate In methanol for 2h; Reflux;78%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

2-oxopyridin-1(2H)-yl benzenesulfonate
5033-19-2

2-oxopyridin-1(2H)-yl benzenesulfonate

Conditions
ConditionsYield
With pyridine at 20℃; Inert atmosphere;77%
With pyridine at 20℃; Cooling with ice; Inert atmosphere;77%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

9-Anthracenecarboxylic acid
723-62-6

9-Anthracenecarboxylic acid

1-(9-anthroyloxy)-2-pyridone

1-(9-anthroyloxy)-2-pyridone

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane72%
zinc(II) sulfate heptahydrate

zinc(II) sulfate heptahydrate

2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

di(2-hydroxypyridine-N-oxidato)zinc(II)

di(2-hydroxypyridine-N-oxidato)zinc(II)

Conditions
ConditionsYield
With Ba(OH)2*8H2O In water byproducts: BaSO4; to an aq. soln. of 2-hydroxypyridine-N-oxide and Ba(OH)2*8H2O an aq. soln. of ZnSO4*7H2O added followed by stirring for 5 h at room temp.; filtration of BaSO4, removal of solvent, residue dissolved with hot water and reprecipitated with methanol, washed with a small amts. of methanol, elem. anal.;71%
With barium hydroxide octahydrate In water at 20℃;
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

A

3-amino-6-hydroxy pyridine N-oxide
900139-09-5

3-amino-6-hydroxy pyridine N-oxide

B

5-nitro-2-hydroxypyridine-N-oxide
14396-03-3

5-nitro-2-hydroxypyridine-N-oxide

Conditions
ConditionsYield
With nitric acid In acetic acidA n/a
B 68%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

5-nitro-2-hydroxypyridine-N-oxide
14396-03-3

5-nitro-2-hydroxypyridine-N-oxide

Conditions
ConditionsYield
With nitric acid; acetic acid In water at 10 - 35℃; for 0.5h;68%
2-hydroxy-pyridine N-oxide
13161-30-3

2-hydroxy-pyridine N-oxide

4-methoxy-1-naphthoic acid chloride
70696-57-0

4-methoxy-1-naphthoic acid chloride

1-(4-methoxy-1-naphthoyloxy)-2-pyridone
390755-08-5

1-(4-methoxy-1-naphthoyloxy)-2-pyridone

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃;67%

13161-30-3Relevant articles and documents

Pattern of Addition of Hydroxyl Radicals to the Spin Traps α-Pyridyl 1-Oxide N-tert-Butyl Nitrone

Neta, P.,Steenken, S.,Janzen, Edward G.,Shetty, Raghav V.

, p. 532 - 534 (1980)

Hydroxyl radicals react with α-2, α-3, and α-4-pyridyl 1-oxide N-tert-butyl nitrones (POBN) with rate constants of 3.2E9, 4.8E9, and 3.5E9 M-1 s-1, respectively, via addition to two distinct sites.Addition to the pyridine ring yields short-lived radicals of the hydroxyazacyclohexadienyl type, while addition to the nitrone function in the side chain yields long-lived nitroxide radicals.The distribution of OH addition at the two molecular sites was determined by using differences in reducing power upon reaction of the different types of radicals with IrCl62-.The fraction of OH attack on the pyridine ring is ca. 0.6, relatively independent of the isomeric structure of the POBN.

Alkyl transfer with retention and inversion of configuration: Reexamination of a putative [1s,4s] sigmatropic rearrangement

Wolfe, Saul,Yang, Kiyull,Weinberg, Noham,Shi, Zheng,Hsieh, Yih-Huang,Sharma, Rajendra Dev,Ro, Stephen,Kim, Chan-Kyung

, p. 886 - 902 (1998)

The thermal rearrangement of 2-alkoxypyridine-1-oxides to 1-alkoxy-2-pyridones, which has been reported to proceed by an intramolecular [1s,4s] sigmatropic migration of the alkyl group with retention of configuration and first-order kinetics, has been reexamined. The intramolecular barriers have been computed to be at least 20 kcal mol-1 higher than the reported experimental barriers. An alternative bimolecular mechanism, discovered computationally, has been confirmed by a variety of experiments including crossover studies, determination of solvent effects and secondary H/D isotope effects, and new kinetic and stereochemical studies. In the new mechanism there is an initial intermolecular transfer of the alkyl group, with inversion of configuration, to the N-oxide. Depending on the nature of the alkyl group and the solvent, this is followed by a second transfer, also with inversion of configuration, of one of the alkyl groups of the cationic intermediate to one of the oxygens of the anionic intermediate. The product is then formed either without crossover, by a double inversion of one alkyl group, or with crossover by two single inversions of different alkyl groups. The proposed intermediates of this mechanism can be synthesized; they react to form a 1-alkoxy-2-pyridone at room temperature.

STIMULUS-TRIGGERED PRODRUGS

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Page/Page column 51-53, (2012/01/13)

Set forth herein, inter alia, are compositions and methods for treating diseases with prodrugs. Provided herein are prodrug compositions for inhibiting the function of proteins, compositions and methods for treating diseases associated with oxidative compounds, oxidatively-sensitive prodrugs of inhibitors of metalloproteases. and methods of inhibiting metalloproteases using oxidatively-sensitive prodrugs.

An efficient synthesis of heterocyclic N-oxides over molecular sieve catalyst

Prasad, M. Ramakrishna,Kamalakar, G.,Madhavi, G.,Kulkarni, S. J.,Raghavan, K. V.

, p. 1577 - 1578 (2007/10/03)

Heterocyclic N-oxides have been synthesized in very high yields over redox molecular sieve catalysts in the presence of H2O2.

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